SEC Filing | James River Group Holdings

Frank N. D’Orazio

In addition to Mr. D’Orazio’s leadership of the Company as our Chief Executive Officer, the following extraordinary activities:

•

his leadership in the capital raise during spring 2021 and negotiation and execution of the loss portfolio transaction later in the year, and his work toward similar transactions that occurred in February 2022;

•

his recruitment and integration into the Company of the new chief underwriting officer, chief actuary and chief claims officer, and being instrumental in identifying and bringing on two new independent directors with extensive prior experience as executives in the insurance industry; and

•

his work in the development of an enhanced enterprise risk management system.

Sarah C. Doran

In addition to Ms. Doran’s leadership in overseeing the financial and legal functions of the Company as our Chief Financial Officer, her role in the capital raise during spring 2021 and the loss portfolio transaction later in the year, and work toward similar transactions that occurred in February 2022.

Richard J. Schmitzer

Mr. Schmitzer’s leadership of the excess and surplus segment, including the growth and profitability of the core excess and surplus lines business (excluding commercial auto).

Terence M. McCafferty

Mr. McCafferty’s leadership of the specialty admitted segment, including its significant growth and attractive combined ratio for 2021.

Daniel J. Heinlein

Mr. Heinlein’s leadership of the casualty reinsurance segment and his assistance with the segment’s loss portfolio transfer transaction in February 2022.

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UNITED STATES SECURITIES AND EXCHANGE COMMISSION

WASHINGTON, D.C. 20549

SCHEDULE 14A

(Rule 14a-101)

INFORMATION REQUIRED IN PROXY STATEMENT
SCHEDULE 14A INFORMATION

Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

Filed by the Registrant ☒

Filed by a party other than the Registrant ☐

Check the appropriate box:

☒

Preliminary proxy statement

☐

Confidential, for use of the Commission only (as permitted by Rule 14a-6(e)(2)).

☐

Definitive proxy statement

☐

Definitive additional materials

☐

Soliciting material under Rule 14a-12

James River Group Holdings, Ltd.

(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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PRELIMINARY PROXY STATEMENT — SUBJECT TO COMPLETION- DATED AUGUST 23, 2022

Wellesley House, 2nd Floor
90 Pitts Bay Road
Pembroke HM 08 Bermuda

Dear Shareholder:

You are cordially invited to attend the Annual General Meeting of Shareholders (the “Annual Meeting”) of James River Group Holdings, Ltd. (the “Company”) to be held at 8:00 a.m. local time on Tuesday, October 25, 2022 at our executive offices located at Wellesley House, 2nd Floor, 90 Pitts Bay Road, Pembroke HM 08 Bermuda.

We describe in detail the actions we expect to take at our Annual Meeting in the attached Notice of Annual General Meeting of Shareholders and proxy statement. Included with this proxy statement is a copy of our Annual Report for our year ended December 31, 2021. We encourage you to read our Annual Report. It includes information about our business as well as our consolidated audited financial statements.

Please use this opportunity to take part in our corporate affairs by voting on the business to come before the Annual Meeting. Whether or not you plan to attend our Annual Meeting, please complete, sign, date and return the accompanying proxy in the enclosed postage-paid envelope or vote electronically via the Internet or telephone. See “What options are available to me to vote my shares?” in the proxy statement for additional information. Returning the proxy or voting electronically does NOT deprive you of your right to attend the Annual Meeting or to vote your shares owned of record by you in person for the matters acted upon at the Annual Meeting.

We look forward to seeing you at the Annual Meeting.

Sincerely,

Frank N. D’Orazio

Chief Executive Officer

September [•], 2022

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NOTICE OF ANNUAL GENERAL MEETING OF SHAREHOLDERS

About the Meeting

WHEN:

WHERE:

RECORD DATE:

8:00 a.m. local time
on Tuesday, October 25, 2022

At our executive offices located
at Wellesley House, 2nd Floor,
90 Pitts Bay Road,
Pembroke HM 08 Bermuda

September 1, 2022

PROXY VOTING

It is important that your shares be represented and voted at the annual general meeting of shareholders. You can vote your shares by completing and returning the proxy card or voting instruction card sent to you. You also have the option of voting your shares on the Internet or by telephone. Voting instructions are printed on your proxy card and are included in the accompanying proxy statement. You can revoke a proxy at any time prior to its exercise at the annual general meeting of shareholders by following the instructions in the proxy statement.

VIA THE
INTERNET

VIA THE
TELEPHONE

BY MAIL

IN PERSON AT
THE MEETING

Follow the instructions on the proxy card or voting instruction form

Call the telephone number on your proxy card or voting instruction form provided by your bank, broker or other intermediary.

Sign, date, and return your proxy card in the enclosed envelope

Attend the meeting in-person

	IMPORTANT NOTICE REGARDING THE AVAILABILITY OF PROXY MATERIALS FOR THE ANNUAL GENERAL MEETING OF SHAREHOLDERS TO BE HELD ON OCTOBER 25, 2022:
	The Notice of Annual General Meeting of Shareholders, Proxy Statement and 2021 Annual Report are available at https://materials.proxyvote.com/G5005R. These documents are first being mailed to shareholders on or about September [•], 2022.

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Items of Business

ITEMS TO BE VOTED ON	BOARD’S RECOMMENDATION	MORE INFORMATION
PROPOSAL 1 To vote on a proposal to elect (i) two Class II directors for a one-year term to hold office until the 2023 annual general meeting of shareholders (assuming Proposal 2 is approved, and if not, to hold office until the 2025 annual general meeting of shareholders), (ii) one Class I director for a two-year term to hold office until the 2024 annual general meeting of shareholders, and (iii) one Class III director for a one-year term to hold office until the 2023 annual general meeting of shareholders;	FOR all nominees	41
PROPOSAL 2 To vote on a proposal to amend the Third Amended and Restated Bye-laws of the Company (the “Bye-laws”) to declassify the Board of Directors;	FOR	42
PROPOSAL 3 Re-appointment of Ernst & Young LLP, an independent registered public accounting firm, as our independent auditor to serve until the 2023 annual general meeting of shareholders and authorization of our Board of Directors, acting by the Audit Committee, to determine the independent auditor’s remuneration;	FOR	43
PROPOSAL 4 A non-binding, advisory vote to approve the 2021 compensation of our named executive officers;	FOR	45
PROPOSAL 5 To vote on a proposal to amend the Bye-laws to implement majority voting in uncontested director elections;	FOR	47
PROPOSAL 6 To vote on a proposal to amend the Bye-laws to provide a range in the size of the Board of Directors of 5 to 15 directors, with the exact number to be determined by the Board of Directors from time to time;	FOR	48
PROPOSAL 7 To vote on a proposal to amend the Bye-laws to remove supermajority voting requirements for the amendment of certain provisions of the Bye-laws and the Memorandum of Association;	FOR	49
PROPOSAL 8 To vote on a proposal to amend the Bye-laws to provide that shareholder approval of mergers and amalgamations shall require approval of a majority of the voting power attached to all issued and outstanding shares entitled to vote at a general or special meeting at which a quorum is present;	FOR	51
PROPOSAL 9 To vote on a proposal to amend the Bye-laws to remove the voting cutback and pass-through voting with respect to our subsidiaries;	FOR	52
PROPOSAL 10 To vote on a proposal to amend the Bye-laws to remove provisions pertaining to our former largest shareholders;	FOR	53
PROPOSAL 11 To vote on a proposal to amend the Bye-laws for general updates; and	FOR	54
PROPOSAL 12 To vote on a proposal to amend the James River Group Holdings, Ltd. 2014 Long-Term Incentive Plan	FOR	56

Any other business that may properly come before the annual general meeting of shareholders and any adjournments or postponements thereof.

