Enstar Group Limited

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UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

_____________________________________

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of the

Securities Exchange Act of 1934

(Amendment No. )

_____________________________________


	Filed by the Registrant x		Filed by a Party other than the Registrant o
	Check the appropriate box:

o		Preliminary Proxy Statement

o		Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))

x		Definitive Proxy Statement

o		Definitive Additional Materials

o		Soliciting Material Pursuant to §240.14a-12

ENSTAR GROUP LIMITED

(Name of Registrant as Specified In Its Charter)

(Name of Person(s) Filing Proxy Statement, if other than the Registrant)

Payment of Filing Fee (Check the appropriate box):

No fee required.

Fee paid previously with preliminary materials.

Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11.

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Dear Fellow Shareholders: On behalf of Enstar Group Limited's Board of Directors, I am pleased to invite you to attend our 2023 Annual General Meeting of Shareholders, which will be held virtually on Thursday, June 1, 2023 at 9:00 a.m. Atlantic time, when we will vote on the matters described in the notice of the Annual General Meeting and the proxy statement. We had a solid 2022 in terms of our industry-leading Run-off Liability Earnings, or RLE, which indicates how well we extract value from the legacy portfolios we acquire. Our RLE grew to $756 million, driven by our ability to consistently drive better outcomes through claims management, or what we call the “Enstar Effect.” Conversely, unrealized investment losses during 2022 primarily caused by the rapid increase in interest rates more than offset the positive results of our core run-off business. However, we have previously noted that our investment assets provide liquidity for our policyholder liabilities as they come due. As such, we describe ourselves as being predominantly buy-and-hold investors, with the view that those unrealized losses will naturally reverse as the securities approach maturity and the investments recover to par value. In addition to our strong RLE performance, we were pleased to complete our biggest loss portfolio transfer acquisition ever with Aspen Insurance, increasing the number of claims we managed by about 40%. Through this deal and two others, we acquired $2.7 billion of incremental total liabilities last year; further validation that Enstar remains the legacy partner of choice for the world’s leading insurance groups. You can learn more about our successes during 2022 in advance of the meeting from our year-end video and Annual Report on Form 10-K. Against this backdrop, we maintain a long-term focus as a trusted strategic partner to the global insurance sector. We will continue to acquire and efficiently wind down legacy property/casualty risk portfolios. We have also evolved our governance and management. Following the declassification of our Board, all directorships expire in 2023, and all incumbents seek re-election on an annual basis. Meanwhile, we have adopted a fixed retirement age for directors, which is intended to preserve expertise through continuity, but also to encourage board turnover and refreshment. To better carry out the Board's objectives as Enstar grows, we have expanded the breadth and depth of our executive officer ranks, promoting highly experienced individuals and Enstar veterans who enhance our management skill set and ensure a beneficially more diverse range of views around the table. With this expanded leadership team, and in light of the insightful feedback we garnered from shareholders, the Human Resources and Compensation Committee has implemented changes to the structure of the executive annual incentive program, adding a corporate component and tying the financial component of the program to Adjusted Return on Equity as the sole financial metric. The Human Resources and Compensation Committee also extended the term of our CEO's long-term incentive award, ensuring he remains incentivized throughout his remaining contract term into 2025. In the context of Enstar’s ESG actions, for which the Board assumes ultimate responsibility, I am pleased to report significant progress following development of a formal ESG strategy last year. Details are disclosed in our second annual ESG report. Particular achievements include baselining our greenhouse gas emissions, recruiting our first Head of ESG, and beginning work to bring our investment holdings into line with our environmental and social responsibility, in part through implementing aggregate emissions and ESG rating limits within parts of our portfolio.

I encourage you to vote as soon as possible. You can do so over the internet, by telephone, or, if you received a proxy/voting instruction card, by marking, dating, and signing it, and returning it by mail. I hope you virtually attend the Annual General Meeting, and I thank you for your continued support of Enstar.

Sincerely, Robert J. Campbell Chairman of the Board

Notice of 2023 Annual

General Meeting of Shareholders


You are cordially invited to attend the annual general meeting of shareholders of Enstar Group Limited (the "Company"), on Thursday, June 1, 2023, at 9:00 a.m., Atlantic time (8:00 a.m. Eastern time). The annual general meeting of shareholders will be held as a virtual meeting only over live webcast, accessible at the following website address: www.virtualshareholdermeeting.com/ESGR2023. So long as you were a holder of record of the Company's voting ordinary shares as of the close of business on April 4, 2023, you or your proxy holder can attend, submit your questions, and vote your shares electronically at the annual general meeting by visiting the meeting website address and using your control number included in the proxy materials. During the meeting, you will be able to ask questions and will have the opportunity to vote to the same extent as you would at an in-person meeting of shareholders. To ensure that your vote is counted at the meeting, please vote as promptly as possible. Submitting your proxy now will not prevent you from voting your shares at the meeting if you desire to do so, as your vote by proxy is revocable at your option in the manner described in the proxy statement. By Order of the Board of Directors, Audrey B. Taranto General Counsel and Corporate Secretary Hamilton, Bermuda April 21, 2023 Important Notice Regarding the Availability of Proxy Materials for the Annual General Meeting of Shareholders to be held on June 1, 2023. This notice of meeting, the proxy statement, the proxy card and the annual report to shareholders for the year ended December 31, 2022 are available electronically at www.proxyvote.com/ESGR.

						Time and Date
						9:00 a.m. Atlantic time (8:00 a.m. Eastern time), on Thursday, June 1, 2023



						Meeting Website Address
						www.virtualshareholdermeeting.com/ESGR2023



						Items of Business
						■To vote on a proposal to elect twelve directors nominated by our Board to hold office until 2024 ■To hold an advisory vote to approve executive compensation ■To hold an advisory vote on the frequency of future advisory votes to approve executive compensation ■To ratify the appointment of PricewaterhouseCoopers LLP as our independent registered public accounting firm for 2023 and to authorize the Board, acting through the Audit Committee, to approve the fees for the independent registered public accounting firm



						Record Date
						Only holders of record of the Company's voting ordinary shares at the close of business on April 4, 2023 are entitled to notice of and to vote at our annual general meeting of shareholders, or any adjournments or postponements thereof

Table of Contents


Proxy Statement Summary			i
Annual General Meeting of Shareholders Information			i
2022 Business Highlights			ii
Executive Compensation			iii
Our Board of Directors			iv
Corporate Governance Highlights			v
Voting Matters and Vote Recommendations			vi

Corporate Governance			1
Proposal No. 1 – Election of Directors			1
Board Composition and Refreshment			2
Our Direc tor Nominees			4
Directorship Arrangements			12
Director Independence			13
Committees of the Board			14
Board and Committee Operations			18
Board Oversight of Risk Management			21
Environmental , Social and Governance Matters			24
Code of Conduct			25
Shareholder Engagement and Communications with our Board			25
Our Executive Officers			27
Direc tor Compensation			30

Executive Compensation			32
Proposal No. 2 – Advisory Vote to Approve Executive Compensation			32
Compensation Discussion and Analysis			33
Executive Compensation Tables			51
Equity Compensation Plan Information			62
Pay Versus Performance			62
CEO Pay Ratio			67
Proposal No. 3 – Say on Pay Frequency Vote			68

Audit Matters			69
Proposal No. 4 – Ratification of Appointment of Independent Registered Public Accounting Firm			69
Report of the Audit Committee			70
Change of Independent Registered Public Accounting Firm			70
Audit and Non-Audit Fees			71

Certain Relationships and Related-Party Transactions			73
Beneficial Ownership of Certain Holders			73
Certain Relationships and Related Transactions			76

Other Matters			81
Questions and Answers			81

Appendix A - Non-GAAP Financial Measures			A-1



In this proxy statement, the terms "Enstar," "we," "our," and "Company" refer to Enstar Group Limited. Information presented in the proxy statement is based on calendar years. The proxy statement includes website addresses and references to additional materials found on those websites. These websites and materials are not incorporated into the proxy statement by reference. These materials were first sent or made available to shareholders on April 21, 2023. Cautionary Statement Regarding Forward-Looking Statements This document contains certain forward-looking statements within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934 with respect to our financial condition, results of operations, business strategies, ESG objectives, operating efficiencies, competitive positions, growth opportunities, plans and objectives of our management, as well as the markets for our securities and the insurance and reinsurance sectors in general. Statements that include words such as "estimate," "project," "plan," "intend," "expect," "anticipate," "believe," "would," "should," "could," "seek," "may" and similar statements of a future or forward-looking nature identify forward-looking statements for purposes of the federal securities laws or otherwise. Forward-looking statements may appear throughout this proxy statement, including in the Chairman's letter and the Annual Incentive Program section of Compensation Discussion & Analysis. These statements include statements regarding the intent, belief or current expectations of Enstar and its management team. Investors are cautioned that any such forward-looking statements speak only as of the date they are made, are not guarantees of future performance and involve risks and uncertainties, and that actual results may differ materially from those projected in the forward-looking statements as a result of various factors. Important risk factors regarding Enstar can be found under the heading "Risk Factors" in our Annual Report on Form 10-K for the year ended December 31, 2022. Furthermore, Enstar undertakes no obligation to update any written or oral forward-looking statements or publicly announce any updates or revisions to any of the forward-looking statements contained herein, to reflect any change in its expectations with regard thereto or any change in events, conditions, circumstances or assumptions underlying such statements, except as required by law.

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

Proxy Statement
Summary

To assist you in reviewing our proxy statement, we have summarized several key topics below. The following description is only a summary and does not contain all of the information that you should consider before voting. For more complete information, you should carefully review the rest of our proxy statement, as well as our Annual Report to Shareholders for the year ended December 31, 2022.

ANNUAL GENERAL MEETING OF SHAREHOLDERS INFORMATION

WHEN

Thursday, June 1, 2023 at 9:00 a.m.

Atlantic time (8:00 a.m. Eastern time)

WHERE

The Annual General Meeting can be

accessed virtually via the Internet by visiting

www.virtualshareholdermeeting.com/ESGR2023

RECORD DATE

April 4, 2023

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VOTING

Your vote is very important and we urge you to

vote as soon as possible. See Question and

Answer No. 11 for voting instructions


			Enstar Group Limited / i / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

2022 BUSINESS HIGHLIGHTS

Enstar is a multi-faceted insurance group that offers innovative capital release solutions through its network of group companies in Bermuda, the United States, the United Kingdom, Continental Europe, Australia, and other international locations. In 2022, the Company successfully acquired $2.7 billion of incremental liabilities, including the industry’s third largest loss portfolio transfer agreement with Aspen Insurance Holdings. Our Run-off Liability Earnings were $756 million, driven by our ability to consistently drive better outcomes through claims management. However, our investment portfolio was impacted by the combination of interest rate increases, widening credit spreads and equity market declines, which drove us to incur a net loss attributable to Enstar ordinary shareholders of $906 million for 2022, largely due to net realized and unrealized investment losses of $1.6 billion. This result created a 25.2% decrease in our book value per share and return on equity of (15.6)%. As of December 31, 2022, our book value per share was $246.20. Despite the challenging financial result, the Company delivered on many key operational initiatives and is well-positioned for 2023. Select highlights of 2022 included:


			$3.9b
			Run-off transactions successfully completed in 2022 (including $1.2b of loss reserves previously assumed in an adverse development cover transaction with Aspen that were also subject to the $3.1b loss portfolio transfer with Aspen completed in 2022)


$756m			Run-off liability earnings for the year ended December 31, 2022

$19.5b			Total investable assets as of December 31, 2022

$14.8b

Total insurance liabilities as of December 31, 2022
(includes losses and loss adjustment expenses, future policyholder benefits, defendant A&E liabilities)

$37.2b

From inception, Enstar Group has completed or announced transactions to acquire $37.2b in loss reserves, future policy holder benefits acquired, and defendant and asbestos and environmental liabilities, and has successfully run-off $20.7b of those liabilities

$4.8b

Total shareholders' equity as of December 31, 2022

2022 PERFORMANCE VERSUS PEERS

*Source: Publicly filed financial information for peer company data. Peer group includes the companies selected as our peers by our Human Resources and Compensation Committee, as described in "Compensation Discussion & Analysis - Peer Group."


			Enstar Group Limited / ii / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

EXECUTIVE COMPENSATION

Our Executive Compensation Philosophy



We are a growing company operating in an extremely competitive and changing industry. Our compensation program is based on these core principles:
1	Incentivize performance consistent with clearly defined corporate objectives	3	Competitively compensate our executives
2	Align our executives’ long-term interests with those of our shareholders	4	Retain and attract qualified executives who are able to contribute to our long-term success

Key Compensation Decisions for 2022 Performance Year

Our Human Resources and Compensation Committee (the "Compensation Committee") made the following key compensation decisions:

Annual Incentive Awards:

Financial Component

Corporate Component

Individual Component

•The financial component for all executive officers scored "Below Threshold" as the threshold for Adjusted Return on Equity was not achieved.

•As a result, the financial component of the plan paid out at 0% of each executive's target opportunity and drove lower overall awards in 2022.

•The Compensation Committee evaluated the Company's performance against objectives designed to drive our medium to long-term strategic plan to determine an overall corporate component rating.

•The overall corporate component rating was achieved slightly above "target" level of opportunity.

•The Compensation Committee evaluated each executive based on a robust set of individual objectives, which take into consideration the Company's goals and operational priorities for the year.

•Individual objectives were achieved largely between "threshold" and "target" levels of opportunity.

Long-term Incentive Awards:

CEO

President / CFO

CSO / CCO

•Extended the term of our CEO's long-term incentive ("LTI") award, ensuring he remains incentivized throughout his remaining contract term into 2025.

•No new LTI awards were granted to these executive officers following grants made to them in 2020. The performance share unit ("PSU") portion of these 2020 awards vested at 0% due to financial performance below threshold.

•Granted annual LTI awards to the CSO and CCO consisting of 70% PSUs and 30% restricted share units ("RSUs").

•The CSO also received a special cliff-vesting RSU award during 2022 to address retention risk and in connection with his promotion.

Results of Say-on-Pay Vote

At last year's annual general meeting held on June 1, 2022, our shareholders approved the compensation of our executive officers with 75% of the total votes cast in favor of the proposal. The Compensation Committee strives for a higher level of shareholder approval, and we increased our engagement efforts to understand shareholder concerns and increase the dialogue between shareholders and Compensation Committee members. A table outlining shareholder feedback and our responses is set forth in "Executive Compensation - Compensation Discussion & Analysis - Results of Shareholder Vote on Compensation and Shareholder Engagement."


			Enstar Group Limited / iii / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

OUR BOARD OF DIRECTORS

The following describes our current Board composition and current committee assignments of each of our directors with ages and tenures calculated as of April 21, 2023.

Director Since

Other Public Board

Committee Membership

Name

Primary Occupation

Age

Independent

Non-Management Directors

B. Frederick Becker

Non-Executive Director

2015

Yes

Sharon A. Beesley

CEO, BeesMont Law Limited and BeesMont Consultancy Limited

2021

Yes

Robert Campbell (Chair)

Partner, Beck Mack & Oliver

2007

Yes

C E

James Carey

Managing Director, Stone Point Capital

2013

Susan L. Cross

Former Global Chief Actuary, XL Group (now AXA XL)

2020

Yes

Hans-Peter Gerhardt

Former CEO of Asia Capital Re, PARIS RE and AXA Re

2015

Yes

W. Myron Hendry

Former Executive Vice President and Chief Platform Officer, XL Group (now AXA XL)

2019

Yes

Paul O’Shea

Former President, Enstar Group Limited

2001

Hitesh Patel

Non-Executive Director

2015

Yes

Poul Winslow

Former Senior Managing Director,
Canada Pension Plan Investment Board

2015

Yes

Management Directors

Orla Gregory

President, Enstar Group Limited

2022

Dominic Silvester

CEO, Enstar Group Limited

2001

C = Committee Chair AC = Audit Committee RC = Risk Committee

E = Audit Committee Financial Expert HC = Human Resources and Compensation Committee IC = Investment Committee

= Committee Member NC = Nominating and Governance Committee EC = Executive Committee

Range of Tenures

Mix of Ages

Independent Oversight

45-59

5-10

60-65

8 of 12 independent directors

>10

66+

Average Tenure:

Average Age:

4 of 6 independent committees

9.1 Years

64.3 Years


			Enstar Group Limited / iv / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

CORPORATE GOVERNANCE HIGHLIGHTS

Enstar operates under a corporate governance framework designed to be a flexible working structure for principled actions, effective decision-making, and appropriate monitoring of both compliance and performance. Our key governance documents, including our Corporate Governance Guidelines, are available at https://www.enstargroup.com/corporate-governance.



Annual director elections			All directors are elected annually for a one-year term.
Majority voting			We have a majority voting standard in uncontested elections of directors.
Independent oversight			Eight of our twelve directors are independent. Our Audit Committee, Human Resources and Compensation Committee, Nominating and Governance Committee, and Risk Committee are entirely independent.
Independent Board leadership			Our CEO is focused on managing Enstar and our independent Board Chair drives accountability at the Board level. Each of our Board committees are led by independent directors.
Executive sessions			All quarterly Board meetings include executive sessions of independent directors.
Share ownership guidelines			We have robust share ownership guidelines for our directors and executive officers.
Shareholder engagement			We have an annual shareholder engagement program that solicits feedback from shareholders and proxy advisory firms on various matters such as corporate governance, our compensation programs, and sustainability.
Access to management			Our Board has significant interaction with senior management and access to other employees.
Time commitment policy			Our Corporate Governance Guidelines prohibit directors from serving on more than three public company boards without the permission of our Board Chair. None of our current directors serve on the board of more than one other publicly traded company.
Succession planning			Our Board regularly reviews Board and executive succession planning.
Board, committee, and individual self-evaluations			Our Board, committees, and individual directors conduct annual performance self-evaluations led by our independent Board Chair, including one-on-one interviews.
Director orientation, continuing education and training			We have established multi-faceted orientation, continuing education and training programs for our directors, overseen by our Nominating and Governance Committee.
Clawback and prohibition on hedging			We have a stringent Clawback Policy applicable to directors and executives. We also prohibit hedging of Company shares.
No poison pill			We do not have a shareholder rights plan, commonly known as a "poison pill."


			Enstar Group Limited / v / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

VOTING MATTERS AND VOTE RECOMMENDATIONS

Proposals

Board Recommendation and Page Reference

Election of twelve directors nominated by our Board to hold office until 2024

•Our Board is made up of directors with diverse skills, qualities, attributes, and experiences to effectively address the Company's evolving needs and represent the best interests of the Company's shareholders.

•Eight of our twelve nominees are independent, and four of our twelve nominees identify as women and/or racially/ethnically diverse.

The Board recommends a vote FOR each director nominee

Further information beginning on page 1

Advisory vote to approve executive compensation

•Our executive compensation program is designed to align pay with performance, taking into account shareholder feedback and interests.

•The compensation paid to our named executive officers in 2022 reflected our financial results and share price performance.

The Board recommends a vote FOR this proposal

Further information beginning on page 32

Advisory vote on the frequency of future advisory votes to approve executive compensation

•Our shareholders currently have the opportunity to participate annually in an advisory vote of our executive compensation.

•Say on Pay advisory votes should be conducted each year so that our shareholders can annually express their views on our executive compensation program.

The Board recommends a vote of ONE YEAR for this proposal

Further information beginning on page 68

Ratification of the appointment of PricewaterhouseCoopers LLP as our independent registered public accounting firm for 2023 and authorization for the Board, acting through the Audit Committee, to approve the fees for the independent registered public accounting firm

•PricewaterhouseCoopers LLP is an independent registered public accounting firm with the required knowledge and experience to effectively audit the Company's financial statements.

•Audit and non-audit services are pre-approved by the Audit Committee, which is composed entirely of independent directors, each of which qualify as audit committee financial experts.

The Board recommends a vote FOR this proposal

Further information beginning on page 69


			Enstar Group Limited / vi / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

Corporate
Governance

Proposal 1:

Election of Directors

WHAT AM I VOTING ON?

The Board of Directors, upon the recommendation of the Nominating and Governance Committee, has nominated the following twelve individuals for election to the Board for a one-year term. If elected, each Director nominee will hold office until the 2024 Annual General Meeting of Shareholders or, if earlier, until his or her resignation or removal.

■Robert J. Campbell

■Susan L. Cross

■Paul J. O'Shea

■B. Frederick Becker

■Hans-Peter Gerhardt

■Hitesh Patel

■Sharon A. Beesley

■Orla Gregory

■Dominic Silvester

■James D. Carey

■Myron Hendry

■Poul A. Winslow

The Board recommends a vote FOR each nominee

All of the nominees are currently serving as directors, and their biographies are presented below under "Biographies of Director Nominees." Included in each nominee’s biography is an assessment of his or her specific qualifications, attributes, skills, and experience. The nominees were selected following the recommendation by our Nominating and Governance Committee, a committee comprised entirely of independent directors. Each nominee has consented to serve if elected. We do not expect that any nominee will become unavailable for election as a director, but if a nominee should become unavailable prior to the meeting, the proxies to vote for such nominee will instead either be voted for a substitute nominee recommended by our Board, or not voted, if the Board determines in its discretion that the position should remain vacant.

We recently completed the process of declassifying our Board after shareholders approved management's proposal to transition to one-year terms for our directors. As a result, all directors are now elected to one-year terms. If elected at the 2023 annual general meeting, each director will hold office until the Company's 2024 annual general meeting or, if earlier, until his or her resignation or removal.


			Enstar Group Limited / 1 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

BOARD COMPOSITION AND REFRESHMENT

Our Board is made up of a diverse group of leaders with substantial experience in their respective fields. Our Board believes that the combination of the various skills, qualifications and experiences of its directors contributes to an effective and well-functioning Board and that, individually and as a whole, its directors possess the necessary qualifications to provide effective oversight and insightful strategic guidance.

We continually review our Board’s composition to identify the skills needed for our Company both in the near term and into the future. Board succession planning and annual reviews of Board composition by the Nominating and Governance Committee assure that the Board continues to maintain an appropriate mix of objectivity, skills and experiences to provide fresh perspectives and effective oversight and guidance to management, while leveraging the institutional knowledge and historical perspective of our longer-tenured directors. The most recent addition to the Board was Orla M. Gregory, who was appointed in February 2022. Ms. Gregory is also our President, and she brings extensive industry experience and a deep knowledge of the Company's operations to our Board.

The Board believes that refreshment is important to help ensure that Board composition is aligned with the needs of the Company and the Board as our business evolves over time, and that fresh viewpoints and perspectives are regularly considered. The Board also believes that over time directors develop an understanding of the Company and an ability to work effectively as a group.

Directors are elected each year, at the annual general meeting of shareholders, to hold office until the next annual general meeting of shareholders or, if earlier, until their resignation or removal. Because term limits could cause the loss of experience or expertise important to the optimal operation of the Board, there are no limits on the number of terms that a director may serve, but the Nominating and Governance Committee and the Board consider the tenure of directors as one of several factors in nomination decisions. To promote refreshment, the Board established a retirement age of eighty for non-employee directors in 2022 following a comprehensive director succession planning exercise conducted by our Nominating and Governance Committee.

Board Membership Criteria

The Board and the Nominating and Governance Committee believe that there are general qualifications that all directors must exhibit and other key qualifications and experiences that should be represented on the Board as a whole but not necessarily by each individual director. Given the complex nature of our business and the insurance and reinsurance industry, we seek directors whose experiences, although varying and diverse, are also complementary to and demonstrate a familiarity with the substantive matters necessary to lead the Company and navigate our business.

Qualifications Required of All Directors

The Board and the Nominating and Governance Committee require that each director possess high personal and professional integrity and character, strong business judgement, the ability to represent the interests of the Company's shareholders, knowledge regarding insurance, reinsurance and investment matters, as well as other factors discussed below.

Key Qualifications and Experiences to be Represented on the Board

The Board has identified key qualifications and experiences that are important to be represented on the Board as a whole, in light of the Company's business strategy and expected future business needs. The Board reviews these categories from time to time, alongside its consideration of whether there are new areas that would benefit it in executing its oversight duties. The table set out on page 5 summarizes these key qualifications and how they are linked to our Company's business.

Consideration of Board Diversity

We seek to identify candidates who represent a mix of backgrounds and experiences that will improve the Board’s ability, as a whole, to serve our needs and the interests of our shareholders. In February 2019, the Board adopted a


			Enstar Group Limited / 2 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

formal diversity policy applicable to the selection of directors. The Board considers diversity to include self-identified gender, self-identified ethnicity, nationality, age, self-identified sexual orientation, geographic background, and other personal characteristics whether self-identified or otherwise. Our Board Diversity Policy requires the Nominating and Governance Committee to actively consider diversity in its regular assessments of board composition and in its efforts to identify potential director candidates, including specifically requiring that one or more female, underrepresented minority or LGBTQ+ candidates be included in formal searches for new directors.

The Board assesses the effectiveness of its diversity policy every year through our Board and committee evaluation process and annual composition review. Where potential improvements are identified, the Nominating and Governance Committee may propose changes to the policy to enhance its effectiveness. Board diversity has also been a key topic in our annual shareholder engagement discussions. In response to shareholder feedback and upon recommendation from the Nominating and Governance Committee, the Board amended its diversity policy in 2021 to strengthen its commitment to improving diversity amongst its members by imposing aspirational diversity targets.

As provided in the revised policy, the Board endeavors to maintain diversity amongst its members such that at least 30% of the Board will comprise persons who self-identify as female or as an underrepresented minority or LGBTQ+. On gender diversity specifically, the Board is committed to maintaining at least three female Board members and over time will aim to reach and maintain a minimum of at least 30% female representation on the Board. For purposes of these targets, an underrepresented minority is a person who self-identifies within one or more of the following categories that have been established by the U.S. Equal Employment Opportunity Commission: Black or African American, Hispanic or Latinx, Asian, Native American or Alaska Native, Native Hawaiian or Other Pacific Islander or two or more races or ethnicities.

Following the recent appointments of Mmes. Beesley and Gregory, 33% of our Board comprises persons who self-identify as female or as an underrepresented minority, and three, or 25%, self-identify as female. The Board intends to continue to improve its overall diversity over time without further increases to its size, unless otherwise determined appropriate by our Board.

Evaluation and Nomination of Director Candidates

Primary responsibility for identifying and evaluating director candidates and for recommending the re-nomination of incumbent directors resides with the Nominating and Governance Committee, which consists entirely of independent directors under applicable SEC rules and Nasdaq listing standards. Our Board Chair also shares some responsibility for new director recruitment, including the responsibility of working with our CEO, Nominating and Governance Committee and the full Board to help identify and prioritize the specific skill sets, experience, and knowledge that director candidates must possess. The Nominating and Governance Committee, with input from our Board Chair, then establishes the criteria for director nominees based on these inputs, which are outlined under the subheadings, "Qualifications Required of All Directors" and "Key Qualifications and Experiences to be Represented on the Board" above.

Nomination of New Candidates

Potential director candidates meeting the criteria established by the Nominating and Governance Committee and adopted by the full Board have primarily been identified through the periodic solicitation of recommendations from members of the Board and individuals known to the Board, the use of third-party search firms retained by the Nominating and Governance Committee, and shareholders; however, in certain private placement or acquisition-related transactions, parties have obtained the right to designate a board representative. The Nominating and Governance Committee is authorized, at the Company's expense, to retain search firms to identify potential director candidates, as well as other external advisors, including for purposes of performing background reviews of potential candidates. Search firms retained by the Nominating and Governance Committee are provided guidance as to the particular experience, skills, or other characteristics that the Board is then seeking. The Nominating and Governance Committee may delegate responsibility for day-to-day management and oversight of a search firm engagement to its Chair, any one or more of its members, the Board's Chair, and/or appropriate members of management with the Nominating and Governance Committee's oversight.

The evaluation of new director candidates involves several steps performed on a rolling basis and not always taken in order. The Nominating and Governance Committee reviews and verifies the candidate's qualifications and


			Enstar Group Limited / 3 / 2023 Proxy Statement			Table of Contents

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Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

background information and evaluates the candidate's attributes relative to the identified needs of the Board. If the Nominating and Governance Committee wishes to pursue a candidate further, it arranges candidate interviews with committee members and other members of the Board and certain executive officers to ensure that candidates not only possess the requisite skills and characteristics, but also the personality, leadership traits, work ethic, and independence of thought to contribute effectively as a member of the Board. After assessing the feedback, the Nominating and Governance Committee presents each selected candidate to the Board for consideration. The Board then nominates successful candidates for election to the Board at the Annual General Meeting. Director candidates are principally identified and evaluated in anticipation of upcoming director elections and other potential or expected Board vacancies. From time to time, the Board may create and fill vacancies in its membership which arise between annual meetings of shareholders using the process described above.

Re-nomination of Incumbents

To ensure that the Board continues to evolve in a manner that serves the changing business and strategic needs of the Company, before recommending for re-nomination a slate of incumbent directors for an additional term, the Nominating and Governance Committee also evaluates each incumbent director’s overall service to the Company during the director’s term including the director’s level of participation and quality of performance, and whether the incumbent directors possess the requisite skills and perspective, both individually and collectively. This evaluation is based primarily on the results of the annual review it performs with the Board of the requisite skills and characteristics of Board members, the composition of the Board as a whole, and the results of the Board’s annual self-evaluation and individual director evaluations. The Nominating and Governance Committee considered and nominated the candidates proposed for election as directors at the Annual General Meeting, with the Board unanimously agreeing on the nominees.

Shareholder Recommendations

In accordance with its charter, the Nominating and Governance Committee will consider director candidates submitted by shareholders. Shareholders may recommend candidates to serve as directors by submitting a written notice to the Nominating and Governance Committee at Enstar Group Limited, P.O. Box HM 2267, Windsor Place, 3rd Floor, 22 Queen Street, Hamilton, HM JX, Bermuda. Shareholder recommendations must be accompanied by sufficient information to assess the candidate’s qualifications and contain the candidate’s consent to serve as a director if elected. Shareholder nominees will be evaluated by the Nominating and Governance Committee in the same manner as nominees it selects itself.

OUR DIRECTOR NOMINEES

Each of our nominees are currently serving as directors. The Board believes that all of its directors have demonstrated professional integrity, ability and judgment, as well as strategic management and oversight abilities, and have each performed well in their respective time served as directors and contributed to the overall effectiveness of our Board.

The following matrix highlights the mix of key skills, qualities, attributes, and experiences of the nominees that, among other factors, led the Board and the Nominating and Governance Committee to recommend these nominees for election to the Board. The matrix is intended to depict notable qualifications and skills for each director in which they specifically declare expertise or leading experience in, and not having a mark does not mean that a particular director does not possess that qualification or skill. Nominees have developed competencies in these skills through education, direct experience, and oversight responsibilities. The demographic information presented below is based on voluntary self-identification by each nominee. Additional details on each nominee's experiences, qualifications, skills, and attributes are set forth in their biographies beginning on page 5. The categories listed under the "Skills and Experience" column in the matrix below are those key qualifications and experiences our Board believes should be represented on the Board and are summarized in the table immediately following the matrix together with how they are linked to our business. Further details regarding the independence of our directors including determinations of independence for each are set out fully under the section heading, "Independence of Directors" below.