By order of the Board of Directors,

Frank N. D’Orazio
Chief Executive Officer

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	1			BOARD OF DIRECTORS AND CORPORATE GOVERNANCE
	1			General
	1			Nominees for Election as Class II Directors, a Class I Director and a Class III Director
	3			Members of our Board of Directors Whose Terms Do Not Expire at the Annual Meeting
	5			Series A Preferred Shares Designee for Service on the Board of Directors
	6			Director Independence
	6			Board Structure
	7			Board Skills Disclosure
	7			Board Composition Disclosure
	8			Board Diversity Disclosure
	8			Risk Oversight
	8			Our Board and its Committees
	11			Annual Evaluations
	11			Compensation Committee Interlocks and Insider Participation
	11			Attendance at Annual General Meetings of Shareholders
	11			Communications with our Board of Directors
	11			Code of Conduct
	11			Prohibition on Pledging & Hedging
	11			Investor Engagement and Feedback
	14			Environmental, Social & Governance
	15			Compensation of Directors
	16			Share Ownership Guidelines
	17			EXECUTIVE OFFICERS
	19			EXECUTIVE COMPENSATION
	19			Compensation Discussion and Analysis
	28			Summary Compensation Table
	29			Grants of Plan-Based Awards
	30			Outstanding Equity Awards at Fiscal Year-End
	31			Option Exercises and Stock Vested
	31			Pension Benefits & Nonqualified Deferred Compensation
	31			Chief Executive Officer Pay Ratio
	31			Potential Payments upon Termination or Change of Control
	36			Compensation Risk Assessment
	37			EQUITY COMPENSATION PLAN INFORMATION
	38			CERTAIN RELATIONSHIPS AND RELATED TRANSACTIONS
	38			Policies and Procedures for Related Person Transactions
	38			Related Party Transactions
	39			SECURITIES OWNERSHIP OF CERTAIN BENEFICIAL OWNERS
	41			PROPOSAL NO. 1 ELECTION OF DIRECTORS
	42			PROPOSAL NO. 2 TO APPROVE AN AMENDMENT TO THE BYE-LAWS TO DECLASSIFY THE BOARD OF DIRECTORS

	43			PROPOSAL NO. 3 RE-APPOINTMENT OF ERNST & YOUNG LLP AS OUR INDEPENDENT AUDITOR
	45			PROPOSAL NO. 4 APPROVAL OF THE 2021 COMPENSATION OF OUR NAMED EXECUTIVE OFFICERS
	47			PROPOSAL NO. 5 TO APPROVE AN AMENDMENT TO THE BYE-LAWS TO IMPLEMENT MAJORITY VOTING IN UNCONTESTED DIRECTOR ELECTIONS
	48			PROPOSAL NO. 6 TO APPROVE AN AMENDMENT TO THE BYE-LAWS TO PROVIDE A RANGE IN THE SIZE OF THE BOARD OF DIRECTORS OF 5 TO 15 DIRECTORS
	49			PROPOSAL NO. 7 TO APPROVE AN AMENDMENT TO THE BYE-LAWS TO REMOVE SUPERMAJORITY VOTING REQUIREMENTS FOR THE AMENDMENT OF CERTAIN PROVISIONS OF THE BYE-LAWS AND THE MEMORANDUM OF ASSOCIATION
	51			PROPOSAL NO. 8 TO APPROVE AN AMENDMENT TO THE BYE-LAWS TO REQUIRE APPROVAL OF MERGERS AND AMALGAMATIONS BY A MAJORITY OF THE VOTING POWER ATTACHED TO ALL ISSUED AND OUTSTANDING SHARES
	52			PROPOSAL NO. 9 TO APPROVE AN AMENDMENT TO THE BYE-LAWS TO REMOVE THE VOTING CUTBACK AND PASS-THROUGH VOTING WITH RESPECT TO OUR SUBSIDIARIES
	53			PROPOSAL NO. 10 TO APPROVE AMENDMENTS TO THE BYE-LAWS TO REMOVE PROVISIONS PERTAINING TO OUR FORMER LARGEST SHAREHOLDERS
	54			PROPOSAL NO. 11 TO APPROVE AMENDMENTS TO THE BYE-LAWS FOR GENERAL UPDATES
	56			PROPOSAL NO. 12 TO APPROVE AN AMENDMENT TO THE JAMES RIVER GROUP HOLDINGS, LTD. 2014 LONG-TERM INCENTIVE PLAN
	64			OTHER MATTERS
	64			Delinquent Section 16(a) Reports
	64			Other Business at the Annual Meeting
	64			Shareholder Proposals and Director Nominations for the 2023 Annual General Meeting of Shareholders
	64			Shareholders Sharing the Same Address

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	66			FREQUENTLY ASKED QUESTIONS
	66			Where and when will the meeting take place?
	66			What proposals are to be presented at the Annual Meeting and what are the Board of Directors recommendations?
	67			Who is entitled to vote at the Annual Meeting?
	67			How many votes do I have?
	67			What is the difference between holding shares as a shareholder of record and as a beneficial owner?
	68			What if I do not vote for some of the items listed on my proxy card or voting instruction card?
	68			What options are available to me to vote my shares?
	68			How many votes must be present to hold the Annual Meeting?
	69			What is the vote required to pass each proposal to be presented at the Annual Meeting?
	69			What does it mean if I receive more than one set of proxy materials?
	69			Can I change or revoke my vote after I return my proxy card or voting instruction card?
	69			How can I attend the Annual Meeting?
	70			What is a proxy? How do I appoint a proxy and instruct that individual how to vote on my behalf?
	70			What does solicitation of proxies mean?

	70			What else will happen at the Annual Meeting?
	70			How can I access James River Group Holdings, Ltd.’s proxy materials and annual report electronically?
	70			How do I find out the voting results?
	70			Forward Looking Statements
	A-1			Appendix A
	B-1			Appendix B
	C-1			Appendix C
	D-1			Appendix D
	E-1			Appendix E
	F-1			Appendix F
	G-1			Appendix G
	H-1			Appendix H

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PROXY STATEMENT DATED September [•], 2022

FOR THE ANNUAL GENERAL MEETING OF SHAREHOLDERS to be held on October 25, 2022

We are providing these proxy materials to you in connection with our 2022 Annual General Meeting of Shareholders, which we refer to in this proxy statement as the Annual Meeting. The Annual Meeting will be held at our executive offices located at Wellesley House, 2nd Floor, 90 Pitts Bay Road, Pembroke HM 08 Bermuda on Tuesday, October 25, 2022, at 8:00 a.m. local time. This proxy statement and our 2021 Annual Report are being made available to our shareholders beginning on or about September [•], 2022. This proxy statement contains important information for you to consider when deciding how to vote on the matters brought before the Annual Meeting. Please read it carefully.

For information regarding voting your shares and other important information regarding the Annual Meeting, please see “Frequently Asked Questions” in this proxy statement.

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BOARD OF DIRECTORS AND CORPORATE GOVERNANCE

General

Our Board of Directors (the “Board of Directors” or “Board”) is currently comprised of eleven directors, with nine directors serving in office and two vacancies. The two vacancies were created upon the expiration of Christopher L. Harris’s term as a Class I director at the Company’s 2021 annual general meeting of shareholders (the “2021 Annual Meeting”) and by the retirement of Jerry R. Masters from the Board on April 26, 2022. Janet R. Cowell and Sundar S. Srinivasan, directors whose terms expire at the Annual Meeting, have each decided not to stand for re-election, thereby creating two additional vacancies upon the expiration of their terms. The Board has nominated one director to fill the vacancy created by the retirement of Mr. Masters from the Board, and, as further described below, the Nominating and Corporate Governance Committee of the Board is continuing to identify and evaluate potential additional Board members.

The existing Bye-laws provide for a classified Board of Directors, with three Classes of directors that serve staggered three-year terms. The term of Class I directors ends at our 2024 annual general meeting of shareholders, the term of Class II directors ends at the Annual Meeting, and the term of Class III directors ends at our 2023 annual general meeting of shareholders. There is one Class I director, Kirstin M. Gould, who was appointed as a director immediately following the Company’s 2021 Annual Meeting for a partial term ending at the Annual Meeting. The Board appointed Ms. Gould for a partial term, rather than for a full three-year term as a Class I director, to provide shareholders the opportunity to vote on her service as a director, instead of not having an opportunity to do so for a three-year period. The Board has nominated Ms. Gould for election at the Annual Meeting to serve as a director until the meeting held in 2024, which is the remainder of the three-year term for Class I directors. In addition, there is one Class III director, Michael T. Oakes, who the Board has nominated for election at the Annual Meeting to serve as a Class III director until the meeting in 2023, which is the remainder of the three-year term for Class III directors. The Board, with support from Mr. Oakes, determined to submit Mr. Oakes for election prior to expiration of his current term as a Class III director to give shareholders the opportunity to vote on his continued service as a director in light of the fact that Mr. Oakes received a greater number of withhold votes than votes in favor of his re-election at the Company’s 2020 annual general meeting of shareholders.