			Enstar Group Limited / 4 / 2023 Proxy Statement			Table of Contents

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Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

Director Skills and Demographic Matrix


Skills and Experience
	Extensive Insurance Industry Experience
	Risk Management
	Finance and Accounting
	Investment
	Strategy
	Corporate Governance
	Regulatory and Government
	Business Operations and Technology
	Human Capital Management
Tenure and Independence
	Tenure (years)	8	2	16	9	3	8	1	4	21	8	21	8
	Independence
Demographics
	Age (years)	76	66	74	56	63	67	49	74	65	62	62	57
	Gender Identity	M	F	M	M	F	M	F	M	M	M	M	M
	African American or Black
	Alaskan Native or American Indian
	Asian
	Hispanic or Latinx
	Native Hawaiian or Pacific Islander
	White
	Two or More Races or Ethnicities
	LGBTQ+


			Enstar Group Limited / 5 / 2023 Proxy Statement			Table of Contents

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Executive Compensation

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Other Matters


Extensive Insurance Industry Experience Extensive experience within the insurance industry including in executive, director or other leadership roles at major insurance institutions. Our Board believes representation of this experience is important as our business is a specialized global enterprise operating within a complex and highly regulated industry.
Risk Management Experience related to establishing risk appetite levels and risk management processes for operations, acquisitions, underwriting, and investment portfolios. Our Board believes representation of this skill is important as the Board is responsible for overseeing the various risks facing the Company and ensuring that appropriate policies and procedures are in place to effectively manage risk.
Finance and Accounting Experience related to developing and understanding finance and capital management needs in line with corporate strategies, as well as financial reporting, audit and actuarial-related expertise. Our Board believes representation of this skill is important as the Company’s business is multifaceted and involves complex financial and insurance transactions in many countries subject to various regulatory prudential standards.
Investment Expertise related to assessing large and complex investment portfolios and determining investment strategies in line with delineated risk appetites. Our Board believes representation of this skill is important as the Company’s investment portfolio continues to grow in size and complexity, with investable assets totaling $19.5 billion as of December 31, 2022.
Strategy Experience challenging management on setting and/or adjusting business strategies, including acquisitions, divestitures, operations, and investments. Our Board believes representation of this skill is important as the Company’s long-term success is dependent on setting and executing a responsible corporate strategy and the continuous review of strategic transactions.
Corporate Governance A practical understanding of developing and championing governance procedures and protections that drive Board and management accountability and protection of shareholder interests, including ESG knowledge and advocacy. Our Board believes representation of this skill is important as the size, nature and complexity of the Company's business presents both opportunities and challenges to advancing our sustainability initiatives, and requires an appropriately designed corporate governance framework to protect the interests of the Company's stakeholders.
Regulatory and Government A deep understanding of the highly regulated environment in which we operate, and the ever-changing regulations and requirements that govern our operations and shape our future strategies. Our Board believes representation of this skill is important as the Company’s business requires compliance with a variety of regulatory requirements across a number of countries and the ability to maintain relationships with various governmental entities and regulators.
Business Operations and Technology A practical understanding of developing, implementing, and assessing business operations, processes, information systems, technology and associated risks, including information security and cybersecurity. Our Board believes representation of this skill is important as the Company's scale and complexity requires aligning many areas of our operations, including integration of new businesses, technology, and human resources, while remaining innovative and adaptable in an increasingly digital society.
Human Capital Management Experience managing a large and/or global workforce and recruiting and retaining talent. Our Board believes representation of this skill is important as the Company's global workforce represents one of our key resources.

Biographies of Director Nominees

Below is biographical information about our director nominees describing each director nominee's qualifications and relevant experience. The biographies include key qualifications, skills, and attributes most relevant to the decision to nominate candidates to serve on the Board. This information is current as of the date of this proxy statement and has been confirmed by each of the director nominees for inclusion in this proxy statement.


			Enstar Group Limited / 6 / 2023 Proxy Statement			Table of Contents

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Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters



			B. Frederick "Rick" Becker Independent Biographical Information Rick Becker has 40 years of experience in the insurance and healthcare industries. He served as Chairman of Clarity Group, Inc., a company he co-founded more than 18 years ago that specialized as a healthcare professional liability and risk management service provider until it was sold in early 2020. Prior to co-founding Clarity Group, Inc., he served as Chairman and Chief Executive Officer of MMI Companies, Inc. from 1985 until its sale to The St. Paul Companies in 2000. Mr. Becker has previously served as President and CEO of Ideal Mutual and McDonough Caperton Employee Benefits, Inc., and also served as State Compensation Commissioner for the State of West Virginia. He began his career as a practicing attorney. Skills and Qualifications Compensation, governance, and risk management experience; industry knowledge. Mr. Becker has over 40 years of experience within the insurance and healthcare industries. The Board also values Mr. Becker’s corporate governance experience, which he has gained from serving on many other boards over the years. In addition, his previous work on compensation matters makes him well-suited to serve as Chairman of our Human Resources and Compensation Committee. He has an extensive background in risk management, which enhances our risk oversight and monitoring capabilities.


Director Since: 2015 Age: 76 Enstar Committees: Audit, Human Resources and Compensation (Chair), Nominating and Governance (Chair) US resident; US citizen



			Sharon A. Beesley Independent Biographical Information Ms. Beesley currently serves as the Chief Executive Officer and senior partner of BeesMont Law Limited, a Bermuda-based commercial law firm, which she established in 2008. She also serves as Chief Executive Officer of BeesMont Consultancy Limited, a Bermuda-based consultancy business, a position she has held since 2000. Ms. Beesley previously served as a Director on the Board of the Bermuda Monetary Authority from 2016 to 2021. Prior to 2000, Ms. Beesley was engaged in private legal practice in Bermuda and other international jurisdictions. Skills and Qualifications Legal expertise; regulatory and government experience; corporate governance Ms. Beesley brings to our Board her multi-jurisdictional legal expertise, strategic and risk management perspectives, gained from over 40 years of experience in the legal and financial services industry advising on all areas of corporate law, investment funds, structured finance, joint venture structures, and mergers and acquisitions as a Solicitor in England and Wales, Hong Kong, and as a practicing Barrister and Attorney of the Bermuda Bar. In addition, Ms. Beesley's experience as a former director of our insurance group supervisor, the Bermuda Monetary Authority, is particularly valuable to our Board as we manage increasingly complex compliance, regulatory and governance matters.



Director Since: 2021 Age: 66 Enstar Committees: Nominating and Governance Bermuda resident; British, Canadian and Irish citizen


			Enstar Group Limited / 7 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters



			Robert Campbell Chairman, Independent Biographical Information Robert Campbell was appointed as the independent Chairman of the Board in November 2011. Mr. Campbell has been a Partner with the investment advisory firm of Beck, Mack & Oliver, LLC since 1990. Certain Other Directorships Mr. Campbell is a director and chairman of the audit committee of AgroFresh Solutions, Inc. (formerly Boulevard Acquisition Corp.), a publicly traded global agricultural technologies company. From 2015 through 2017, he was also a director of Boulevard Acquisition Corp. II, a blank check company that completed its initial public offering in September 2015. He previously served as a director of Camden National Corporation, a publicly traded company, from 1999 to 2014. Skills and Qualifications Financial, accounting, and investment expertise; leadership skills Mr. Campbell brings to the Board his extensive understanding of finance and accounting, which he obtained through over 40 years of analyzing financial services companies and which is very valuable in his role as chairman of our Audit Committee. In addition, Mr. Campbell's investment management expertise makes him a key member of our Investment Committee, of which he serves as chairman. Mr. Campbell continues to spend considerable time and energy in his role, which is significant to the leadership and function of our Board.


Director Since: 2007 Age: 74 Enstar Committees: Audit (Chair), Human Resources and Compensation, Investment (Chair), Nominating and Governance, Executive (Chair) US resident; US citizen



			James Carey Non-Employee Biographical Information James Carey is a Managing Director of Stone Point Capital LLC, a private equity firm based in Greenwich, Connecticut. Stone Point Capital serves as the manager of the Trident Funds, which invest exclusively in the global financial services industry. Mr. Carey has been with Stone Point Capital and its predecessor entities since 1997. He previously served as a director of the Company from its formation in 2001 until the Company became publicly traded in 2007. Mr. Carey rejoined the Board in 2013. Certain Other Directorships From July 2018, Mr. Carey has served as a director of Focus Financial Partners, a publicly traded company that invests in independent fiduciary wealth management firms. Mr. Carey also currently serves on the boards of certain privately held portfolio companies of the Trident Funds. He previously served as non-executive chairman of PARIS RE Holdings Limited and as a director of Alterra Capital Holdings Limited, Cunningham Lindsay Group Limited, Lockton International Holdings Limited, and Privilege Underwriters, Inc. Skills and Qualifications Investment expertise; industry knowledge; significant acquisition experience Having worked in the private equity business for over 20 years, Mr. Carey brings an extensive background and expertise in the insurance and financial services industries. His in-depth knowledge of investments and investment strategies is significant in his role on our Investment Committee. We also value his contributions as an experienced director in the insurance industry, as well as his extensive knowledge of the Company.


Director Since: 2013 Age: 56 Enstar Committees: Investment US resident; US citizen


			Enstar Group Limited / 8 / 2023 Proxy Statement			Table of Contents

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Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters



			Susan L. Cross Independent Biographical Information Susan L. Cross has served as a director since October 2020. She served as Executive Vice President and Global Chief Actuary at XL Group (now AXA XL), from 2008 to 2018, and prior to that served as Senior Vice President and Chief Actuary of various operating segments since 1999. Certain Other Directorships Ms. Cross currently serves as a non-executive director at Unum Group, a Fortune 500 publicly held insurance company and leading provider of financial protection benefits, where she sits on the Audit Committee and Risk and Finance Committee. Previously, she has served on the boards of IFG Companies, American Strategic Insurance and several XL subsidiaries, including Mid Ocean Limited and XL Life Ltd. Skills and Qualifications Actuarial expertise; risk management, regulatory and governance skills; industry experience Ms. Cross brings significant actuarial expertise to our Board, obtained from over 20 years of senior management experience as an actuary with XL Group. Her industry experience is particularly valuable to our Audit Committee and our Risk Committee given the complex nature of our run-off business. As a director of a Fortune 500 company, Ms. Cross also has knowledge of corporate governance matters and practices, which is valuable to our Board.


Director Since: 2020 Age: 63 Enstar Committees: Audit, Risk US resident; US citizen



			Hans-Peter Gerhardt Independent Biographical Information Hans-Peter Gerhardt served as the Chief Executive Officer of Asia Capital Reinsurance Group from October 2015 through June 2017. He has served continuously in the reinsurance industry since 1981. He is the former Chief Executive Officer of PARIS RE Holdings Limited, serving in that position from the company's initial formation in 2006 through the completion of its merger into Partner Re Ltd. in June 2010. He previously served as the Chief Executive Officer of AXA Re from 2003 to 2006, also serving as Chairman of AXA Liabilities Managers, the AXA Group's run-off operation, during that time. Certain Other Directorships Mr. Gerhardt served as a non-executive director of StarStone Holdings Ltd. and of African Risk Capacity (all privately held). He previously served as a non-executive director of Tokio Millenium Re and Tokio Marine Kiln as well as Asia Capital Reinsurance Group (until May 2017) and as an independent director of Brit Insurance Holdings PLC until the company's acquisition by Fairfax Financial Holdings in 2015. Skills and Qualifications Underwriting expertise; proven industry veteran Mr. Gerhardt brings decades of underwriting expertise to our Board. He is a proven industry veteran, with significant leadership experience, including several successful tenures in CEO roles.


Director Since: 2015 Age: 67 Enstar Committees: Risk, Human Resources and Compensation, Executive Swiss resident; German citizen


			Enstar Group Limited / 9 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters



			Orla Gregory President, Director Biographical Information Orla Gregory was appointed President of the Company in March 2023. She previously served as Chief Financial Officer from September 2021 to March 2023 and served as our Chief Operating Officer since 2016. Since joining us in 2003, Ms. Gregory has held increasingly senior roles, including Chief Integration Officer from 2015 to 2016, Executive Vice President of Mergers and Acquisitions of our subsidiary, Enstar Limited, from 2014 to 2015, Senior Vice President of Mergers and Acquisitions from 2009 to 2014, and Financial Controller from 2003 to 2009. Ms. Gregory previously served as a Financial Controller of Irish European Reinsurance Company Ltd. in Ireland, an Investment Accountant with Ernst & Young Bermuda, and as a Financial Accountant for QBE Insurance & Reinsurance (Europe) Limited. Skills and Qualifications Company leader; finance & accounting; operations and technology; human capital management; industry expertise Ms. Gregory is a qualified chartered accountant and experienced company executive who has spent more than 27 years in the insurance and reinsurance industry, including 18 years with our Company. As Company President, Ms. Gregory brings to our Board intimate knowledge and expertise regarding the Company and our industry. Her experience developing and managing the Company's operations and global workforce is particularly valuable to our Board in light of the Company's strategic focus on human capital management.


Director Since: 2022 Age: 49 Enstar Officer Title: President Bermuda resident; Irish citizen



			Willard Myron Hendry, Jr Independent Biographical Information Myron Hendry most recently served as an executive advisor to AXA on integration matters. He previously served as the Executive Vice President and Chief Platform Officer for XL Catlin from 2009-2018, where he was responsible, on a Global basis, for Technology, Operations, Real Estate, Procurement, Continuous Improvement Programs and XL Catlin's Service Centers in India and Poland. He also served as Director on the XL India Business Services Private Limited Board, and he was the Chairman of the XL Catlin Corporate Crisis Committee responsible for Disaster Recovery and Business Continuity. Mr. Hendry was the founder of the XL Catlin's Leadership Listening Program. Throughout his career, he also held technology, operational and claims leadership roles at Bank of America's Balboa Insurance Group, Safeco Insurance and CNA Insurance. Skills and Qualifications Operations and Technology Mr. Hendry brings to our Board expertise in insurance industry-specific information technology and operations management. His extensive experience as an executive engaging on technology matters at the board level is valuable to our Board and Risk Committee.


Director Since: 2019 Age: 74 Enstar Committees: Nominating and Governance, Risk US resident; US citizen


			Enstar Group Limited / 10 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters



			Paul O'Shea Non-Employee Biographical Information Paul O’Shea retired as President of the Company in March 2023. He had been appointed as President in December 2016. He previously served as Executive Vice President and Joint Chief Operating Officer of the Company since our formation in 2001 and has also been a director throughout this time. He has led our mergers and acquisitions operations, including overseeing our transaction sourcing, due diligence, and negotiations processes. In 1994, Mr. O’Shea joined Dominic Silvester in his run-off business venture in Bermuda, and he served as a director and Executive Vice President of Enstar Limited, which is now a subsidiary of the Company, from 1995 until 2001. Prior to co-founding the Company, he served as the Executive Vice President, Chief Operating Officer and a director of Belvedere Group/Caliban Group from 1985 until 1994. Certain Other Directorships Mr. O'Shea serves as the Company's director representative on the board of directors of Core Specialty Holdings, a privately held property casualty insurer. Skills and Qualifications Company leader; long track record of successful acquisitions; industry expertise Mr. O’Shea is a qualified chartered accountant who has spent more than 30 years in the insurance and reinsurance industry, including many years in senior management roles. As a co-founder of the Company, Mr. O’Shea has intimate knowledge and expertise regarding the Company and our industry. He has been instrumental in sourcing, negotiating and completing numerous significant transactions since our formation.


Director Since: 2001 Age: 65 Bermuda resident; Irish citizen



			Hitesh Patel Independent Biographical Information Hitesh Patel is an Independent Non-Executive director who serves on boards of a number of financial services companies. He served as Chief Executive Officer of Lucida, plc, a UK life insurance company, from 2012 to 2013, and prior to that as its Finance Director and Chief Investment Officer since 2007. Mr. Patel has over 30 years of experience working in the insurance industry, having served in the United Kingdom as KPMG LLP's Lead Partner on Insurance Accounting and Regulatory Services from 2000 to 2007. He originally joined KPMG in 1982 and trained as an auditor. Certain Other Directorships Mr. Patel is the Independent Non-Executive Chairman of Capital Home Loans Limited, a privately held buy-to-let mortgage provider and also a non-executive director of Landmark Mortgages Limited and Augusta Ventures Holdings Limited which provides litigation finance. Until December 2019, Mr. Patel served as a non-executive director at Aviva Life Holdings UK Ltd and Aviva Insurance Limited (subsidiaries of Aviva plc) and as Chairman of its Audit Committee and member of the Risk and Investment Committees. Skills and Qualifications Accounting expertise; regulatory and governance skills; industry experience Mr. Patel brings significant accounting expertise to our Board, obtained from over two decades of auditing and advising insurance companies on accounting and regulatory issues, which is highly valuable to our Audit Committee. As a former industry CEO, he also has significant knowledge of risk management best practices, corporate governance matters, and the insurance regulatory environment, which are valuable to our Board, the Risk Committee, and the Nominating and Governance Committee.