One of the items of business for the Annual Meeting is to vote on a proposal to declassify the Board so that directors are elected for one-year terms rather than three-year terms. If approved, the amendment would be effective immediately for Class II directors elected at the Annual Meeting, while directors serving in Class I or Class III will continue to serve for the remainder of the terms to which they were elected or appointed (i.e., Class III directors will serve until the Company’s 2023 annual general meeting of shareholders, and Class I directors will serve until the Company’s 2024 annual general meeting of shareholders), and at the expiration of such terms will be eligible for election for one-year terms.

Nominees for Election as Class II Directors, a Class I Director and a Class III Director

The nominees for election as Class II directors, a Class I director and a Class III director were recommended to our Board and approved for nomination by the Nominating and Corporate Governance Committee of our Board. Unless otherwise specified in the accompanying proxy, the shares voted on the proxy will be cast in favor of the election of Peter B. Migliorato and Ollie L. Sherman, Jr. as Class II directors, Kirstin M. Gould as a Class I director, and Michael T. Oakes as a Class III director. Each of the nominees has consented to being named as a nominee in this proxy statement. If, for any reason, any nominee is unable or unwilling to serve, the persons named in the proxy will use their best judgment in selecting and voting for a substitute candidate or, if Proposal 6 (pertaining to our Board’s ability to fix the size of the Board from time to time) is approved, our Board of Directors may reduce the size of our Board and eliminate the vacancies. Our Board of Directors, however, has no reason to believe that any of the nominees will be unable or unwilling to be a candidate for election at the time of the Annual Meeting.

2022 Proxy Statement1

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The following table identifies the nominees for election as Class II directors, a Class I director and a Class III director at the Annual Meeting and his or her age as of August 15, 2022.

Name

Age

Class

Position

Peter B. Migliorato

Nominee

Ollie L. Sherman, Jr.

Director

Kirstin M. Gould

Director

Michael T. Oakes

III

Director

If Proposal 2 (declassification of the Board of Directors) is approved by shareholders, the nominees for election as Class II directors will serve until the Company’s 2023 annual general meeting of shareholders and until their successors are duly elected and qualified. If Proposal 2 is not approved by shareholders, the two nominees for election as Class II directors will serve until the Company’s 2025 annual general meeting of shareholders and until their successors are duly elected and qualified. Irrespective of whether Proposal 2 is approved, the nominee for election as a Class I director will serve until the Company’s 2024 annual general meeting of shareholders and until her successor is elected and qualified, and the nominee for election as a Class III director will serve until the Company’s 2023 annual general meeting of shareholders and until his successor is elected and qualified.

Peter B. Migliorato

				Peter B. Migliorato retired in 2021 as a partner of Deloitte Consulting (“Deloitte”), where he most recently served as Lead Client Service Partner to insurance clients. Mr. Migliorato also served as the North American Insurance Consulting practice leader with Deloitte in the property & casualty, life & retirement, and employee benefits sectors. Mr. Migliorato joined Deloitte in 2001 and served in various leadership roles during his twenty-year tenure. Before joining Deloitte, Mr. Migliorato served as an equity partner at Emergence Consulting and C-Change Consulting, two start-up strategy consultancies, from 1998 to 2001 and as Senior Vice President, Marketing and Business Development at Marketing Technologies International, a data sciences firm, from 1997 to 1998. Prior to that, he led the Insurance Practice, served clients across multiple industries, and was Chief of Staff to the CEO of Gemini Consulting, a global management consulting firm, from 1985 to 1997. Mr. Migliorato serves as an advisory board member to Machine Cover, Inc., an insurance technology company, since June 2021. He served on the board of directors of State Automobile Mutual Insurance Company, the mutual holding company parent of State Auto Financial Corporation (“State Auto”) from March 2021 until State Auto was acquired by Liberty Mutual Holding Company Inc. in March 2022; and as an advisory board member to Safekeep, Inc., an insurance technology company, from June 2021 until its acquisition by CCCIS in February 2022. Mr. Migliorato received a Bachelor of Arts degree with dual majors in History and Geology from Oberlin College where he was also a member of the Phi Beta Kappa academic honor society.
	We believe Mr. Migliorato’s qualifications to serve on our Board of Directors include his extensive experience at Deloitte advising insurance companies on implementation of growth strategies, executing mergers and acquisitions and implementing technology and data platforms, his knowledge of the property and casualty insurance industry and his experience as an advisory board member to two insurance technology companies.

Ollie L. Sherman, Jr.

				Ollie L. Sherman, Jr. has served on our Board of Directors since May 2016. Mr. Sherman retired as a Managing Principal with Towers Watson in 2010. At Towers Watson, Mr. Sherman functioned as a consulting actuary and practice manager for Tower Watson’s property and casualty division for over 25 years. Prior to joining Towers Watson, Mr. Sherman was employed by the Travelers Insurance Company for ten years where he had overall responsibility for countrywide workers’ compensation pricing. Mr. Sherman graduated from the University of Virginia with a B.S. in Applied Mathematics, and he is a Fellow of the Casualty Actuarial Society.
	We believe Mr. Sherman’s qualifications to serve on our Board of Directors include his extensive experience as a consulting actuary in property and casualty insurance, as well as his knowledge of the Company gained from his service on our Board.

2James River Group Holdings, Ltd.

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Kirstin M. Gould

				Kirstin M. Gould has served on our Board of Directors since October 2021. Ms. Gould served as Executive Vice President, General Counsel and Corporate Secretary of XL Group Ltd (“XL”), a NYSE listed global insurance and reinsurance company, until XL was acquired by AXA, S.A. in 2018. Ms. Gould joined XL in 2000 and served in various leadership roles during her tenure, including leading the marketing and communications function from 2007-2015 while concurrently serving as General Counsel from September 2007. From 2005-2011, Ms. Gould chaired the Policy Committee of the Association of Bermuda Insurers and Reinsurers (ABIR), which is a trade association of international property and casualty insurers and reinsurers. Ms. Gould currently serves on the board of Pacific Life Re Global Limited where she is a member of the Risk, Audit and Remuneration Committees. She is also the founder of Harrington Advisors LLC, a consulting company focused on strategic advice including M&A, corporate governance and insurance regulatory matters. Ms. Gould began her career in private practice with the law firms Dewey Ballantine LLP in New York (1991-1995) and Clifford Chance LLP in New York and London (1996-2000). Ms. Gould received a Bachelor of Arts degree (summa cum laude) from the State University of New York at Albany and a Juris Doctor degree (cum laude) from the State University of New York at Buffalo School of Law.
	We believe Ms. Gould’s qualifications to serve on our Board of Directors include her executive leadership at an international insurance and reinsurance business, as well as her extensive experience in corporate governance, risk management, insurance regulatory matters and insurance company mergers and acquisitions.

MICHAEL T. OAKES

				Michael T. Oakes has served on our Board of Directors since December 2007. Mr. Oakes has served as the President of Conifer Group, Inc., a consulting company, since February 2011. Prior to this, Mr. Oakes served as Executive Vice President of the Company from June 2010 until his retirement in January 2011. From December 2007 through June 2010, Mr. Oakes served as our Chief Financial Officer, and from March 2008 through June 2010, he served as our Chief Executive Officer. From 2004 through 2007, he served as Chief Financial Officer of James River Group and from 1998 until 2004, Mr. Oakes was a Managing Director in the Insurance Investment Banking Group at Keefe, Bruyette & Woods, Inc., an investment banking firm based in New York. Mr. Oakes received a B.S. in Business Administration with a concentration in Accounting from the University of North Carolina at Chapel Hill and an M.B.A. from Harvard Business School.
	We believe Mr. Oakes’s qualifications to serve on our Board of Directors include his broad range of management, investment banking and capital markets experience, with a focus on financial institutions and insurance companies, as well as his background in accounting and his knowledge of the Company gained from his prior experience as an executive of the Company and service on our Board.

Members of our Board of Directors Whose Terms Do Not Expire at the Annual Meeting

The following table identifies the continuing members of our Board of Directors, their age as of August 15, 2022, the class each director serves in, and the positions each director presently holds with the Company.

Name

Age

Class

Position

J. Adam Abram

III

Non-Executive Chairman of the Board

Thomas L. Brown

Director

Frank N. D’Orazio

III

Chief Executive Officer and Director

Patricia H. Roberts

Director

2022 Proxy Statement3

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The following biographical information is furnished as to each continuing director:

J. ADAM ABRAM

				J. Adam Abram has served as Non-Executive Chairman of the Board since November 2020. He previously served as Chief Executive Officer and Executive Chairman of the Board from August 2019 through November 2020 and from September 2014 through December 2017. Mr. Abram was Non-Executive Chairman of the Board from January 2018 to August 2019 and from October 2012 through September 2014. Mr. Abram was a founder of James River Group, Inc., our principal subsidiary, and he served as the Executive Chairman, President and Chief Executive Officer of James River Group, Inc. from its inception in 2002 through 2007 and from March 2008 until October 2012. From 2002 through 2007, and from March 2008 until October 2012, Mr. Abram also periodically served in different roles at various operating units. Mr. Abram served as lead independent director of the Yadkin Financial Corporation (“Yadkin”), a bank holding company, from July 2014 until its acquisition by F. N. B. Corporation in March 2017 and, prior to that, as Chairman of the Board of VantageSouth Bancshares, Inc., a bank holding company, and its subsidiary bank, VantageSouth Bank, from November 2011 until its acquisition by Yadkin in July 2014. He also served as Chairman of Piedmont Community Bank Holdings, Inc., a bank holding company, from the time he co-founded it in 2009 until it was also acquired by Yadkin in July 2014. Mr. Abram received his B.A. from Harvard University.
	We believe Mr. Abram’s qualifications to serve on our Board of Directors include his extensive experience as an executive officer and director in the insurance industry, experience as a founder of several financial services and other companies and his detailed knowledge of the Company gained from his service as Chairman of the Board and former Chief Executive Officer of the Company.

THOMAS L. BROWN

				Thomas L. Brown has served on our Board of Directors since October 2021. Mr. Brown retired in 2019 as the Senior Vice President and Chief Financial Officer of RLI Corp. (“RLI”), a NYSE listed specialty insurer serving diverse niche property, casualty and surety markets. He previously served as Vice President and Chief Financial Officer at RLI from 2011 to 2017. Prior to that, Mr. Brown was a partner at PricewaterhouseCoopers LLP, where he served for ten years as its Central Region Financial Services Leader and led teams responsible for the banking, insurance, capital markets, real estate and investment management business sectors. Mr. Brown currently serves on the board of directors of the Chicago Shakespeare Theater and Old National Bancorp, a Nasdaq listed company, and served on the board of First Midwest Bancorp, Inc. from 2017 until its acquisition by Old National Bancorp in February 2022. In 2020, Mr. Brown joined the board of directors of Easter Seals DuPage & Fox Valley, and he previously served on the board of Easter Seals Central Illinois. From 2004 to 2017, Mr. Brown served on the board of trustees of Illinois Wesleyan University. Mr. Brown received a Bachelor of Science degree in Accounting from Illinois Wesleyan University in 1979. He is a certified public accountant.
	We believe Mr. Brown’s qualifications to serve on our Board of Directors include his management experience at RLI, his knowledge of the property and casualty insurance industry, his financial and accounting expertise and his experience as a public company board member.

4James River Group Holdings, Ltd.

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FRANK N. D’ORAZIO

				Frank N. D’Orazio has served as our Chief Executive Officer and a director since November 2020. Mr. D’Orazio formerly served as Corporate Chief Operating Officer and Chief of Staff of Allied World Assurance Company Holdings, Ltd. (“Allied World”), a global provider of property, casualty and specialty insurance and reinsurance, from March 2019 through January 2020. Prior to that, Mr. D’Orazio served as President, Underwriting and Global Risk of Allied World from December 2014 through February 2019. From September 2009 to December 2014, Mr. D’Orazio served as the President — Bermuda and International Insurance of Allied World Ltd. From June 2003, when Mr. D’Orazio joined Allied World, through September 2009, Mr. D’Orazio held leadership roles with increasing responsibility in the company’s general casualty business and in underwriting. Before joining Allied World, Mr. D’Orazio worked for the retail insurance market arm of Munich-American Re-Insurance from August 1994 to May 2003, where he held a succession of underwriting and management positions. Prior to that Mr. D’Orazio held various underwriting positions in the excess casualty division of the Chubb Group of Insurance Companies from June 1990 to July 1994. Mr. D’Orazio received a B.A. from Fairfield University.
	We believe Mr. D’Orazio’s qualifications to serve on our Board of Directors include his extensive experience as an executive officer in the insurance industry and significant insurance and underwriting knowledge.

PATRICIA H. ROBERTS

				Patricia H. Roberts has served on our Board of Directors since July 2019. She retired in 2012 from her dual position as President and Chairman of General Star Management Company and President and Chairman of Genesis Management and Insurance Services Corporation, two wholly-owned subsidiaries of General Reinsurance Corporation (“GenRe”). Ms. Roberts began working at GenRe in 1977 and held positions with increasing levels of responsibility. Ms. Roberts served on the Navigators Group Inc. (“Navigators”) board from 2014 until 2019 when Navigators was sold to Hartford Financial Services Group. Ms. Roberts holds a Bachelor of Science degree in Business Administration from George Mason University and received her CPCU (Chartered Property Casualty Underwriter) designation in 1985.
	We believe Ms. Roberts’s qualifications to serve on our Board of Directors include her management experience at GenRe, her knowledge of the insurance and reinsurance industry, her operational and strategic expertise and her experience as a public company board member.

There are no family relationships among any of our directors or executive officers.

Series A Preferred Shares Designee for Service on the Board of Directors

In connection with the issuance and sale of 150,000 Series A Perpetual Cumulative Convertible Preferred Shares, par value $0.00125 per share (the “Series A Preferred Shares”), to GPC Partners Investments (Thames) LP (“GPC Thames”), which was completed on March 1, 2022, GPC Thames received the right to designate one individual (the “Series A Designee”) for nomination to our Board of Directors. GPC Thames has designated Matthew B. Botein, the co-founder and Managing Partner of Gallatin Point Capital LLC, an affiliate of GPC Thames, for nomination as the Series A Designee, and, accordingly, the Board approved the appointment of Mr. Botein to serve as a Class I director with a term expiring at the Company’s 2024 annual general meeting of shareholders, effective following receipt of any necessary regulatory approvals. Until applicable regulatory approvals are obtained, Mr. Botein has board observer status.

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Matthew B. Botein

				Matthew B. Botein is a co-founder of Gallatin Point Capital LLC (“Gallatin Point”), a private investment firm founded in 2017, and serves as the Managing Partner of Gallatin Point. Prior to founding Gallatin Point, Mr. Botein served as co-head and Chief Investment Officer for Alternatives of BlackRock Alternative Investors (“BAI”) from 2009 through 2017 and as an advisor to BAI from 2017 through 2020. Prior to joining BAI, Mr. Botein served as a Managing Director and member of the Management Committee at Highfields Capital Management, a Boston-based private investment partnership. He also served as a member of the private equity departments at The Blackstone Group and Lazard Frères & Co. LLC. Mr. Botein currently serves on the board of directors of Hunt Capital Holdings, Amber Infrastructure Group Holdings Limited, Fortuna Holdings Limited (parent of Lloyd’s insurer Canopius), Bowhead Insurance Holdings LP, Tower Hill Risk Management, LLC, and Northeast Bancorp (Nasdaq: NBN). Mr. Botein previously served on the board of directors of PennyMac Financial Services (NYSE: PFSI), Aspen Insurance Holdings (NYSE: AHL), CoreLogic Inc. (NYSE: CLGX), First American Corporation (NYSE: FAF), PennyMac Mortgage Investment Trust (NYSE: PMT) and numerous private companies. He also serves on the Board of Trustees of Beth Israel Deaconess Medical Center, the CareGroup/CJP Board of Managers and Boston Medical Center. Mr. Botein received a Bachelor of Arts degree (magna cum laude) from Harvard College and a M.B.A degree (with high distinction) from Harvard Business School, where he was awarded Baker and Loeb scholarships.
	For additional information regarding the issuance and sale of the Series A Preferred Shares to GPC Thames, including its right to designate a director for nomination, see “Certain Relationships and Related Transactions-Related Party Transactions”.