Director Since: 2015 Age: 62 Enstar Committees: Audit, Nominating and Governance, Risk (Chair) UK resident; UK citizen


			Enstar Group Limited / 11 / 2023 Proxy Statement			Table of Contents

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Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters



			Dominic Silvester Chief Executive Officer, Director Biographical Information Dominic Silvester has served as a director and the Chief Executive Officer of the Company since its formation in 2001. In 1993, Mr. Silvester began a business venture in Bermuda to provide run-off services to the insurance and reinsurance industry. In 1995, the business was assumed by Enstar Limited, which is now a subsidiary of the Company, and for which Mr. Silvester has since then served as Chief Executive Officer. Prior to co-founding the Company, Mr. Silvester served as the Chief Financial Officer of Anchor Underwriting Managers Limited from 1988 until 1993. Skills and Qualifications Company leader; industry expertise; corporate strategy As a co-founder and CEO of the Company, Mr. Silvester contributes to the Board his intimate knowledge of the Company and the run-off industry. He is well known in the industry and is primarily responsible for identifying and developing our business strategies and acquisition opportunities on a worldwide basis. Mr. Silvester has served as our CEO since the Company's inception, demonstrating his proven ability to manage and grow the business.


Director Since: 2001 Age: 62 Enstar Committees: Investment, Executive Bermuda resident; UK citizen



			Poul Winslow Independent Biographical Information Poul Winslow retired in May 2022 as Senior Managing Director & Global Head of Capital Markets and Factor Investing of the Canada Pension Plan Investment Board ("CPP Investments"), a role he had held since 2018. Previously Mr. Winslow served as Head of External Portfolio Management and Head of Thematic Investing for CPP Investments. Prior to joining CPP Investments in 2009, Mr. Winslow had several senior management and investment roles at Nordea Investment Management in Denmark, Sweden and the United States. He also served as the Chief Investment Officer of Andra AP-Fonden (AP2) in Sweden. Despite his retirement from CPP Investments, Mr. Winslow remains CPP Investments' designated director representative. Certain Other Directorships Mr. Winslow served as a director for the Standards Board for Alternative Investments, an international standard-setting body for the alternative investment industry, until June 2022. He previously served as a director of Viking Cruises Ltd., a private company, from 2016 to 2018. Skills and Qualifications Investment expertise; compensation and governance experience Mr. Winslow brings significant investment expertise to our Board gained from his years in senior investment roles, which is highly valuable to our Investment Committee as it oversees our investment strategies and portfolios. His experiences at CPP Investments, including exposure to compensation and governance policies, are valuable in his role on our Compensation Committee.


Director Since: 2015 Age: 56 Enstar Committees: Human Resources and Compensation, Investment, Executive Canadian resident; Canadian and Danish citizen

DIRECTORSHIP ARRANGEMENTS

On June 3, 2015, CPP Investments purchased 1,501,211 shares of Enstar from fund partnerships that had acquired shares as consideration in one of our acquisitions. In connection with the 2015 transaction: (i) the selling shareholders' rights terminated; and (ii) we and CPP Investments entered into a new Shareholder Rights Agreement granting CPP Investments contractual shareholder rights that were substantially similar to those rights previously


			Enstar Group Limited / 12 / 2023 Proxy Statement			Table of Contents

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Executive Compensation

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Other Matters

held by the selling shareholders, including the right to designate one representative to our Board. CPP Investments designated Poul Winslow as a director of the Company, and he was appointed in September 2015. On May 2, 2022, Mr. Winslow retired from CPP Investments, but he continues to serve as the designated director representative of CPP Investments. The designation right terminates if CPP Investments ceases to beneficially own at least 75% of the total number of voting shares and Series E Non-Voting Shares shares acquired by it in the original transaction. CPP Investments subsequently acquired additional shares, including through CPPIB Epsilon Ontario Limited Partnership. Following the repurchase by the Company of all of its non-voting shares held by CPP Investments on March 28, 2023, CPP Investments holds 9.4% of Enstar’s outstanding voting ordinary shares and remains contractually entitled to appoint a director representative on the Company's board of directors.

DIRECTOR INDEPENDENCE

Our Board currently consists of twelve directors, of which ten are non-employee directors, and eight are independent. The Company's Corporate Governance Guidelines provide, and our Board believes, that a majority of its members should be independent directors who meet the criteria for independence required by the Nasdaq listing standards, as determined by the Board. The Charters of our Audit Committee, Human Resources and Compensation Committee, and Nominating and Governance Committee also require that every member of such committees meet the criteria for independence required by the Nasdaq listing standards, as determined by the Board, and in certain instances, enhanced independence standards within the meaning of SEC rules. These requirements are included in the Corporate Governance Guidelines and the committee charters, which are available at www.enstargroup.com under "Investor Relations" — "Corporate Governance."

Independence Assessment

To assess independence, the Nominating and Governance Committee and the Board review the independence of each director at the time of their appointment and no less than annually thereafter. For a director to be considered independent, the Board must determine that the director meets the definition of independence included in Nasdaq Marketplace Rule 5605(a)(2). This requires a determination that the director does not have any direct or indirect material relationship with us, which in the opinion of the Board, would interfere with the exercise of independent judgment in carrying out the responsibilities of a director. In making such determination, the Nominating and Governance Committee and the Board consider all known relevant facts and circumstances, including but not limited to the director’s commercial, industrial, banking, consulting, legal, accounting, investment, charitable and familial relationships known or reported to us in connection with the preparation of this proxy statement or otherwise.

In making their independence determination, the Nominating and Governance Committee and the Board specifically considered the following transaction during 2022 and concluded it did not impair any director's independence:

•Upon the recommendation of an independent broker, one of our subsidiaries leases a corporate apartment in a building in Bermuda that is owned by a company in which Ms. Cross and her spouse hold a 40% interest, and in which Ms. Cross's spouse serves as President. Ms. Cross was not involved in the sourcing or negotiations of the transaction. This transaction involved dollar amounts below the amounts that would preclude a finding of independence under Nasdaq listing standards or qualify it as a related party transaction.

Consistent with these considerations and based on the report and recommendation of the Nominating and Governance Committee, the Board affirmatively determined that:

▪Messrs. Campbell, Becker, Gerhardt, Hendry, Patel, and Winslow and Mmes. Beesley, and Cross qualify as non-employee directors within the meaning of Rule 16b-3 under the Securities Exchange Act of 1934, as amended (the "Exchange Act"), and are independent within the meaning of Nasdaq Marketplace Rule 5605(a)(2);

▪Messrs. Campbell, Becker, and Patel and Ms. Cross meet the enhanced independence standards defined in Nasdaq Marketplace Rule 5605(c)(2) and Rule 10A-3(b) of the Exchange Act, with respect to members of the Audit Committee;


			Enstar Group Limited / 13 / 2023 Proxy Statement			Table of Contents

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Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

▪Messrs. Campbell, Becker, Gerhardt, and Winslow meet the enhanced independence standards defined in Nasdaq Marketplace Rule 5605(d)(2)(A) and Rule 10C-1(b)(1)(ii)(A) and (B) of the Exchange Act, with respect to members of the Human Resources and Compensation Committee;

▪Mr. Carey is a non-employee director within the meaning of Rule 16b-3 under the Exchange Act, but is not independent within the meaning of Nasdaq Marketplace Rule 5605(a)(2) due to matters described under "Certain Relationships and Related Transactions" beginning on page 76 of this proxy statement;

▪Mr. O'Shea is a non-employee director within the meaning of Rule 16b-3 under the Exchange Act, but is not independent within the meaning of Nasdaq Marketplace Rule 5605(a)(2) due to his recent service with us as an executive officer; and

▪Mr. Silvester and Ms. Gregory are management directors and are not independent due to their service with us as executive officers.

For details about certain relationships and transactions among us and our executive officers and directors, see "Certain Relationships and Related Transactions."

COMMITTEES OF THE BOARD

Our Board has six standing committees: the Audit Committee, the Human Resources and Compensation Committee, the Nominating and Governance Committee, the Risk Committee, the Investment Committee, and the Executive Committee. Details of the composition and primary responsibilities of each of the Board's standing committees are summarized in the sections titled "Committee Membership" and "Information about our Committees" below.

Committee Membership

The Board appoints members of its committees annually, with the Nominating and Governance Committee reviewing and recommending committee membership. Interim changes to committee membership may be made by the Board, upon recommendation from the Nominating and Governance Committee, following director appointments, resignations, or periodic reviews considering the changing needs of our business or Board. When determining committee composition and leadership, both the Nominating and Governance Committee and the Board may consider a variety of factors including: committee composition requirements set out in each committee's charter, individual director experience and qualifications, director independence, time commitments and constraints, the results of previous Board or committee evaluations, director tenure, succession planning and refreshment needs, diversity, and such other factors as thought appropriate from time to time.

Information About Our Committees

Our committees operate under written charters that have been approved by the Board, and each Committee reviews its charter annually and recommends any proposed changes to the Board. Current copies of the charters for all of our committees are available on our website at http://www.enstargroup.com/corporate-governance. In addition, any shareholder may receive copies of these documents in print, without charge, by contacting the Corporate Secretary at P.O. Box HM 2267, Windsor Place, 3rd Floor, 22 Queen Street, Hamilton, HM JX, Bermuda. The primary responsibilities of each of our committees are described below.


			Enstar Group Limited / 14 / 2023 Proxy Statement			Table of Contents

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Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

Audit Committee

CHAIR(1)

MEMBERS(1)

MEETINGS HELD

IN 2022:

INDEPENDENCE

Robert

Campbell

B. Frederick Becker

Susan L. Cross

Hitesh
Patel

4 out of 4

2022 Highlights

The Committee approved and supported the Company's change of independent registered public accounting firms from KPMG Audit Limited to PricewaterhouseCoopers LLP.

Primary Responsibilities

▪Overseeing our accounting and financial reporting process, including our internal controls over financial reporting.

▪Overseeing the quality and integrity of our financial statements.

▪Engaging and overseeing the Company's independent registered public accounting firm (taking into account the vote on shareholder ratification) and considering the independence, qualifications and performance of our independent auditors.

▪Pre-approving compensation, fees and services of our independent auditors and reviewing the scope and results of their audit.

▪Reviewing the performance of our internal audit function.

▪Reviewing, and where appropriate approving, our internal audit function's audit plan, staffing, budget, responsibilities and performance.

▪Reviewing all related party transactions.

▪Periodically reviewing our risk exposures and the adequacy of our controls over such exposures in coordination with our Risk Committee.

▪Periodically reviewing the adequacy and effectiveness of the controls and procedures (including the level of assurance) applicable to our key ESG disclosures.

Additional Information

The Audit Committee's Report is set forth beginning on page 70 of this proxy statement.

(1)The Board has determined that all members of the Committee satisfy the criteria adopted by the SEC to serve as "audit committee financial experts."

Human Resources and Compensation Committee

CHAIR(1)

MEMBERS(1)

MEETINGS HELD

IN 2022:

INDEPENDENCE

B. Frederick

Becker

Robert Campbell

Hans-Peter Gerhardt

Poul
Winslow

4 out of 4

2022 Highlights

The Committee adopted a balanced scorecard approach for our Annual Incentive Plan and increased its involvement in human capital and resources strategy, development and monitoring, including quarterly meetings with the Chief People Officer.

Primary Responsibilities

▪Overseeing policies and strategies relating to talent, leadership and culture, including diversity, equity, and inclusion.

▪Overseeing our management development and succession plans and processes.

▪Determining the compensation of our executive officers.

▪Establishing our compensation philosophy.

▪Overseeing the development and implementation of our compensation programs, including our incentive plans and equity plans.

▪Overseeing the risks associated with the design and operation of our compensation programs, policies and practices.

▪Periodically reviewing the compensation of our directors and making recommendations to our Board with respect to the adequacy and structure of compensation.

▪Maintaining sole authority to retain, terminate and approve fees and other terms of engagement of its compensation consultant and to obtain advice and assistance from internal or external legal, accounting or other advisors.

Additional Information

Additional information on the Human Resources and Compensation Committee and the role of management in setting compensation is provided below in "Executive Compensation - Compensation Discussion and Analysis."

(1)The Board has determined that all members of the Committee satisfy Nasdaq Enhanced Independence Requirements for Compensation Committee Members.


			Enstar Group Limited / 15 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

Nominating and Governance Committee

CHAIR

MEMBERS

MEETINGS HELD

IN 2022:

INDEPENDENCE

B. Frederick

Becker

Sharon A. Beesley

Robert Campbell

W. Myron Hendry

Hitesh
Patel

5 out of 5

2022 Highlights

In 2022, the Committee enhanced the Board evaluation process by implementing individual director performance reviews and supplementing the use of written questionnaires with one-on-one interviews between directors and our Board Chair. Individual performance results were considered during the director nomination process.

Primary Responsibilities

▪Establishing and overseeing the group’s organizational, governance and communication structures and confirming the operating effectiveness of each.

▪Establishing director qualification criteria; identifying individuals qualified to become directors; and reviewing any candidates proposed by directors, management or shareholders for appointment or reappointment to the Board.

▪Overseeing our Board succession planning process, and recommending annual director nominees to the Board and the Company's shareholders.

▪Reviewing the composition and function of the Board and its committees; recommending changes thereto; and recommending committee and leadership appointments to the Board.

▪Overseeing the annual evaluation of the performance and effectiveness of the Board and its committees, and making any recommendations for improvement.

▪Reviewing the composition and effectiveness of the group's material subsidiary boards, and overseeing their adherence to the group's established governance and communication frameworks.

▪Advising the Board with respect to corporate governance-related matters.

Risk Committee

CHAIR

MEMBERS

MEETINGS HELD

IN 2022:

INDEPENDENCE

Hitesh

Patel

Susan L. Cross

Hans-Peter Gerhardt

W. Myron
Hendry

4 out of 4

2022 Highlights

Under the Committee's oversight, we released our our inaugural set of formal ESG disclosures and enhanced our management of ESG risks by expanding our suite of ESG-related metrics. The Committee oversaw in-depth risk reviews of key topics (inflation and people risk) and ongoing enhancement of our Risk Appetite Framework including investment and ESG risks.

Primary Responsibilities

▪Assisting the Board in overseeing the integrity and effectiveness of the Company's Enterprise Risk Management framework.

▪Reviewing and evaluating the risks to which we are exposed, as well as monitoring and overseeing the guidelines and policies that govern the processes by which we identify, assess, and manage our exposure to risk.

▪Reviewing and monitoring our overall risk strategy and Board-approved risk appetite and overseeing any significant mitigating actions required.

▪Reviewing the Company’s forward-looking risk and solvency assessment and capital management.

▪Periodically reviewing and approving the level of risk assumed in underwriting, investment and operational activities.

▪Reviewing and monitoring the potential impact of emerging risks.

▪Overseeing the Company’s ESG risks, strategies, policies, programs and practices.

Additional Information

Additional information regarding the Risk Committee and the Board's oversight of risk is provided below under the Section titled "Board Oversight of Risk" beginning on page 21.


			Enstar Group Limited / 16 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

Investment Committee

CHAIR

MEMBERS

MEETINGS HELD

IN 2022:

INDEPENDENCE

Robert

Campbell

James
Carey

Dominic
Silvester

Poul
Winslow

2 out of 4

2022 Highlights

The Committee assessed Enstar's strategic asset allocation against an investment market backdrop marked by persistently higher inflation and interest rates. In support of our ESG strategy, the Committee enhanced our ESG oversight policies in relation to our external asset manager monitoring process.

Primary Responsibilities

▪Determining our investment strategy.

▪Developing and reviewing our investment policies and guidelines and overseeing compliance with these guidelines and various regulatory requirements.

▪Overseeing our investments, including approval of investment transactions.

▪Reviewing and monitoring the Company’s investment performance quarterly and annually against plan and external benchmarks agreed from time to time.

▪Overseeing the selection, retention and evaluation of outside investment managers.

▪Overseeing investment-related risks, including those related to the Company's cash and investment portfolios and investment strategies.

▪Overseeing our internal investment management function.

▪Coordinating with other committees of the Board to assist with the implementation of the Company's ESG strategy.

▪Reviewing and approving the Company's use of derivatives.