Director Independence

Our Board has reviewed the independence of our directors and nominees using the Nasdaq Stock Market independence standards. Based on this review, we have determined that Messrs. Brown, Migliorato, Oakes, Sherman, and Srinivasan and Ms. Cowell, Ms. Gould and Ms. Roberts are independent.

Board Structure

Mr. Abram has served as our Non-Executive Chairman since November 2020. He previously served as Chairman and Chief Executive Officer from August 2019 to November 2020 and also served in such roles from 2014 through 2017. Mr. Abram served as our Non-Executive Chairman of the Board from the time of his initial retirement in January 2018 through July 2019. The Board believes that Mr. Abram’s continued service as Chairman is appropriate because of his familiarity with the Company’s business and strategy and significant experience in the property and casualty insurance industry, based upon being the founder of the Company and other companies in the industry.

Our independent directors bring experience and expertise from outside the Company and the property and casualty insurance industry, but our Board believes that Mr. Abram, based on his vast experience and knowledge of the Company, remains in the best position to identify areas of focus for the Board and to set the Board’s agenda.

Mr. Sherman was appointed as our lead independent director following the retirement of Mr. Masters from the Board on April 26, 2022. In such capacity, Mr. Sherman will lead executive sessions of the Board of Directors and communicate with our Chief Executive Officer between meetings to discuss strategy and other matters that may require the attention of the Board of Directors.

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Board Skills Disclosure

The following table sets forth certain skills that our continuing directors and our nominee have, which we believe benefits the Board.

J. Adam
Abram

Thomas L.
Brown

Frank N.
D’Orazio

Kirstin M.
Gould

Peter B.
Migliorato

Michael T.
Oakes

Patricia H.
Roberts

Ollie L.
Sherman, Jr.

Number
of
Directors/
Nominees
with Skill

Executive Leadership

✓

6/8

Insurance Industry Expertise

✓

8/8

Risk Management

✓

7/8

Corporate Governance

✓

8/8

Business Operations

✓

8/8

Finance / Capital Management

✓

5/8

Investments

✓

3/8

Mergers and Acquisitions

✓

6/8

Information Technology / Cyber Security

✓

3/8

Legal and Regulatory

✓

1/8

Board Composition Disclosure

The following charts display the tenure, age and diversity of our directors following the Annual Meeting (assuming the election or re-election of all nominees):

[MISSING IMAGE: tm2221375d2-pc_directpn.jpg]

[MISSING IMAGE: tm2221375d2-pc_diverpn.jpg]

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Board Diversity Disclosure

The table below provides certain highlights of the composition of our Board members as of August 15, 2022. Each of the categories listed in the below table has the meaning as it is used in Nasdaq Rule 5605(f).

	Board Diversity Matrix (as of August 15, 2022)
	Total Number of Directors				9

	Female		Male		Non-Binary		Did Not Disclose Gender
Part I: Gender Identity
Directors		3		6		—		—
Part II: Demographic Background
African American or Black		—		1		—		—
Alaskan Native or Native American		—		—		—		—
Asian		—		1		—		—
Hispanic or Latinx		—		—		—		—
Native Hawaiian or Pacific Islander		—		—		—		—
White		3		4		—		—
Two or More Races or Ethnicities		—		—		—		—
LGBTQ+	—
Did Not Disclose Demographic Background	—

Risk Oversight

The Company’s management, including and under the supervision of our Chief Executive Officer, has the primary responsibility for managing risks of the Company, subject to Board oversight. The Board has delegated certain of its risk oversight responsibilities to various Board committees. Specifically, the Board has assigned oversight of the risks associated with the Company’s investment portfolio to the Investment Committee and of the risks associated with the Company’s compensation policies and practices to the Compensation Committee. The Board has delegated to the Audit Committee the responsibility for oversight of the Company’s financial risks, financial controls, internal audit and potential conflicts of interest and receives regular internal audit updates from our Chief Financial Officer and head of internal audit. Finally, our Board of Directors reviews strategic and operational risk in the context of reports from our senior management team, receives reports regarding activities of our Board committees at each regular meeting, and evaluates the risks inherent in significant transactions.

Our Board and its Committees

The Company’s Bye-laws prohibit meetings via telephone or video conferences with a director participant in the United States. This restriction proved difficult for us in 2021 due to the ongoing coronavirus pandemic (“COVID-19”). As a result of COVID-19, each of the Board and its committees were unable to hold any in-person meetings during 2021. To compensate for this difficulty, our Board and its committees held informational videoconferences on a regular basis during 2021, with actions requiring approval taken by written consent after extensive discussion in the informational sessions.

During 2021, our Board of Directors did not hold any in-person meetings, but held informational videoconferences five times. Additionally, our directors attended at least 75% of the aggregate number of informational videoconferences of our Board of Directors and committees that he or she served on during 2021, except for Mr. Harris, who did not stand for re-election at our 2021 Annual Meeting.

Our Board of Directors has established four standing committees to assist it in carrying out its responsibilities: the Audit Committee, the Compensation Committee, the Nominating and Corporate Governance Committee and the Investment Committee. Each of the Audit Committee, the Compensation Committee, the Nominating and Corporate Governance Committee and the Investment Committee operates under its own written charter. The charters of the Audit Committee, the Compensation Committee, and the Nominating and Corporate Governance Committee comply with the applicable rules and regulations of the Securities and Exchange Commission (the “SEC”) and the Nasdaq Stock Market. Copies of the

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charters of our standing committees are available on our website at http://www.JRGH.net. The membership of each committee and the function of each of the committees are described below.

AUDIT COMMITTEE

Thomas L. Brown (Chair)

Janet R. Cowell

Ollie L. Sherman, Jr.

Our Audit Committee consists of Messrs. Brown (Chairman) and Sherman and Ms. Cowell. During 2021, our Audit Committee did not hold any in-person meetings due to COVID-19, but held informational videoconferences four times.

Our Board has determined that all of the members of the Audit Committee are independent as defined under the rules of the Nasdaq Stock Market and the independence requirements contemplated by Rule 10A-3 under the Securities Exchange Act of 1934, as amended (the “Exchange Act”). Additionally, each of the members of our Audit Committee has been identified by our Board of Directors as an “audit committee financial expert” (“AC Financial Expert”) as that term is defined in Item 407(d)(5) of Regulation S-K. Mr. Brown acquired the skills necessary to qualify as an AC Financial Expert through his experience as Chief Financial Officer of RLI, his accounting and auditing experience while at PricewaterhouseCoopers LLP and status as a Certified Public Accountant. Mr. Sherman acquired the skills necessary to qualify as an AC Financial Expert through his experience at Towers Watson as a consulting actuary and manager for the company’s property and casualty insurance practice, where his responsibilities included the review of property and casualty insurance financial data in connection with the issuance of actuarial opinions for use in connection with financial statements and other financial analysis. Ms. Cowell acquired the skills necessary to qualify as an AC Financial Expert through her experience as the State Treasurer of North Carolina, where she oversaw the finances of the State as well as a significant number of local governments, including review and submission of their audited financial statements, and her M.B.A. from the Wharton School of Business and status as a level 1 CFA.

The Audit Committee assists our Board of Directors in fulfilling its oversight responsibilities relating to:

•

the integrity of our financial statements and our financial reporting process;

•

internal and external auditing and the independent registered public accounting firm’s qualifications and independence;

•

the performance of an internal audit function and our independent registered public accounting firm;

•

the integrity of our systems of internal accounting and financial controls; and

•

our compliance with legal and regulatory requirements.

In so doing, the Audit Committee is responsible for maintaining free and open communication between the committee, the independent registered public accounting firm and our management. In this role, the Audit Committee is empowered to investigate any matter brought to its attention with full access to all books, records, facilities and personnel of our Company and has the power to retain outside counsel or other experts for this purpose.

The Audit Committee has direct responsibility for the appointment, compensation, retention and oversight of our independent registered public accounting firm. The Audit Committee engages in an annual evaluation of the independent public accounting firm’s insurance industry qualifications and expertise, assesses the firm’s quality of service, the firm’s sufficiency of resources, the quality, timeliness and practicality of communication and interaction with the firm, the adequacy of information provided on accounting issues, auditing issues and regulatory developments affecting the property and casualty insurance industry, the firm’s ability to meet deadlines and respond quickly, the firm’s timeliness and accuracy of all services presented to the Audit Committee for pre-approval and review, management’s feedback, the lead partner’s performance, the comprehensiveness of evaluations of our internal control structure, and the firm’s independence, candor, objectivity and professional skepticism. The Audit Committee also considers the advisability and potential impact of selecting a different independent public accounting firm.