Executive Committee

CHAIR

MEMBERS

MEETINGS HELD

IN 2022:

INDEPENDENCE

Robert

Campbell

Hans-Peter Gerhardt

Dominic
Silvester

Poul
Winslow

3 out of 4

2022 Highlights

Because our full Board was able to meet throughout the year as needed, the Committee was not required to convene any meetings in 2022. Our Board reviewed the Committee's charter in 2022, and determined that the Committee's purpose and composition remain appropriate for the effective functioning of the Board.

Primary Responsibilities

▪To exercise the power and authority of the Board when the entire Board is not available to meet, except that the Executive Committee may not authorize the following:

–the issuance of equity securities of the Company;

–the merger, amalgamation, or other change in control transaction of the company;

–the sale of all or substantially all of the assets of the Company;

–the liquidation or dissolution of the Company;

–any transaction that, in the aggregate, exceeds 10% of the Company's total assets;

–any action that requires approval of the entire Board by the Company's Memorandum of Association or the Company's Bye-laws; or

–any action prescribed by applicable law, rule or regulation, including but not limited to those prescribed by listing rules or SEC regulations (such as those powers granted to the Compensation, Audit, and Nominating and Governance Committees and requiring independent director decisions).


			Enstar Group Limited / 17 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

BOARD AND COMMITTEE OPERATIONS

Board Leadership Structure

Our Board is supportive of objective, independent leadership for itself and each of its committees. Our Board views the active, objective, independent oversight of management as central to effective Board governance, to serving the best interests of our Company and our shareholders, and to executing our strategic objectives and creating long-term value. This support is exemplified in our Board's track record of: maintaining separate roles of Board Chair and Chief Executive Officer since 2011, appointing an independent director to serve as our Board's Chair for the last decade, and appointing independent directors to serve as chairs of each of the Board's committees for the last six years.

Independent Board Leadership

The Board is currently led by an independent director, Robert Campbell, who has served as its Chair since 2011. Our Bye-laws and Corporate Governance Guidelines permit the roles of Board Chair and Chief Executive Officer to be filled by the same or different individuals, although our Board continues to express a preference for the separation of the two roles. This flexibility allows the Board to determine whether the two roles should be combined or separated based upon our Company's evolving needs, strategy, operating environment, shareholder input, and the Board’s assessment of its leadership from time to time.

The Board believes that our shareholders are best served at this time by having an independent director serve as Chair. Our Board believes this leadership structure effectively allocates authority, responsibility, and oversight between management and the independent members of our Board. It gives primary responsibility for the operational leadership and strategic direction of the Company to our Chief Executive Officer, while the Chair facilitates our Board’s independent oversight of management, promotes communication between senior management and our Board about issues such as company strategy and performance, leadership team development, succession planning, and executive compensation. Our Chair engages with shareholders, and supports the Board's Nominating and Governance Committee's consideration of key governance matters.

The Board recognizes, however, that no single leadership model is right for all companies at all times and that, depending on the circumstances in the future, other leadership models might be appropriate for us. In the event our Board leadership model should change and our Board Chair were to no longer be independent, our Corporate Governance Guidelines provide an established Board Chair succession plan whereby the independent members of the Board will designate an independent director to act as the Lead Independent Director with clearly delineated responsibilities to ensure a minimum level of independent Board leadership is maintained.


			Enstar Group Limited / 18 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

Duties of our Board Chair

The following table outlines the key functions and responsibilities of our Board Chair.



Board Leadership •Presiding at meetings of the Board, including executive sessions of the independent directors •Calling meetings of the Board •Soliciting views and feedback from all Board members and prompting engagement
Board Priorities •Focusing on key issues and tasks facing our Company, and on topics of interest to our Board •Contributing to the annual performance review of the CEO, and participating in succession planning with our Human Resources and Compensation Committee
Board Culture •Serving as a liaison between the CEO and executive management team and the Board •Encouraging rigorous review, debate and challenge •Providing support, advice, and feedback from our Board to the CEO while respecting executive responsibility •Assisting our Board, Nominating and Governance Committee, and management in complying with our Corporate Governance Guidelines and promoting corporate governance best practices
Board Performance and Development •Promoting the efficient and effective performance and functioning of our Board •Consulting with our Nominating and Governance Committee on our Board's annual self-evaluation •Preparing improvement plans to address areas identified during self-evaluation process and monitor progress •With our Nominating and Governance Committee, consulting in the identification and evaluation of director candidates' qualifications and consulting on committee membership and committee chairs
Board Meetings •Planning, reviewing, and approving meeting agendas for our Board •Approving meeting schedules to provide for sufficient time for discussion of agenda items •Advising the CEO and management of the information needs of our Board •Developing topics of discussion for executive sessions of our Board
Shareholders and Other Stakeholders •Consulting and directly communicating with shareholders and other key constituents, as appropriate •Leading annual shareholder engagement program to discuss executive compensation and corporate governance matters •Being available for communication with our primary regulators (with or without management present) to discuss the appropriateness of our Board’s oversight of management and our Company

Director Attendance at Meetings

We expect our directors to attend our annual general meeting of shareholders as well as all meetings of the Board and each committee on which they serve, absent extraordinary circumstances. In 2022, our Board held five meetings and its committees held 24 meetings in aggregate, for a combined total of 29 Board and committee meetings. No incumbent director attended fewer than 75% of the total number of Board and applicable committee meetings held during the year ended December 31, 2022, in each case during the period that such director served.


			Enstar Group Limited / 19 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

In addition, all directors serving on our Board at the time of our 2022 annual general meeting of shareholders attended the meeting.

Our independent directors also meet privately in executive session led by the Board Chair on a regular basis without our CEO or other members of management present.

Director Orientation and Continuing Education

We have a comprehensive orientation program for all new directors. This orientation program includes one-on-one meetings with senior management, visits to our headquarters when possible, and extensive written materials to familiarize new directors with our business, financial performance, strategic plans, director and executive compensation programs, and corporate governance policies and practices.

We also offer continuing education to assist directors in enhancing their skills and knowledge to better perform their duties and to recognize, and deal appropriately with, issues that may arise. These programs may be part of regular Board and committee meetings or provided by qualified third parties on various topics. In addition, the Company pays for all reasonable expenses for any director who wishes to attend an external director continuing education program approved by the Board's Chair.

Board and Committee Evaluations

The Board recognizes that a robust and constructive evaluation process is an essential component of good corporate governance and Board effectiveness. Under the leadership of, and in consultation with, Board and committee Chairs, the Nominating and Governance Committee oversees the annual Board and committee evaluation process as well as the development and monitoring of any remediation plans.

Evaluation Process and Incorporation of Feedback

Our Board and each of its committees conduct separate annual self-evaluations. Each director evaluates the Board, the committees on which he or she serves, and individual director performance. Our annual evaluations typically cover areas such as: Board and committee efficiency and overall effectiveness; Board and committee composition and structure; performance of Board and committee leadership; director performance; strategic and performance abilities; Board and committee interaction with management; and quality of Board and committee meetings and materials. An overview of our annual Board and committee evaluation process is described below.



Determine Scope, Focus Areas, and Format			The formal self-evaluation may be in the form of written or oral questions administered by Board members, management, or third parties. Each year, our Nominating and Governance Committee, with input from Board and committee Chairs, discusses and considers the appropriate approach, including areas of focus, scope and format, and approves the selected evaluations.
Conduct Evaluation			Members of our Board and each of its committees participate in the formal evaluation process, responding to questions designed to elicit information to be used in improving Board and committee effectiveness and individual director performance. In 2022, our Board evaluation was administered via written questionnaires supplemented by one-on-one interviews between each director and the Board Chair.
Review Feedback			Director feedback solicited from the formal self-evaluation process is discussed during Board and committee meetings and, where appropriate, addressed with individual directors and/or management.
Respond to Director Input			In response to feedback from the evaluation process, our Board and committees work to improve the effectiveness of their policies, processes, and procedures. Recent examples include enhancements to meeting materials and agenda topics, committee responsibilities, committee reports to the Board, the Board evaluation process, director on-boarding, director continuing education, and management interaction.


			Enstar Group Limited / 20 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

BOARD OVERSIGHT OF RISK MANAGEMENT

Risk Management

Inherent in the Board’s responsibilities is an understanding of and effective oversight over the various risks facing the Company. The Board does not view risk in isolation. The Board recognizes that it is neither possible nor prudent to eliminate all risk. Indeed, purposeful and appropriate risk taking is essential for the Company to be competitive on a global basis and to achieve the Company’s long-term strategic objectives. Ensuring appropriate governance structures, processes and procedures are in place to provide for effective risk management that is aligned with strategy and embedded throughout our operations is fundamental to the Board. This facilitates:

▪understanding critical risks in the Company’s business and strategy;

▪allocating responsibilities for risk oversight among the full Board and its committees;

▪evaluating the Company’s risk management processes and whether they are functioning adequately;

▪facilitating open communication between management and Directors; and

▪fostering an appropriate culture of integrity and risk awareness.

Our Risk Governance Documents

We are committed to responsible and rigorous risk management and through a comprehensive approach with a defined Enterprise Risk Management Framework ("ERM Framework") and Risk Appetite Framework (collectively, our "ERM Program"). Management and the Board regularly review the ERM Framework and Risk Appetite Framework to promote continuous enhancement and improvement. The ERM Framework sets forth roles, responsibilities, and accountability for the management of risk and describes how our Board oversees the establishment of our risk appetite, including both quantitative limits and qualitative statements and objectives for our activities. This framework of objective, independent Board oversight and management’s robust risk management better enables us to serve our clients, deliver long-term value for our shareholders, and achieve our strategic objectives.

Our ERM Framework serves as the foundation for consistent and effective risk management. It outlines the key risks that our Company faces: strategic risk, capital adequacy risk, acquisition/transaction risk, reserving risk, investment risk, liquidity risk, foreign exchange risk, credit/counterparty risk, operational risk, regulatory risk, tax risk, and ESG risk. It describes components of our risk management approach, including our culture of effectively managing risk, risk appetite, risk management processes, and risk management governance structure.

Our Risk Appetite Framework defines the aggregate levels and types of risk our Board and management believe appropriate to achieve our Company’s strategic objectives and business plans.

Our Risk Governance Structure

The Board, with the assistance of its committees, reviews and oversees our ERM Program, including management's implementation of the same. Our risk governance structure is designed to complement our Board’s commitment to maintaining an objective, independent Board and committee leadership structure, and to fostering integrity over risk management throughout our Company.

A summary of our risk governance structure is set out below. Further details of our Company’s risk management policies, practices and framework are described in "Item. 1 Business - Enterprise Risk Management" of our Annual Report on Form 10-K for the year ended December 31, 2022.


			Enstar Group Limited / 21 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters




Board of Directors Our Board provides objective, independent oversight of risk and: ▪Receives regular updates from our Risk Committee and other Board committees, providing our Board with integrated, thorough insight about how our company manages risk. ▪Receives regular risk reporting from management including a report that provides updates on how key and emerging risks are being identified, assessed and mitigated. This includes comprehensive independent risk reviews of strategic initiatives (e.g. acquisitions). ▪Periodically holds stand-alone sessions at (and between) Board meetings to discuss the risks that are considered prevailing or urgent, including those identified in management’s report on key risks. Examples of key risk stand-alone discussion topics include risks related to information security, cybersecurity, sustainability, and human capital management (including diversity, equity and inclusion). ▪Oversees senior management’s development and implementation of our ERM Framework, our Risk Appetite Framework, and our capital, strategic, and financial operating plans. ▪Oversees directly and through committees our financial performance, execution against capital, strategic, and financial operating plans, compliance with risk appetite parameters, and the adequacy of internal controls, each of which our management monitors. ▪Directly oversees legal and compliance risk, and regularly receives updates from management on legal and compliance risk-related matters such as those arising from litigation. ▪Considers risk when reviewing material transactions and in connection with strategic planning and other matters. ▪Reviews and approves our ERM Framework and Risk Appetite Framework annually or more frequently in connection with material changes in the Company's risk profile.						Risk Committee Our Risk Committee has primary committee responsibility for overseeing the ERM Framework, our overall risk appetite, and material risks facing our company. The Committee regularly receives updates from management on risk-related matters and risk reporting from management and management risk committees, including a report that addresses and provides updates on key and emerging risks. The Committee also oversees senior management’s development of our ERM Framework and Risk Appetite Framework, and management’s alignment of our risk profile to our capital, strategic and operating plans. In addition, our Risk Committee approves our ERM Framework and Risk Appetite Framework on an annual basis and recommends them to the Board for approval.
						Audit Committee Our Audit Committee oversees the Company's internal controls over financial reporting. The Committee receives direct reports on internal controls from the Company’s Internal Audit leadership, who meets with the Committee on a quarterly basis and maintains an open dialogue with the Committee's Chair.
						Human Resources and Compensation Committee Our Human Resources and Compensation Committee oversees the development of our compensation policies and practices, which are designed to balance risk and reward in a way that does not encourage unnecessary or excessive risk-taking by our employees. The Committee also oversees and supports the Board in management succession planning.
						Nominating and Governance Committee Our Nominating and Governance Committee provides additional risk management oversight for corporate governance matters, including with respect to reviewing Board and Committee composition, and the Company’s relations with shareholders.
						Investment Committee Our Investment Committee provides additional risk management oversight for investment risk. The Committee regularly evaluates and tests the Company's investment portfolio and investment strategies under various stress scenarios, oversees compliance with investment guidelines (which assists the Company in monitoring its investment-related risks), and it monitors and evaluates the Company's internal investment management department and external investment managers.

Role of Management While the Board and its committees oversee the ERM Program, the Company's Risk Management function, headed by the Group Chief Risk Officer ("CRO"), is responsible for designing and operationalizing the various components of the ERM Framework throughout the group. The Company has robust internal processes and an effective internal control environment that facilitates the identification and management of risks and regular communication with the Board. This includes an enterprise risk management system utilizing a 'Three Lines Model' with the first line comprising management designed and owned processes and controls, the second line comprising various risk, controls and compliance oversight functions established by management, and the third line comprising independent assurance from our Internal Audit function. Management communicates routinely with the Board, Board committees and individual directors on the significant risks identified and how they are being managed. To ensure independence, our CRO reports to the CEO and has direct access to the Chair of our Risk Committee. Additionally, our CRO participates in Board, Risk Committee, Audit Committee, and Investment Committee meetings. Our Head of Internal Audit also reports directly to the Audit Committee.


			Enstar Group Limited / 22 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

Selected Areas of Oversight



			SPOTLIGHT ON: INTERNAL CONTROLS AND PROCEDURES The Board’s risk governance framework supports the Audit Committee’s oversight of the Company’s internal controls and procedures. Our internal control system is supported by a program of internal audits and appropriate reviews, written policies and guidelines, and compliance training.
			SPOTLIGHT ON: INFORMATION SECURITY The Board, directly and through the Risk Committee, also maintains oversight over information security and cybersecurity risk. The Risk Committee receives and provides feedback on updates from management each quarter regarding information security and cybersecurity governance processes, the status of projects to strengthen internal information security and cybersecurity and also discuss any significant information or cyber incidents, including recent incidents throughout the industry and the emerging threat landscape.
			SPOTLIGHT ON: ENVIRONMENT The Risk Committee oversees the management of long-term risks posed by climate change, including specific actions performed or to be performed to address the risks that climate changes poses to the Company. In addition, the Risk Committee reviews our sustainability programs and goals related to determining and reducing our climate impact in our operations and monitors our progress toward achieving such goals.
			SPOTLIGHT ON: HUMAN CAPITAL MANAGEMENT The Board is actively engaged in overseeing senior management development and succession as well as the Company’s key human capital management strategies. The Human Resources and Compensation Committee oversees succession planning, talent optimization initiatives, HR strategy, incentive compensation, and progress related to diversity, equity and inclusion. The Nominating and Governance Committee oversees director succession planning. Both committees provide reports and feedback to the full Board for its collective review and discussion.