The Audit Committee recognizes the importance of maintaining independence of the Company’s independent auditors, both in fact and in appearance. On at least an annual basis, the Audit Committee receives and reviews written disclosures and a letter from our independent public accounting firm required by applicable requirements of the Public Company Accounting Oversight Board (“PCAOB”) regarding the firm’s communications with the Audit Committee concerning independence, and discusses with the firm the firm’s independence from the Company and management. These discussions include, among other things, a review of the nature of, and fees paid to the firm for, non-audit services and the compatibility of such services with maintaining the firm’s independence.

The Audit Committee meets with the independent registered public accounting firm and the Company’s internal audit group independently without the presence of management at least quarterly.

The Audit Committee is responsible for approving all transactions with related persons. On an annual basis, the Audit Committee reviews and approves all director and executive officer related party transactions that the Company is a party to, and on a quarterly basis receives a summary of such transactions as prepared by management. To the extent any new transactions may arise during the course of the year, management discusses such transactions with the Audit Committee. A further description of the Audit Committee’s role in reviewing related party transactions is set forth in this proxy statement under “Certain Relationships and Related Transactions.”

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COMPENSATION COMMITTEE

Patricia H. Roberts (Chair)

Ollie L. Sherman, Jr.

Sundar S. Srinivasan

Our Compensation Committee consists of Ms. Roberts (Chairperson) and Messrs. Sherman and Srinivasan. During 2021, the Compensation Committee did not hold any in-person meetings due to COVID-19, but held informational videoconferences four times.

Our Board of Directors has determined that the current members of our Compensation Committee are independent under applicable rules and regulations of the Nasdaq Stock Market.

The Compensation Committee assists our Board of Directors with reviewing the performance of our management in achieving corporate goals and objectives and assuring that our executives are compensated effectively in a manner consistent with our strategy, competitive practice and the requirements of the appropriate regulatory bodies. Toward that end, the Compensation Committee, among other responsibilities, makes recommendations to our Board of Directors regarding director and executive officer compensation, equity-based compensation plans and executive benefit plans. In determining compensation recommendations to the Board of Directors, the Compensation Committee consults with our Chief Executive Officer. The Compensation Committee also administers the Company’s incentive plans.

The Compensation Committee has authority to retain compensation consultants and fix any such consultant’s fees and other retention terms and may obtain advice and assistance from internal or external legal, accounting and other advisors as it deems necessary to fulfill its duties and responsibilities. In 2022, the Compensation Committee approved the retention of Mercer (US), Inc., an independent compensation consultant, to assist with the Company’s executive officer compensation plans and programs. For information regarding the scope of Mercer’s work, please see “Compensation Discussion and Analysis — 2022 Compensation Developments.”

NOMINATING AND CORPORATE GOVERNANCE COMMITTEE

Ollie L. Sherman, Jr. (Chair)

Kirstin M. Gould

Patricia H. Roberts

Our Nominating and Corporate Governance Committee consists of Mr. Sherman (Chairman) and Ms. Roberts and Ms. Gould. During 2021, the Nominating and Corporate Governance Committee did not hold any in-person meetings due to COVID-19, but held informational videoconferences three times.

Our Board of Directors has determined that our current members of the Nominating and Corporate Governance Committee are independent under applicable rules and regulations of the Nasdaq Stock Market. Among other responsibilities, the Nominating and Corporate Governance Committee identifies individuals qualified to become board members, recommends to the Board of Directors the director nominees for the next annual general meeting of shareholders and recommends to the Board of Directors individuals from time to time to fill vacancies on the Board of Directors.

The Nominating and Corporate Governance Committee determines the qualifications, qualities, skills and other expertise required to be a director and develops and recommends such criteria to the Board of Directors when commencing a director search (the “Director Criteria”). In evaluating a candidate for director, the committee may consider, in addition to the Director Criteria and such other criteria as the committee considers appropriate under the circumstances, whether a candidate possesses the integrity, judgment, knowledge, experience, skills, expertise, and viewpoints that are likely to enhance the Board’s ability to manage and direct the affairs and business of the Company, including, when applicable, to enhance the ability of committees of the Board to fulfill their duties. The committee may take into account the satisfaction of any independence requirements imposed by law or regulation and a candidate’s diversity. The committee has authority to retain and terminate any search firm to be used to identify director candidates and to approve the search firm’s fees and other retention terms and may obtain advice and assistance from internal or external legal, accounting and other advisors as it deems necessary to fulfill its duties and responsibilities. The committee also retained a search firm to assist the committee in its board nominee search, and the search firm identified Mr. Migliorato as a potential nominee as a director. The search firm continues to provide assistance to the committee in its ongoing search for additional nominees.

The Nominating and Corporate Governance Committee may consider candidates recommended by any of the Company’s shareholders. In considering any such candidate, the committee may use the Director Criteria and such other criteria as the committee considers appropriate under the circumstance to evaluate any such candidate. For details on how shareholders may submit nominations for directors, see “Other Matters.”

INVESTMENT COMMITTEE

Sundar S. Srinivasan (Chair)

J. Adam Abram

Michael T. Oakes

Janet R. Cowell

Our Investment Committee consists of Messrs. Srinivasan (Chairman), Abram and Oakes and Ms. Cowell. During 2021, the Investment Committee did not hold any in-person meetings due to COVID-19, but held informational videoconferences four times. The Investment Committee oversees the implementation of our overall investment policy.

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Annual Evaluations

On an annual basis each of the members of the Board and each of our committees completes a self-assessment questionnaire to determine whether the Board and each committee is functioning effectively. The questionnaires invite written comments on all aspects of the Board and each committee’s process, and are completed on an anonymous basis to encourage candor. The results are then summarized by outside counsel and reviewed at a subsequent Board meeting.

Compensation Committee Interlocks and Insider Participation

During 2021, prior to the Company’s 2021 Annual Meeting, our Compensation Committee consisted of Mr. Christopher L. Harris (Chairman), Mr. Masters and Ms. Roberts, and, after the Company’s 2021 Annual Meeting, our Compensation Committee consisted of Ms. Roberts (Chairperson), Mr. Sherman, Mr. Srinivasan, and prior to his retirement from the Board on April 26, 2022, Mr. Masters. None of our executive officers currently serves, or in the past year has served, as a member of the board of directors or compensation committee of any entity that has one or more executive officers serving on our Board of Directors or Compensation Committee.

Attendance at Annual General Meetings of Shareholders

We encourage each member of our Board of Directors to attend the annual general meeting of shareholders. In 2021, only two of our directors were able to attend our annual general meeting due to COVID-19 travel and other restrictions. We are unable to hold our annual general meeting by videoconference due to restrictions in the Bye-laws regarding participation by shareholders from the United States.

Communications with our Board of Directors

Any shareholder that desires to communicate directly with our Board of Directors, or any committee thereof, or one or more individual directors may do so by addressing the communication to our Secretary at James River Group Holdings, Ltd., Conyers Corporate Services (Bermuda) Limited, Clarendon House, P.O. Box HM 1022, Hamilton HM DX, Bermuda or InvestorRelations@jrgh.net, in either case with a request to forward the communication to the intended recipient. The outside of the envelope or subject line of the email, as applicable, should be clearly marked “Director Communication.” All such correspondence will be forwarded to the relevant director or group of directors, except for items unrelated to the functions of the Board, including business solicitations or advertisements.

Code of Conduct

We have a Code of Conduct (the “Code of Conduct”) applicable to our directors, officers and employees that complies with the requirements of applicable rules and regulations of the SEC and the Nasdaq Stock Market. This code is designed to deter wrongdoing and to promote:

•

honest and ethical conduct, including the ethical handling of avoiding actual or apparent conflicts of interest between personal and professional responsibilities to the Company;

•

full, fair, accurate, timely and understandable disclosure in reports and documents that we file with the SEC and in other public communications made by us, as well as communications with insurance and other regulators;

•

compliance with applicable governmental laws, rules and regulations;

•

prompt reporting of violations of the Code of Conduct to the Chairman of our Audit Committee; and

•

accountability for adherence to the Code of Conduct.

Our Code of Conduct is available on the Investor Relations portion of our website.

Prohibition on Pledging & Hedging

Our insider trading policy prohibits our directors, officers and employees from engaging in any pledging, hedging or monetization transactions or similar arrangements with respect to our securities. Such parties are also prohibited from engaging in any short sales, utilizing a margin account with respect to buying or selling our securities, or trading in exchange-traded options or other derivative securities.

Investor Engagement and Feedback

We are committed to effective corporate governance that is informed by our shareholders, promotes the long-term interests of our shareholders, and strengthens Board and management accountability. We have a robust shareholder outreach program that involves members of the Board of Directors, executive management and Investor Relations.

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The benefits of regular engagement include:

•

Keeping the Board and management accountable for addressing shareholder concerns;

•

Gaining and maintaining shareholder trust through visibility and transparency; and

•

Providing the Board and management with visibility into emerging issues that are important to our shareholders.

Types of Regular Engagement and Topics Covered

We engage with our shareholders through different methods. These include, among others, earnings conference calls, investor conferences, individual and group investor conference calls and conference participation, outreach, and calls and meetings with investor corporate governance departments. Topics covered through our different forms of engagement include, among others:

•

Strategic and financial goals and performance, business initiatives;

•

Executive compensation;

•

Regulatory and rating agency considerations;

•

Leadership structure;

•

Board composition, including qualification, skills, background of Board members; and

•

Board structure, including its classified structure and supermajority voting requirements.

Our 2021-2022 shareholder outreach initiative included communication with over 200 existing and potential shareholders. Additionally, shareholders and other interested parties may communicate with members of the Board of Directors, executive management and Investor Relations through InvestorRelations@jrgh.net.

Focused Engagement Prior to our 2022 Annual General Meeting

Following our 2021 Annual Meeting, and prior to the filing of this proxy statement, we reached out to 26 of our largest shareholders representing approximately 84% of our shares outstanding, assuming conversion of the Series A Preferred Shares to common shares, requesting to discuss corporate governance, executive compensation, board refreshment and other ESG matters. Participants on most calls included the Chief Financial Officer and the Senior Vice President of Investor Relations, as well as a relatively new Board member, who is a member of the Nominating and Corporate Governance Committee. We received feedback from approximately 52% of holders of our shares outstanding, assuming conversion of the Series A Preferred shares to common shares. In these meetings, we were particularly mindful of understanding shareholders’ views with respect to our Board and committee structure, executive compensation program and practices and Board refreshment. Below is a summary of the feedback received from shareholders on those topics and the changes we have made or proposed in response.

					What We Heard				What We Did
	Executive Compensation				• Adopt quantifiable based executive compensation targets and a benchmarking group.				• The Company, with the Compensation Committee’s approval, retained a compensation consultant (Mercer) to assist the Compensation Committee in evaluating the compensation of the Company’s senior executive officers. Mercer assisted the Compensation Committee in developing a peer group to assess the design of our executive compensation program and to compare executive pay levels. The Compensation Committee used the peer group information in the development of variable cash bonuses under a new short-term incentive plan and variable equity compensation under a new long-term incentive plan. In July 2022, the Board, upon the recommendation of the Committee, approved these plans. Please see “Executive Compensation — Compensation Discussion and Analysis — 2022 Compensation Developments” for further detail. • Additionally, the Board, at the recommendation of the Compensation Committee, adopted share ownership guidelines to more closely align the financial interests of the Company’s directors and executive and other senior officers with those of the Company’s shareholders. Please see “Executive Compensation — Compensation Discussion and Analysis — Share Ownership Guidelines” for further detail.

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	What We Heard	What We Did
Corporate Governance	• Some investors disfavor a classified board structure, while others found it appropriate for a company of our size and history	• The Board determined to include Proposal 2 in this proxy statement, a proposal to amend the Company’s Bye-laws to declassify the Board of Directors. If adopted by shareholders, it would eliminate the classified structure of the Board by the 2024 annual general meeting of shareholders.
	• Encouraged enhancements for shareholder rights	• The Board determined to include Proposal 5 in this proxy statement, a proposal to amend the Company’s Bye-laws to implement majority voting in uncontested director elections. • The Board determined to include Proposal 7 in in this proxy statement, a proposal to amend the Company’s Bye-laws to remove supermajority voting requirements for the amendment of certain provisions of the Bye-laws and the Memorandum of Association. • The Board determined to include Proposal 8 in this proxy statement, a proposal to amend the Company’s Bye-laws to require approval of mergers and amalgamations by a majority of the voting power attached to all issued and outstanding shares entitled to vote at the applicable meeting.
	• Preference for independent Chairperson of Nominating and Corporate Governance Committee	• The Board named Ollie L. Sherman, Jr. as its Chairperson of the Nominating and Corporate Governance Committee.
ESG	• Increase disclosures regarding ESG	• Included a section on environmental, social and governance topics in this proxy statement, which we expect to enhance over time. Please see “Board of Directors and Corporate Governance — Environmental, Social and Governance” for further details.
	• Investors expressed appreciation for the Board’s refreshment efforts	• We have continued to demonstrate our commitment to adding independent directors to our Board through the nomination of Mr. Migliorato for election as a new independent director, and expect to add additional independent directors to our Board in the future. • Including the nomination of Mr. Migliorato and the two independent directors who have joined the Board over the last year (Thomas L. Brown and Kirstin M. Gould), following the Annual Meeting 37.5% of the Board will consist of independent directors added in the last year. In addition, upon regulatory approval of Mr. Botein’s appointment to the Board, following the Annual Meeting 44% of the Board will consist of independent directors added in the last year.

In addition to responding to the feedback collected through investor conversations summarized above, we are proposing to implement changes to the Company’s 2014 Long Term Incentive Plan (the “2014 LTIP”) that our Board believes are consistent with the interests of shareholders and sound corporate governance practices. The Board determined to include Proposal 12 in this proxy statement, a proposed amendment to the 2014 LTIP, that, in addition to making additional common shares available for issuance of the plan, includes the following express modifications: (i) prohibits shares that are withheld for payment of taxes upon vesting of any award from being available for future award grants; (ii) implements a minimum vesting period for service based awards and a minimum performance period for performance based awards; (iii) prohibits the payment of dividends or dividend equivalents on awards until the underlying shares have become vested; and (iv) prohibits the transfer of awards except in the event of death or transferred for no consideration to a family member or for charitable purposes.

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Environmental, Social & Governance

We are committed to fostering a sustainable business that supports the well-being of our employees, customers and communities. We strive to put our corporate values into action every day, including by providing engaging and rewarding work for our employees and always demonstrating integrity in our actions.

Ethics

We are committed to conducting our business in compliance with the law and the highest ethical standards. The Company has adopted a Corporate Governance Manual that includes a series of policies designed to ensure our directors, officers and employees act in an ethical and legally compliant manner in the course of their service to the Company. The policies contained in the Corporate Governance Manual include, among others, our Code of Conduct, Policy on Insider Trading and Tipping, Whistleblower Policy, Conflict of Interest Policy, and Related Party Transactions Policy & Procedures. All directors, officers, and employees are required to review and sign an acknowledgement of the Corporate Governance Manual on an annual basis.

Our Employees

We strive to make James River a great place to work and a place where everyone is treated with dignity and fairness, respecting and recognizing each employee as an individual. We know our success as a company is founded on the talents, skills and efforts of our employees. We believe our culture enables us to attract and retain exceptional talent.

Diversity, Equity and Inclusion

Our strength and success derive from our diversity, and we believe we are at our best when we embrace diverse views and perspectives. Equality in opportunity, career development, compensation and respect for all individuals are fundamental human rights that are at the forefront of our culture and promoted within our workplace.

Our Board is committed to diversity within its structure, as well as emphasizing its importance in our senior executive leadership team. We believe that diversity in gender, age, ethnicity and skill set allows for dynamic and evolving perspectives in governance, strategy, corporate responsibility, human rights and risk management. We have three highly respected women with proven leadership experience as members of our Board, as well as two male members of our Board who are underrepresented minorities.