			Enstar Group Limited / 23 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

ENVIRONMENTAL, SOCIAL AND GOVERNANCE MATTERS

Enstar has long emphasized corporate responsibility. Engagement with our shareholders has demonstrated that, although interest in ESG issues has existed for quite some time, there is a growing trend towards greater oversight, integration and reporting by companies on these issues. Many of the shareholders have expressed an interest in learning more about our ESG initiatives. We have placed increased emphasis on the importance of ESG to deliver the Company’s strategy for the benefit of its shareholders while recognizing our role in the wider community, and providing stakeholders with regular and transparent reporting regarding the Company's ESG impacts. We are in the process of publishing our second annual ESG Report, Sustainability (SASB) Report, and Climate Change (TCFD) Report, and our inaugural Diversity, Equity, and Inclusion ("DEI") Report. These disclosures will reflect the continuing progress of our ESG journey. For more information regarding our ESG initiatives and related matters or to obtain copies our annual ESG reports, please visit the “Sustainability” section of our corporate website.

ESG Strategy

Enstar's ESG strategy is informed by a materiality assessment, and focused on three primary areas:

https://cdn.kscope.io/710f0519bfdcb9809d742d39034164a5-Proxy World Image.jpg

Addressing Climate Change

Understand and mitigate the three major types of climate risk which may affect the sustainability of our business including insurance contracts we may assume.

Sustainable

Investing

Explore and improve the sustainable impact of our investment activities while maintaining our objective of obtaining the highest possible level of risk-adjusted investment returns consistent with the preservation of capital, liquidity, and prudent diversification.

https://cdn.kscope.io/710f0519bfdcb9809d742d39034164a5-Proxy HCM Image.jpg

Developing our Human Capital

Support a diverse, equitable and inclusive workforce to become an employer of choice that draws strength, opportunities, and financial growth from the diversity of our workforce.

2022 ESG Highlights

Select achievements from our 2022 ESG program are highlighted below:

https://cdn.kscope.io/710f0519bfdcb9809d742d39034164a5-Proxy Report Image.jpg

We strengthened our ESG reporting and risk management processes and are in the process of publishing our inaugural DEI Report.

We baselined our greenhouse gas emissions, allowing us to track, manage and work towards reducing them over time.

https://cdn.kscope.io/710f0519bfdcb9809d742d39034164a5-ESG Head.jpg

We recruited our first Head of ESG to continue driving our ESG strategy forward.

https://cdn.kscope.io/710f0519bfdcb9809d742d39034164a5-DEI2.jpg

We developed a long-term DEI vision, mission, and strategy, complete with five-year objectives across five strategic pillars.


			Enstar Group Limited / 24 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

CODE OF CONDUCT

We have adopted a Code of Conduct that applies to all of our directors and employees, including all senior executives and financial officers. A copy of our Code of Conduct is available on our website at http://www.enstargroup.com/corporate-governance by clicking on "Code of Conduct."

In addition, any shareholder may receive a copy of the Code of Conduct or any of our committee charters in print, without charge, by contacting Investor Relations at Enstar Group Limited, P.O. Box HM 2267, Windsor Place, 3rd Floor, 22 Queen Street, Hamilton HM JX, Bermuda. We intend to post any amendments to our Code of Conduct on our website. In addition, we intend to disclose any waiver of a provision of the Code of Conduct that applies to our senior executives and financial officers by posting such information on our website or by filing a Form 8-K with the SEC within the prescribed time period. No such waivers currently exist.

SHAREHOLDER ENGAGEMENT AND COMMUNICATIONS WITH OUR BOARD

Shareholder Engagement

In an effort to continuously augment our corporate governance and compensation processes and communications, we participate in annual engagements with our diverse shareholder base in an effort to foster long-term relationships with all of our investors and maintain channels for open communication as a means of sharing two-way feedback.

In addition, we consistently seek feedback from the investment community to share with our management team and Board to deepen their understanding of shareholder concerns.

Shareholder Engagement Cycle

Summer

Fall

Winter

Spring

•Hold annual shareholder meeting which is conducted virtually and easily accessible to all shareholders given our location in Bermuda.

•Board reviews vote outcomes of annual shareholder meeting.

•Board considers potential corporate governance or executive compensation changes.

•Consider potential topics of discussion in preparation for annual shareholder engagement and proxy advisor meetings.

•On occasion, we may engage with certain shareholders or proxy advisory firms off-cycle.

•We use the feedback from discussions with shareholders and proxy advisors in considering changes to governance and compensation practices.

•Launch formal annual engagement program targeting shareholders that hold approximately 1% or more of our outstanding voting shares and proxy advisory firms to engage in discussions about our governance and compensation practices.

•Publish proxy statement and disclosure based on shareholder and proxy advisor feedback.

•Begin preparations for annual shareholder meeting.


			Enstar Group Limited / 25 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

Shareholder Engagement in Practice

Led by our Board Chair (Mr. Campbell) and the Chair of both the Human Resources and Compensation Committee and the Nominating and Governance Committee (Mr. Becker), we spoke with several shareholders in 2023 representing approximately 38% of our outstanding voting ordinary shares as of December 31, 2022 and invited conversations with additional significant shareholders representing approximately 9% of our outstanding voting ordinary shares, who advised that they did not feel a need to meet with us this year. We also spoke to two major proxy advisory firms. Directors whose firms represent an additional 14% of our outstanding voting ordinary shares as of December 31, 2022 are actively involved in our Board's oversight of compensation and governance matters, and were not included in the engagement program.

Topics discussed in engagement meetings with shareholders typically include governance practices, board composition and effectiveness, executive compensation, and our ESG program. The results of our shareholder engagement program are shared with the Board, our Human Resources and Compensation Committee, and our Nominating and Governance Committee.

Further details regarding our shareholder engagement program and actions taken by the Company in response to shareholder feedback may be found under "Executive Compensation - Compensation Discussion & Analysis - Results of Shareholder Vote on Compensation and Shareholder Engagement" beginning on page 35.

Communications with the Board



Shareholders and other interested parties may send written communications directed to the Board, a committee of the Board, the Board's Chair, a committee Chair, independent directors as a group or an individual director, by mail to the address specified in this section. The notice may specify whether the communication is directed to the entire Board, to the independent directors, or to a particular Board committee or individual director.									Enstar Group Limited Attention: Corporate Secretary P.O. Box HM 2267 Windsor Place, 3rd Floor 22 Queen Street Hamilton HM JX Bermuda

Our Corporate Secretary's office will review any communications sent to the Board and provide the Board with a summary and copies of communications that relate to the functions of the Board or a Board committee or that otherwise warrant Board attention. In addition, the Office of the Corporate Secretary may forward certain communications only to the Board's Chair, the Chair of the relevant Board committee or the individual Board member to whom a communication is directed. Concerns relating to the Company’s accounting, internal accounting controls or auditing matters will be referred directly to members of the Audit Committee. Those items that are unrelated to the duties and responsibilities of the Board or its committees may not be provided to the Board by the Office of the Corporate Secretary, including, without limitation, business solicitations, advertisements and surveys; requests for donations and sponsorships; job referral materials such as resumes; unsolicited ideas and business proposals; and material that is determined to be illegal or otherwise inappropriate.


			Enstar Group Limited / 26 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

OUR EXECUTIVE OFFICERS

Management of the Company is led by our executive officers. The following table presents information regarding our executive officers as of the date of this proxy statement.



						Dominic Silvester Chief Executive Officer Biographical Information Dominic Silvester has served as a director and the Chief Executive Officer of the Company since its formation in 2001. In 1993, Mr. Silvester began a business venture in Bermuda to provide run-off services to the insurance and reinsurance industry. In 1995, the business was assumed by Enstar Limited, which is now a subsidiary of the Company, and for which Mr. Silvester has since then served as Chief Executive Officer. Prior to co-founding the Company, Mr. Silvester served as the Chief Financial Officer of Anchor Underwriting Managers Limited from 1988 until 1993.
						Officer Since: 2001			Age: 62



						Orla Gregory President Biographical Information Orla Gregory was appointed President in March 2023. She previously served as Chief Financial Officer in from September 2021 to March 2023 and served as our Chief Operating Officer since 2016. Since joining us in 2003, Ms. Gregory has held increasingly senior roles, including Chief Integration Officer from 2015 to 2016, Executive Vice President of Mergers and Acquisitions of our subsidiary, Enstar Limited, from 2014 to 2015, Senior Vice President of Mergers and Acquisitions from 2009 to 2014, and Financial Controller from 2003 to 2009. Ms. Gregory previously served as a Financial Controller of Irish European Reinsurance Company Ltd. in Ireland, an Investment Accountant with Ernst & Young Bermuda, and as a Financial Accountant for QBE Insurance & Reinsurance (Europe) Limited.
						Officer Since: 2015			Age: 49



						Nazar Alobaidat Chief Investment Officer Biographical Information Nazar Alobaidat joined Enstar as Chief Investment Officer in 2016. He formerly served as Managing Director and CIO of AIG Property Casualty's U.S., Canada and Bermuda regions and was with AIG from 2009-2016. Prior to that, he served as Vice President within the investment banking division of Lehman Brothers and Barclays Capital, specializing in derivatives and financing transactions for corporate clients of the investment bank. He previously served in the capital markets group of Deloitte from 2001-2006. Mr. Alobaidat is a Certified Public Accountant with a master's degree from the University of Florida.
						Officer Since: 2019			Age: 45


			Enstar Group Limited / 27 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters



						Paul Brockman Chief Operating Officer and Chief Claims Officer Biographical Information Paul Brockman was appointed Chief Operating Officer in March 2023 and continues in his role as Chief Claims Officer, a position he has held since September 2020. He previously served as the President and Chief Executive Officer of Enstar (US) Inc. ("Enstar US") from July 2016 to September 2020. He served as President and Chief Operating Officer of Enstar US from November 2014 to July 2016. From October 2012 to November 2014, he served as Senior Vice President, Head of Commutations for Enstar US. Before joining Enstar US, he worked as Head of Reinsurance for Resolute Management Services UK Ltd. in its London office from April 2007 to October 2012 and, from April 2001 to April 2007, he worked as Manager of Reinsurance Cash Collection and Debt Litigation within the reinsurance asset division of Equitas Management Services Ltd in London.
						Officer Since: 2016			Age: 50



						Audrey Taranto General Counsel Biographical Information Audrey Taranto has served as General Counsel since February 2019. From June 2017 to February 2019, she served as Group Head of Legal and from to April 2012 to June 2017 as SVP, Securities Counsel. She continues to serve as the Company’s Corporate Secretary, a position she has held since 2012. Prior to 2012, she was Senior Counsel and Assistant Corporate Secretary at Cigna Corporation and an Associate in the corporate department of Drinker Biddle & Reath LLP.
						Officer Since: 2020			Age: 43



						Matthew Kirk Chief Financial Officer Biographical Information Matthew (Matt) Kirk was appointed Chief Financial Officer in March 2023. He joined Enstar in April 2020 as Group Treasurer and Head of Capital Management and he was responsible for raising and efficiently allocating capital across the Group. In addition, Mr. Kirk leads our Investor Relations function, driving all investor and rating agency communications. Previously, Mr. Kirk held executive roles at Sirius International Insurance Group, including Group Treasurer and Head of Investor Relations, and President, Managing Director of Sirius Investment Advisors. Mr. Kirk was also an Assurance and Business Advisory Manager at Arthur Andersen. Mr. Kirk holds a B.S. in Accounting from the University of Delaware and an MBA from Columbia University. He is also a Certified Public Accountant (inact).
						Officer Since: 2022			Age: 49


			Enstar Group Limited / 28 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters



						David Ni Chief Strategy Officer Biographical Information David Ni was appointed Chief Strategy Officer in May 2022. He joined Enstar and served as Executive Vice President, Mergers & Acquisitions from 2019. Prior to joining Enstar, Mr. Ni spent his career as an investment banker working in the U.S. and in Asia, and was a Managing Director at Deutsche Bank with responsibility for leading M&A in financial services. Prior to that, he was with Goldman Sachs for more than 10 years covering the financial services sector. Mr. Ni graduated with a Bachelor’s degree from Harvard.
						Officer Since: 2022			Age: 39



						Laurence Plumb Chief of Business Operations Biographical Information Laurence Plumb was appointed Chief of Business Operations in May 2022, having joined Enstar in April 2020 as Director of Operational Performance. Previously, Mr. Plumb worked in Financial Services in London for more than 13 years, focused on Financial Planning and Analysis and Capital Management at the Global Health Insurer BUPA and at RSA Insurance Group. He trained in Deloitte's Insurance and Investment Management Audit Practice and is a Fellow Chartered Accountant (FCA) of the Institute of Chartered Accountants in England and Wales (ICAEW). Mr. Plumb graduated with a Master's degree in Modern Languages from Cambridge University.
						Officer Since: 2022			Age: 39



						Seema Thaper Group Chief Risk Officer Biographical Information Seema Thaper was appointed Group Chief Risk Officer in September 2021. She joined Enstar in July 2019 as Deputy Chief Transaction Actuary and served as the Chief Transaction Actuary from January 2020 to September 2021. Prior to joining Enstar, Ms. Thaper was a Director in Deloitte's Actuarial Insurance practice leading the UK General Insurance Actuarial Advisory team. With more than 15 years of consulting experience before joining Enstar, Ms. Thaper's work has spanned across a broad cross section of the P&C Insurance market. Ms. Thaper is a Fellow of the Institute and Faculty of Actuaries.
						Officer Since: 2022			Age: 42


			Enstar Group Limited / 29 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

DIRECTOR COMPENSATION

Our Human Resources and Compensation Committee is responsible for periodically reviewing and making recommendations to our Board regarding all matters pertaining to compensation paid to directors for Board, Board leadership and committee service. The Human Resources and Compensation Committee conducts a comprehensive review of non-employee director compensation biennially. Directors who are employees of the Company receive no fees for their services as directors.

In making non-employee director compensation recommendations, the Human Resources and Compensation Committee takes various factors into consideration, including, but not limited to, the responsibilities of directors and committee members generally, the responsibilities of Board and committee chairs, and the amount of compensation paid to directors by comparable companies. The charter of the Human Resources and Compensation Committee also authorizes the Committee to engage and work with our independent compensation consultant in connection with its review and analysis of director compensation, if and when it deems appropriate. The Board reviews the recommendations of the Human Resources and Compensation Committee and determines the form and amount of director compensation.

Effective January 1, 2022, we revised the structure and amounts of our director retainer fees and removed meeting fees following a comprehensive review completed by the Human Resources and Compensation Committee during 2021.

Annual Director Compensation Program

In 2022, our director compensation program included:

▪a retainer payable quarterly for non-employee directors, and additional retainers payable quarterly for the Chairman of the Board, committee chairs and committee members; and

▪an equity retainer payable annually in the form of restricted ordinary shares with a one-year vesting period for non-employee directors and the Chairman of the Board.

Our director, Board leadership and committee retainer fees in place as of December 31, 2022 are set forth below. Committee retainer fees differ due to workload and composition of each committee and are periodically evaluated by the Human Resources and Compensation Committee.


2022 Retainer Fees(1)			Annual Amounts Payable
Non-Employee Directors(2)			$200,000
Chairman of the Board(3)			$350,000
Audit Committee Chair			$35,000
Audit Committee Member			$15,000
Human Resources and Compensation Committee Chair			$25,000
Human Resources and Compensation Committee Member			$10,000
Risk Committee Chair			$20,000
Risk Committee Member			$10,000
Investment Committee Chair			$15,000
Investment Committee Member			$10,000
Nominating and Governance Committee Chair			$15,000
Nominating and Governance Committee Member			$8,000

(1)Committee Member retainer fees are not payable to the chair of such committee or any member who is an employee of the Company.

(2)The Non-Employee Director retainer fee is payable to all non-employee directors other than the Chairman of the Board. The Non-Employee Director retainer fee is payable half in cash and half in restricted ordinary shares subject to a one-year vesting period.

(3)The Chairman of the Board retainer fee is is payable half in cash and half in restricted ordinary shares subject to a one-year vesting period.


			Enstar Group Limited / 30 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

Deferred Compensation Plan

The Amended and Restated Enstar Group Limited Deferred Compensation and Ordinary Share Plan for Non-Employee Directors (the "Deferred Compensation Plan") provides each non-employee director with the opportunity to elect (i) to defer receipt of all or a portion of his or her cash or equity compensation until retirement or termination and (ii) to receive all or a portion of his or her cash compensation for services as a director in the form of our ordinary shares instead of cash.

Non-employee directors electing to defer compensation have such compensation converted into share units payable as a lump sum distribution after the director leaves the Board. The lump sum share unit distribution is made in the form of ordinary shares, with fractional shares paid in cash. Non-employee directors electing to receive compensation in the form of ordinary shares receive whole ordinary shares (with any fractional shares payable in cash) as of the date compensation would otherwise have been payable. A director's participation in the Deferred Compensation Plan does not affect the vesting schedule of the equity portion of the retainer fees described above.

Director Compensation Table

The following table summarizes the 2022 compensation of our non-employee directors who served during the year.


Name	Fees Earned or Paid in Cash(1)(2)	Stock Awards(3)	Total
Robert Campbell	$251,250	$175,000	$426,250
B. Frederick Becker	$160,750	$100,000	$260,750
Sharon A. Beesley	$111,000	$100,000	$211,000
James Carey(4)	$114,500	$100,000	$214,500
Susan L. Cross	$129,750	$100,000	$229,750
Hans-Peter Gerhardt	$124,500	$100,000	$224,500
W. Myron Hendry	$122,250	$100,000	$222,250
Hitesh Patel	$148,750	$100,000	$248,750
Poul Winslow(5)	$125,750	$83,333	$209,083

(1)Director fees listed in this column may be deferred by directors under the Deferred Compensation Plan.

(2)Share units (rounded to the nearest whole share) acquired in lieu of the cash compensation portion of director retainer fees for 2022 under the Deferred Compensation Plan were as follows: (a) Mr. Campbell — 1,141 units; (b) Mr. Carey — 520 units; and (c) Mr. Patel — 540 units. Total share units under the Deferred Compensation Plan held by directors as of the record date are described in the footnotes to the Principal Shareholders and Management Ownership table. Mr. Gerhardt received 563 ordinary shares in lieu of fees earned in cash for 2022.

(3)This column lists the aggregate grant date fair value of Enstar restricted ordinary shares awarded to directors as part of their Board retainer and Chairman of the Board retainer, computed in accordance with FASB Accounting Standards Codification (ASC) Topic 718. The value of the restricted ordinary shares is determined based on the closing price of our ordinary shares on the grant date. For information on the valuation assumptions with respect to awards made, refer to Note 21 to our consolidated financial statements for the year ended December 31, 2022, as included in our Annual Report on Form 10-K for the year ended December 31, 2022. The amounts above reflect the grant date fair value for these awards, excluding the accounting effect of any estimate of future forfeitures, and do not necessarily correspond to the actual value that might be recognized by the directors. Restricted ordinary shares are subject to a one-year vesting period and are forfeited in their entirety if a director leaves the Board prior to the vesting date. Restricted ordinary share awards listed in this column may be deferred by directors under the Deferred Compensation Plan in the form of restricted share units, subject to the same one-year vesting period ("RSUs"). The number of restricted ordinary shares or RSUs (rounded to nearest whole share) acquired by our directors during 2022 was as follows: (a) Mr. Campbell — 667 RSUs; (b) Mr. Becker — 381 restricted ordinary shares; (c) Ms. Beesley – 381 restricted ordinary shares; (d) Mr. Carey – 381 RSUs; (e) Ms. Cross – 381 restricted ordinary shares; (f) Mr. Gerhardt — 381 restricted ordinary shares; (g) Mr. Hendry — 381 RSUs; (h) Mr. Patel — 381 RSUs; and (i) Mr. Winslow — 379 restricted ordinary shares. Fractional amounts are payable in cash at the time of vesting. Total restricted ordinary shares and RSUs held by directors as of the record date are described in the footnotes to the Principal Shareholders and Management Ownership table.

(4)Mr. Carey holds fees accrued for his service as a director solely for the benefit of Stone Point Capital, of which he is a Managing Director.

(5)Pursuant to the terms of his employment with Canada Pension Plan Investment Board ("CPP Investments") and for such time as he was employed by CPP Investments, cash fees earned by Mr. Winslow were paid directly to CPP Investments, and he waived his equity retainer fee. Mr. Winslow retired from CPP Investments effective May 2, 2022, and as of June 1, 2022, cash fees and equity retainers earned by Mr. Winslow were payable directly to him.


			Enstar Group Limited / 31 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

Executive

Compensation

Proposal 2:

Advisory Vote to Approve
Executive Compensation

WHAT AM I VOTING ON?

Shareholders are being asked to approve, on an advisory basis, the compensation of the Named Executive Officers as described in the Compensation Discussion and Analysis beginning on page 33 and the Executive Compensation Tables beginning on page 51.

The Board recommends a vote FOR the advisory vote to approve executive compensation

We hold an advisory vote on our executive compensation each year. Accordingly, we are asking our shareholders to cast an advisory vote to approve the compensation of our executive officers as disclosed in this proxy statement.

Before you vote, we urge you to read the Compensation Discussion and Analysis and the Executive Compensation Tables sections of this proxy statement for additional details on our executive compensation, including its governance, framework, components, and the compensation decisions for our executive officers for 2022.

As an advisory vote, the results of this vote will not be binding on the Board or the Company. However, the Board values the opinions of our shareholders, and will, as it did last year, carefully consider the outcome of the vote when making future decisions on the compensation of our executive officers and our executive compensation principles, policies and procedures.

We ask our shareholders to approve the compensation of our executive officers by voting "FOR" the following resolution:

"RESOLVED, that the Company’s shareholders approve, on an advisory basis, the compensation of the executive officers, as disclosed in the Company’s proxy statement for the 2023 Annual General Meeting of Shareholders pursuant to the compensation disclosure rules of the Securities and Exchange Commission, including the Compensation Discussion and Analysis, the Summary Compensation Table and the other related tables and disclosure."


			Enstar Group Limited / 32 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

COMPENSATION DISCUSSION AND ANALYSIS

Company Performance

In 2022, the Company successfully acquired $2.7 billion of incremental liabilities, including the industry’s third largest loss portfolio transfer agreement with Aspen Insurance Holdings. Our Run-off Liability Earnings of $756 million in 2022 were driven by our ability to consistently drive better outcomes through claims management. However, our investment portfolio was impacted by the combination of interest rate increases, widening credit spreads and equity market declines, which drove us to incur a net loss attributable to Enstar ordinary shareholders of $906 million for 2022, largely due to net realized and unrealized investment losses of $1.6 billion. This result created a 25.2% decrease in our book value per share and return on equity of (15.6)%. As of December 31, 2022, our book value per share was $246.20. Despite the challenging financial result, the Company delivered on many key operational initiatives and is well-positioned for 2023.

The graphs below show our performance versus the peer median in growth in book value per common share (compounded annually) during the three- and one-year periods ended December 31, 2022 and return on equity for the same time periods. Although relative performance metrics are not built into our incentive programs because of the unique nature of our business (as described in "- Peer Group" below), our Human Resources and Compensation Committee (the "Compensation Committee") monitors our performance versus our peers for background information purposes.

Management Team

During 2022, our principal executive officer, principal financial officer, and three most highly compensated executive officers were:

•Dominic Silvester - Chief Executive Officer ("CEO") and co-founder;

•Paul O'Shea - President and co-founder;

•Orla Gregory - Chief Financial Officer ("CFO");

•David Ni - Chief Strategy Officer ("CSO"); and

•Paul Brockman - Chief Claims Officer ("CCO").

On July 1, 2022, Paul O'Shea notified us of his intent to resign as President on March 1, 2023, and we entered into a letter agreement with Mr. O'Shea on July 6, 2022 (the "Letter Agreement") setting out his retirement terms. Following Mr. O'Shea's retirement and effective March 2, 2023: (i) Orla Gregory was appointed as President; (ii) Matthew Kirk, previously the Company's Treasurer, was appointed as CFO; and (iii) Paul Brockman was appointed as our Chief Operating Officer. Mr. Brockman continues to serve as our Chief Claims Officer and Mr. O'Shea remains on our Board.

Contributions of each of the executive officers in 2022 are described more fully in this Compensation Discussion and Analysis ("CD&A").


			Enstar Group Limited / 33 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

Objectives of our Executive Compensation Program

Our Compensation Committee is responsible for establishing the philosophy and objectives of our compensation program, designing and administering the various elements of our compensation program, and assessing the performance of our executive officers and the effectiveness of our compensation program.

We operate in an extremely competitive and rapidly evolving industry, and we believe that the skill, talent, judgment, and dedication of our executive officers are critical to increasing the long-term value of our company. In recent years, we have seen new entrants into the run-off business as well as increased competition in the broader market for talent. In its 2022 Global Insurance Run-Off Survey, PwC estimates that approximately $10 billion of new capital has entered the non-life run-off market in the last three years. Retaining and properly incentivizing our key executives and employees in this competitive environment is a priority for the Board and the Compensation Committee.

We therefore strive to maintain an executive compensation program that will:

▪incentivize performance consistent with clearly defined corporate objectives;

▪align our executives’ long-term interests with those of our shareholders;

▪competitively compensate our executives; and

▪retain and attract qualified executives to drive our long-term success.

We have long identified growing our book value per share and return on equity as our key corporate objectives, and we believe that long-term growth in book value and consistent returns on equity are important measures of our financial performance. Success in delivering on these measures is driven primarily by growth in our net earnings, which is in turn driven in large part by: (i) successfully pricing and completing new run-off transactions; (ii) effectively managing claims to generate run-off liability earnings; (iii) effectively managing our investments to deliver attractive risk-adjusted returns; and (iv) prudently managing our capital.

2022 Financial Metrics

For 2022, we used several financial metrics in our annual and long-term incentive compensation programs, which include: (i) Adjusted Return on Equity ("Adjusted ROE"), (ii) three-year growth in Adjusted Book Value per Share ("Adjusted BVPS"), and (iii) three-year average Adjusted ROE. Adjusted ROE and Adjusted BVPS are non-GAAP financial measures that we disclose for investors to use in evaluating the performance of our business. For a complete description of these financial measures refer to Appendix A - "Non-GAAP Financial Measures."

Roles of Executive Officers

The Compensation Committee makes compensation determinations for all of our executive officers. As part of the determination process, Mr. Silvester, our CEO, assesses our overall performance and the individual contribution of each member of the executive leadership team. On an annual basis, he reviews the prior year’s compensation and presents recommendations for salary adjustments and annual incentive awards for each executive officer, taking into consideration each executive's achievement of his or her operational performance objectives. The Compensation Committee meets in executive session without Mr. Silvester to evaluate his recommendations, review the performance of all of the executive officers, discuss CEO compensation, and make final compensation decisions.

Ms. Gregory, our President, attends portions of the meetings of our Compensation Committee to provide information relating to our financial results and plans, performance assessments of our executive officers, human resources strategies and other personnel-related data, and she supports Mr. Silvester in preparing recommendations to the Compensation Committee.


			Enstar Group Limited / 34 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

Results of Shareholder Vote on Compensation and Shareholder Engagement

We have a long-standing shareholder outreach program where we routinely interact with shareholders and two major proxy advisory firms on a number of matters, including executive compensation. We have taken, and continue to take, the feedback we receive from our shareholders and advisory firms into account in making compensation decisions and designing future compensation programs. The timing, structure, and participants of our shareholder engagement program are detailed in "Corporate Governance - Shareholder Engagement" above.

Specific shareholder comments relating to compensation practices and the Compensation Committee's responses are set forth below.



Shareholder Comment			Compensation Committee Action / Rationale
Demonstrate Enstar's shareholder responsiveness			The following summarizes feedback received and the Compensation Committee's response.
Explain rationale for use of LTI awards that are not expected to be part of an annual grant cycle			The CD&A summarizes the rationale for long-term equity incentive ("LTI") award practices, including those executives who receive LTI awards once every three years, primarily for legacy reasons, and an executive who received a retention based RSU award in 2022. We are committed to providing detailed disclosure for any future off-cycle grants.
Avoid using the same performance measure in both short and long-term awards			The Compensation Committee acknowledges concerns regarding overlapping metrics and considered this during its deliberations. For 2022, we eliminated the overlapping growth in Adjusted BVPS metric from the Annual Incentive Compensation Program (the "AIP"). We maintained an Adjusted ROE one-year metric in the AIP and an average annual Adjusted ROE three-year metric in half of our PSU awards because: (i) we manage our business, build our forecast, and measure our performance using Adjusted ROE each year and (ii) one-year Adjusted ROE is distinguishable from the PSU metric, which uses a three-year average.
Consider increasing the weighting of financial metrics within the Annual Incentive Compensation Program			The Compensation Committee acknowledges that financial metrics are an important part of annual compensation, and we give substantial weighting to Adjusted ROE in calculating executive annual incentive awards. However, our strategy often leads to volatility within a one year period that is not reflective of the success of the strategy in creating long-term value creation for shareholders. In restructuring the Annual Incentive Compensation Program for 2022, we emphasized corporate and individual components of awards using a balanced scorecard approach, which is more fully described below. The corporate and individual objectives measured on the scorecard incentivize executives to deliver change that positions Enstar for continued growth and profitability.
Include detailed disclosure of objectives that make up qualitative components of executive compensation			In the CD&A for fiscal year 2022, we include more detailed descriptions and disclosure of the weightings of specific performance objectives that make up the qualitative components of executive compensation.
Single-trigger change in control provision in CEO employment contract conflicts with investor policies and preferences			The Compensation Committee understands this concern, and has limited this provision to the Company's CEO, pursuant to a previously entered into and negotiated contract. The Compensation Committee has committed to not entering into single-triggered arrangements in future executive employment agreements.


			Enstar Group Limited / 35 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

Principal Elements of Executive Compensation and Allocation Among Elements

Compensation Elements

Our executive compensation program currently consists of three principal elements: base salaries, annual incentive compensation and LTI compensation. Executives also receive certain other benefits, including those pursuant to their employment agreements. The table below describes the principal elements of our executive compensation as well as the other components of our program, each of which is described in more detail later in this proxy statement.



Element	Description	Key Features
Base Salary	Provides the fixed portion of an executive’s compensation that reflects scope of skills, experience and performance.	▪Provides a base component of total compensation ▪Established largely based on scope of responsibilities, market conditions, and individual and Company factors
Annual Incentive Compensation	Provides "at risk" pay that reflects annual Company performance and individual performance.	▪Aligns executive and shareholder interests ▪Rewards performance consistent with financial results and corporate and individual operational performance objectives that are designed to drive the Company's annual business plan and critical business priorities
LTI Compensation	Includes (a) PSUs that "cliff vest" following a three-year performance period subject to the Company's achievement of financial performance metrics, (b) RSUs that are subject to time- and service-based vesting conditions, and (c) for our CEO, a Joint Share Ownership Plan ("JSOP") award that "cliff vests" following a five-year performance period subject to the Company's share price growth with a payout level determined by appreciation and the achievement of a financial performance metric.	▪Aligns executive and shareholder interests ▪Drives long-term performance and promotes retention ▪Heavily weighted towards performance-based awards ▪PSUs do not vest unless performance measurements are met ▪PSU vesting occurs within a range of 50-60% to 150-200% depending on the level of achievement ▪JSOP vesting requires share price hurdle to be met on the vesting date. Additionally, the value of the award will be reduced by 20% if a performance condition tied to fully diluted book value per share is not also achieved
Other Benefits and Perquisites	Reflects the local market and competitive practices such as retirement benefits, and, in the case of our Bermuda headquarters, payroll and social insurance tax contributions. Our CEO's employment agreement also provides benefits related to residing in Bermuda including allowances for housing and certain travel expenses.	▪Provides benefits consistent with certain local market practices in order to remain competitive in the marketplace for industry talent and incentivizing certain expatriates to work primarily from Bermuda ▪Promotes retention of executive leadership team
Employment Agreements	Provides certain protections for executives and their families in the event of death or long-term disability, termination, or change in control, as well as certain other benefits.	▪Provides Enstar with protections such as restrictive covenants (non-competition, non-solicitation, confidentiality, etc.) ▪Promotes retention over a multi-year term and a sense of continuity among the leadership team ▪Consistent with competitive conditions and legal requirements in Bermuda


			Enstar Group Limited / 36 / 2023 Proxy Statement			Table of Contents

Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

Compensation Allocation Among Elements

While we do not have a pre-established policy or target for the allocation of the components of our program in a given year, the Compensation Committee believes that a meaningful portion of each executive's total compensation should be "at-risk" and performance-based. Performance-based elements include our Annual Incentive Compensation Program ("AIP") awards (a "bonus award") and our JSOP and PSU LTI awards.

Our approach to allocating compensation among elements is split between: (i) long-standing executives (Dominic Silvester, Paul O'Shea and Orla Gregory) who historically have had a target bonus award of 145-150% of base salary and have been on a once-every-three-year LTI award cycle that began in 2014; and (ii) those who joined the executive team more recently who have target bonus awards of 125-150% of base salary and are eligible to receive annual LTI awards at 100% of base salary. From time to time, where a more recently appointed executive has taken on an elevated level of responsibility, or retention risk is identified, an LTI award beyond the annual LTI eligibility may be considered; these often take the form of cliff-vested RSU LTI awards. In a year where a long-standing executive is not due for an LTI award, or where a special retention RSU LTI award is made to a more recently appointed executive, the percentage of total compensation allocated to "at-risk" performance-based compensation may be lower, but the Compensation Committee believes the performance-based components remain material, particularly with respect to the long-standing executives. For example, the large once-every-three-year LTI awards granted to Mr. O'Shea and Ms. Gregory in 2020 failed to vest at the end of 2022 due to financial results below the the applicable threshold level of performance set forth in those awards.

Role of Compensation Consultants

The Compensation Committee has the authority under its charter to retain compensation consultants and outside legal counsel or other advisors and, before selecting a consultant or advisor, must consider its independence. In 2022, the Compensation Committee directly engaged McLagan, a human capital solutions division of Aon plc ("Aon") for Equity Incentive Plan share modelling and advice relating to our restructured AIP and executive officer LTI awards, including the amendment the CEO JSOP. McLagan's fees for its services during 2022 were $31,887. Aon is the parent company of subsidiaries that provide insurance brokerage-related services to our subsidiaries and affiliates unrelated to the compensation consulting services. Fees for these Aon services were $2,747,847 for 2022, and constituted a de minimis portion of Aon's 2022 revenue (less than 1%). The Compensation Committee assessed the independence of McLagan in light of applicable SEC and Nasdaq rules and reviewed responses from the consultant addressing factors related to its independence. Following this review, the Compensation Committee concluded that the firm was independent and that their advisory services did not raise any conflicts of interest.

Peer Group

In making compensatory decisions with respect to the 2022 performance year, including assessing whether we were meeting our goal of providing competitive compensation, the Compensation Committee reviewed publicly available executive officer compensation information described in the periodic filings of a group of other publicly traded companies in our industry. The Compensation Committee reviews our peer group annually, and following the most recent review, we added Essent Group Ltd. to our peer group and removed Allegheny Corporation following its acquisition by Berkshire Hathaway Inc. during the year.

The Compensation Committee generally seeks to include in our peer group companies that fall approximately within our size guidelines and include comparable aspects of our business. However, establishing a reliable peer group presents challenges for Enstar because our primary business is acquiring and operating (re)insurance companies and portfolios in run-off, whereas most in our industry focus primarily on writing new (re)insurance business. Run-off is a niche within the insurance industry, fragmented with several privately-held specialist managers, and divisions within significantly larger insurance franchises.

While pay at our peer companies is generally relevant to provide a frame of reference to the Compensation Committee in determining executive compensation, the Compensation Committee reviewed the compensation paid by these companies for informational and overall comparison purposes only. We did not compensate our executives to align with a specific benchmark or target percentile or precise position within our peer group. Instead, we sought only to be generally competitive relative to our peers with the compensation we offer our executives. Given the significant differences between us and our most similar peers relating to business, operations, and executive team


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Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

structure, we believe that formulaic benchmarking against our peer group or other companies to set 2022 compensation would not have provided meaningful guidance, although we will continue to evaluate our methodologies and views in future years.

The following companies were reviewed to provide an overall backdrop to the Compensation Committee’s decisions:

Arch Capital Group Ltd.

Essent Group Ltd.

Selective Insurance Group

Argo Group International Holdings

Hanover Insurance Group

SiriusPoint Ltd.

Assured Guaranty Ltd.

Hiscox Ltd.

White Mountains Insurance Group

AXIS Capital Holdings

Markel Corporation

W.R. Berkley

Everest Re Group Ltd.

RenaissanceRe Holdings Ltd.

The peer group selection process focused on three criteria, which was consistent with prior years: (i) industry; (ii) geography (with a significant preference for the use of Bermuda companies); and (iii) size, with reference to: (A) total shareholders’ equity within approximately 0.5 to 2.5 times of our total shareholders’ equity and (B) total assets within approximately 0.5 to 2.5 times of our total assets.

Industry. Given the lack of companies directly comparable to Enstar, we have designed our peer group around companies primarily focused on property and casualty (re)insurance, which are the companies against which we compete for talent. Where possible, we look for aspects of other companies that reflect elements similar to operations or strategies we have.

Geography. Publicly traded Bermuda companies (or publicly traded companies domiciled elsewhere with prominent Bermuda operations) are most relevant because these are the companies against which we generally compete for talent, and the Compensation Committee believes market conditions across other Bermuda-based companies are largely what drives executives’ views as to whether they are compensated competitively. We also include several companies domiciled in the United States and one in the United Kingdom in our peer group for diversification given our subsidiaries' presence in these locations.

Size. Our earnings are derived primarily from Run-Off Liability Earnings and Total Investment Return rather than revenue, making peer comparison on the basis of revenue a largely irrelevant metric for us. The Compensation Committee designed our peer group targeting companies with approximately 0.5 to 2.5 times our shareholder equity or total assets (measured using financial data available at the time of consideration), which are metrics we find most relevant for purposes of size comparison. The Compensation Committee also considers market capitalization in selecting our peer group.

Base Salaries

We set the base salaries of our executive officers based on the scope of the executives’ responsibilities and roles at Enstar, taking into account the Compensation Committee's view of the appropriate level of salary for each individual as compared to the executive's other compensation elements. The Compensation Committee considers a variety of factors in adjusting base salaries, including Company and individual performance, retention, cost of living estimates and competitive market total compensation figures for similar executive officer positions based on publicly available information. Our goal is to provide base salary amounts at levels necessary to achieve our compensation objectives of competitively compensating our executives and retaining and attracting qualified executives who are able to contribute to our long-term success. The market in which we operate is very competitive for highly qualified employees.

Mr. Silvester's base salary of $2.5 million was set in March 2021 in connection with his relocation to Bermuda and the extension of his employment and remained the same in 2022. Base salaries for Mr. O'Shea and Ms. Gregory, which were initially set in January 2020 in connection with the extension of their employment terms, also remained unchanged in 2022 at $1.5 million and $1.2 million, respectively.

The Compensation Committee increased Mr. Ni's annual base salary by 28% from $545,000 to $700,000 effective January 1, 2022 in connection with his promotion from EVP, M&A to Chief Strategy Officer. In the role of Chief Strategy Officer, Mr. Ni reports directly to the CEO and has assumed responsibility for executing Company strategic initiatives in addition to leading our M&A function. During its annual review, the Compensation Committee increased Mr. Brockman's annual base salary by 2.9% from $700,000 to $720,000, effective April 1, 2022.


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Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

Annual Incentive Compensation

The 2022-2024 Annual Incentive Compensation Program (the "AIP") provides for the grant of annual bonus compensation (a "bonus award") to our eligible employees, including our executive officers.

Changes to the Annual Incentive Compensation Program for Executive Officers for 2022

For 2022, we implemented a balanced scorecard approach for executive compensation awarded under our AIP. We adopted this approach, which places greater emphasis on selected Company and individual performance objectives, to ensure that our executives are incentivized to take actions that support long-term value creation.

The scorecard is made up of three components: a financial component, a corporate component and an individual component. The components are assigned different weightings for different executives, as described below.

2022 Bonus Award Component Weightings

Weightings among the components of each executive's potential bonus award are set forth in the table below.


Executive	Financial Component Weighting	Corporate Component Weighting	Individual Component Weighting

Dominic Silvester	45%	35%	20%
Paul O’Shea	45%	35%	20%
Orla Gregory	45%	35%	20%
Paul Brockman	20%	50%	30%
David Ni	20%	50%	30%

The Compensation Committee placed a relatively greater weighting on the financial component of the potential bonus award for Messrs. Silvester and O'Shea and Ms. Gregory, who all serve on our Board, to reflect their greater ability, given their roles and our organizational structure, to direct company actions and subsequently influence our financial results. In addition, the Compensation Committee believes that Messrs. Silvester and O'Shea and Ms. Gregory, given their shareholdings, unvested LTI awards, tenure on the executive team, and total compensation structure, should experience relatively more volatility in their bonus awards than our other executives based on our financial results.

The Compensation Committee believes overly weighting the financial component of the bonus awards could incentive executives to take actions (or refrain from taking actions) that prioritize near term performance at the expense of long-term strategy execution. The Compensation Committee therefore applies significant weighting to the corporate and individual components of bonus awards to incentivize executives to focus on process goals that support the Company's Board-approved long-term strategy, operational performance and other important initiatives that are expected to create long-term value for shareholders and further our acquisitive and opportunistic business model.

2022 Bonus Award Opportunity

For each of the financial, corporate and individual components of our scorecard, the Compensation Committee establishes threshold, target, and maximum bonus award opportunity levels for each executive officer, which are expressed as a percentage of base salary. The award opportunity levels were established consistent with the Compensation Committee's view of the appropriate level of AIP compensation for the executive's role as well as market practice, competitive conditions for similar roles, and the executive's historic level of bonus award opportunities. There were no changes to individual award opportunity levels for those individuals who were named executive officer in 2021.

The table below sets forth each executive's bonus award opportunity, expressed as a percentage of base salary. Actual payouts for performance between threshold, target and maximum are determined by straight-line interpolation.


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Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters


Executive	Reference Base Salary	Threshold (% of Base Salary)	Target (% of Base Salary)	Maximum (% of Base Salary)

Dominic Silvester	$2,500,000	100%	150%	180%
Paul O’Shea	$1,500,000	75%	150%	180%
Orla Gregory	$1,200,000	75%	145%	175%
Paul Brockman	$720,000	75%	125%	150%
David Ni	$700,000	75%	150%	175%

Financial Component

The Compensation Committee reviewed the Company's 2022 business plan with the full Board and selected Adjusted ROE as the sole financial metric for the financial component of the executives' bonus awards. Adjusted ROE replaced the prior year program's three financial metrics because it is the Company's primary annual financial planning and analysis metric. The Adjusted ROE metric improves comparability of our core operational performance across periods because it adjusts for items such as net realized and unrealized (gains) losses on fixed maturity investments and funds held-directly managed assets, which are impacted by factors such as credit spreads and interest rates, and deemed less relevant to measuring performance because our long term strategy is to hold most of our fixed maturity securities until the earlier of maturity or the time that they are used to fund any settlement of related liabilities. It also removes the impact of fair value option accounting election and the amortization of fair value adjustments, which comprises non-cash charges not reflective of the impact of our claims management strategies on our portfolios.

In setting the Adjusted ROE performance levels for 2022 (shown in the table below), the Compensation Committee established a target level aligned to the Company's business plan forecast. We believe that annual incentive financial metric performance levels should be tied to the business plan forecast for such year to ensure executives are incentivized to meet the plan targets without taking on undue risk. For 2022, the Company's business plan forecast was lower than prior years, primarily reflecting the impact of the strategic redemption and liquidation of a $2.7 billion investment portfolio during 2021. The redemption and liquidation significantly reduced our exposure to hedge fund investments, but it constrained short-term investment profits during redeployment into diversified risk assets. The 2022 business plan also reflected the short-term return implications inherent in recent adverse development cover reinsurance transactions, which constrain capital in the early years but are expected to be profitable over the medium and long term. The Compensation Committee set target Adjusted ROE levels that, although lower than prior years, would require strong performance to achieve given the factors described above.

The Company's financial results for 2022 resulted in Adjusted ROE achieving below "threshold." As a result, the overall "Financial Component" multiplier for each executive was zero, as set forth under "2022 Annual Inventive Award Building Blocks" below. The Company's Adjusted ROE performance levels and actual result for 2022 are set forth in the table below.

Financial Metric

2022 Threshold

2022 Target

2022 Maximum

2022 Actual Results

Achievement Level

Adjusted ROE(1)

6.4%

7.5%

8.6%

(1.1)%

Below Threshold

(1)Adjusted ROE is a Non-GAAP financial measure calculated by dividing adjusted operating income (loss) attributable to Enstar ordinary shareholders by adjusted opening Enstar ordinary shareholders’ equity.

Corporate Component

The corporate component aligns to our strategic focus areas and is designed to assess performance against current year objectives that are not necessarily reflected in the Company's annual financial result but are expected to lead to medium to long-term financial returns. The Compensation Committee evaluated the Company's performance against these established objectives to determine the overall "Corporate Executive Performance Rating." Within each objective set forth below, the Compensation Committee has defined specific actions that are each assigned a point value. The entire corporate component is scored based on this point value, with an 80% score corresponding to the "target" award opportunity for each executive bonus and a 60% and 100% score corresponding to the "threshold" and "maximum" award opportunities, respectively.


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Proxy Statement Summary

Corporate Governance

Executive Compensation

Audit Matters

Certain Relationships and Related Party Transactions

Other Matters

The table below sets forth the corporate objective sets that made up the corporate component of the 2022 bonus awards, the progress that was made towards achieving each objective during the year, and the score assigned for each of these objective sets for 2022 by the Compensation Committee.


Corporate Objective Set	Relative Weighting	2022 Achievements	2022 Score (%)
Return on Equity Improvement Initiatives	15%	•Developed and implemented the revised strategy for Enhanzed Re leading to unwind of Enhanzed Re joint venture and novation of Spanish life portfolio to third party acquirer, achieving return from inception on Enhanzed Re in excess of 23%. •Following evaluation of capital optimization initiatives to improve yield on mature, limited value reserve blocks, executive team determined that favorable impact of rising rates justified holding the mature reserve blocks.	76%
Group Strategy Refinements to Support Long-Term Value Creation	7%	•Conducted in depth strategy analysis, leading to several initiatives relating to capital optimization, investment allocations and the Assumed Life segment. •Developed strategies for capital returns, which led to recommendation to increase share repurchase authority.	80%
Acquisition of new liabilities accretive to long term value with projected IRR above the specified hurdle rate	7%	•Acquired $2.7 billion of incremental liabilities with projected IRR above hurdle, completing transactions with Aspen, Probitas, and Argo.	100%
Management Information Improvements	7%	•Improved financial planning and analysis models to further embed strategic decision-making, M&A, and portfolio level information through progression of multi-year initiative to develop suite of models, including completion of two key models.	80%
Investor Relations Evolution	7%	•Enhanced public disclosures and investor relations content and outreach by launching revamped 2021 and 2022 Annual Report and investor content including results podcast, which were well-received by investors.	100%
Operational Maturity & Efficiency Functional Objectives	35%	•Achieved defined operational objectives including, integration of claims relating to Aspen transaction, enhanced subsidiary governance, launch of redeveloped compliance assurance program, completion of specified systems upgrades, accounting policy change, resourcing and efficiency improvements within specified functions, and implementation of expense savings measures.	94%
Human Capital Development & Leadership	22%	•Achieved defined human capital objectives, including progressing functional leader succession planning, completing two key senior hires, adding depth of human capital resource and framework for future talent development to certain functions, and implementation of Company-wide agile performance management system and updated incentive award structure for non-executives.	78%
Weighted Average Corporate Executive Performance Rating:			87%

Individual Component

To determine each executive officer's individual performance objectives in 2022, the Compensation Committee reviewed proposals from the CEO, which were developed with each executive. The proposed objectives took into consideration the Company's goals and operational priorities for the year and fit within categories established by the Compensation Committee. Executives had multifaceted objectives within four to six categories that were individually weighted at varying levels based on the importance of each. The Compensation Committee then reviewed each proposal, made certain changes, and established the objectives and relative weightings.

The Compensation Committee reviewed interim self-appraisals to track each executive's progress towards their objectives. Following year-end, each executive submitted a final self-appraisal of his or her performance versus the goals to the Compensation Committee and the CEO. The Compensation Committee reviewed each executive officer's appraisal with the CEO before making a determination and considered his thoughts and views on overall


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