Within our Company, our Diversity, Equity and Inclusion (DEI) efforts are ultimately overseen by our Chief Executive Officer and our Chief Human Resources Officer but are developed and run on a day-to-day basis by our DEI Committee. This committee is both diverse and made up of employees from all segments, levels and office locations. Over the last year, our DEI Committee made significant progress in bringing additional awareness and focus to DEI topics throughout the Company, launching our first Listening Circle to gather feedback from employees and implementing a robust training program including sessions on DEI, Sensitivity & Racism, Unconscious Bias, Microaggressions in the Workplace, and Cultural Competency & Humility. We expect to continue to hold these sessions on a quarterly basis.

Workforce Diversity

As of December 31, 2021, we had 638 employees located in the United States and Bermuda, all classified as full-time. Of that population, 58% identified as female and 42% identified as male. Among the 98% of our employees who chose to disclose their race and ethnicity, approximately 14% identified as Black or African American, 3% as Hispanic or Latino, 6% as Asian, 2% as two or more races, less than 1% as Native Hawaiian or other Pacific Islander, and less than 1% as American Indian or Alaska Native.

Our hiring practices are designed to meet business hiring needs as well as maintain a high bar for talent. In an effort to promote diversity in our hiring practices and in the workforce broadly, we have a number of recruiting partnerships including those focused on bringing former military members into the corporate workforce; an internship program for diverse students interested in careers in the insurance industry; and a work-study program for high school students providing access to professional environments that typically are underrepresented in the students’ communities. In addition to these partnerships, our diversity hiring efforts include subscribing to and posting on diversity websites, relationships with recruitment centers at historically black colleges and universities, and sponsorship of career events focused on recruiting women and underrepresented minorities.

Employee Benefits

We offer competitive salaries and a benefits package that is designed to support the well-being of our workforce. Most employees are eligible for an annual bonus based upon individual performance, as well as the overall performance of the Company. Benefits offered to our full-time employees include, among others, medical, dental and vision insurance, a comprehensive employee assistance program to support the mental health of our employees and their families, employer-paid life and disability plans, contributions to employee retirement accounts through a Company match with immediate vesting, paid parental leave and adoption assistance, and paid time off. In addition, we offer a range of discounts, incentives and supplemental benefit programs including preventative care and fitness incentives, matching gifts program, and flex schedules that allow employees to better balance personal and professional considerations.

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Employee Training and Development

We recognize the mutual benefits for our Company and our employees to further their formal education and professional development. Our Employee Development and Education Assistance program provides financial assistance for courses, development programs and professional affiliations. Training is available to every employee and ranges from onboarding training for new hires to training sessions on general workplace skills. All employees, whether full-time or part-time, have access to an online learning management system that hosts courses and modules across a wide range of topics. Until recently, we also had a formal management development program for many years, which we are re-forming due to the changing environment related to our COVID-19 reopening plan.

We have a formal, annual performance review process. This provides managers and employees opportunities to discuss job responsibilities, encourage strengths and identify opportunities for development.

Employee Engagement

We believe soliciting candid employee feedback is a means to further the Company’s goals and value the opinions and diverse perspectives of our employees. We conduct an annual anonymous engagement survey, as well as occasional voluntary focus group sessions to better assess how motivated and engaged our employees are to perform their best each day.

Our last annual employee engagement survey, conducted in November 2021, had an 84% participation rate. Results were positive and compared favorably to other companies in the financial services industry that participated in the same survey. The top words to describe our culture included: flexible, supportive, inclusive, collaborative, accountable, teamwork, professional, and respectful. We believe this demonstrates a positive perception of the Company’s culture among our employees.

COVID-19 Response

In July 2021, after almost a year and a half of our offices being closed to all non-essential staff due to COVID-19, we reopened our offices on a voluntary basis. We built a reopening plan that reflected the shared goals and needs of our employees and business, placing an emphasis on remaining safe, productive and connected. Safety measures and procedures have been implemented throughout our offices so staff working in the office remain safe. We expect our work model to continue to develop organically, and have designed it to allow for improved work-life balance for all of our employees. This work model has helped us to attract and retain key talent in a competitive job market.

Our Communities

We believe it is important to engage with and provide support to our communities, and to encourage and support our employees as they volunteer time and resources to community-based charitable organizations. We have two internal committees staffed by employees at various levels that identify and support our charitable and volunteer involvement in the Richmond, Virginia and Raleigh, North Carolina communities, as well as the other communities in which we have offices. In addition, we have a Matching Gifts Program to support our employees’ contributions to their preferred charitable organizations, and we donate information technology equipment no longer needed by the Company to an organization that refurbishes computers at low or no cost to qualifying veterans or support organization.

Compensation of Directors

Our non-employee directors (excluding Mr. Abram, whose director compensation is described below) receive an annual cash retainer in the amount of $125,000 per year, payable in four equal installments at the beginning of each quarter, and a restricted stock unit (“RSU”) award with a fair market value of $50,000 per year. The awards of RSUs are made from the Non-Employee Director Plan and vest in full on the first anniversary of the date of the grant.

In addition to the aforementioned compensation, the Chairman of our Audit Committee is paid additional cash compensation in the amount of $25,000 per year for service in such capacity. No other committee chairman or committee member receives additional compensation for such service.

Mr. Abram, as our Non-Executive Chairman, is paid a retainer of $18,750 per month in cash, for such service, which amount is paid to him monthly.

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The following table sets forth information concerning compensation earned by our non-employee directors during the year ended December 31, 2021.

Name	Fees Earned or Paid in Cash(1) ($)			Stock Awards(2) ($)			All Other Compensation(3) ($)			Total ($)
J. Adam Abram		$	225,000			—			—		$	225,000
Thomas L. Brown		$	22,758			—			—		$	22,758
Janet R. Cowell		$	125,000		$	49,989		$	1,378		$	176,367
Kirstin M. Gould		$	22,758			—			—		$	22,758
Christopher L. Harris		$	102,582		$	49,989		$	2,273		$	154,844
Jerry R. Masters		$	150,000		$	49,989		$	1,378		$	201,367
Michael T. Oakes		$	125,000		$	49,989		$	1,378		$	176,367
Patricia H. Roberts		$	125,000		$	49,989		$	1,378		$	176,367
Ollie L. Sherman, Jr.		$	125,000		$	49,989		$	1,378		$	176,367
Sundar S. Srinivasan		$	125,000		$	49,989		$	1,378		$	176,367

(1)

The cash compensation paid to Messrs. Harris and Brown, and Ms. Gould was prorated based upon the portion of the year that such individuals served as directors during 2021. Mr. Harris served as a director until the expiration of his term as a Class I director at our 2021 Annual Meeting, at which time Mr. Brown and Ms. Gould joined the Board as Class I directors.

(2)

Represents the grant date fair value of restricted share units awarded under the 2014 Non-Employee Director Incentive Plan (the “2014 Director Plan”), calculated in accordance with FASB ASC Topic 718.

(3)

Represents dividends paid to directors that accrued on unvested restricted share units and were paid at the time awards vested.

Share Ownership Guidelines

In July 2022, the Board, at the recommendation of the Compensation Committee of the Board, adopted share ownership guidelines (the “Guidelines”) to more closely align the financial interests of the Company’s directors and executive and other senior officers with those of the Company’s shareholders. Pursuant to the Guidelines, within five years of becoming subject to the Guidelines, (i) non-employee directors are required to beneficially own common shares with a fair market value equivalent to three times their annual cash retainer, (ii) the Company’s Chief Executive Officer is required to beneficially own common shares with a fair market value equivalent to five times his annual base salary, and (iii) other executive officers and designated members of the senior management team of the Company are required to beneficially own common shares with a fair market value equivalent to three times their annual base salary. For additional information regarding the requirements of our share ownership guidelines, see, “Executive Compensation — Compensation Discussion and Analysis — Share Ownership Guidelines.”

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EXECUTIVE OFFICERS

The following table identifies each of our executive officers and their age as of August 15, 2022:

Frank N.
D’Orazio

Sarah C.
Doran

Richard J.
Schmitzer

Terence M.
McCafferty

Daniel J.
Heinlein

Michael J.
Hoffmann

Jeanette L.
Miller

Chief Executive Officer

Chief Financial Officer

President and Chief Executive Officer of the Excess and Surplus Lines segment

President and Chief Executive Officer of the Specialty Admitted Insurance segment

President and Chief Executive Officer of the Casualty Reinsurance segment

Group Chief Underwriting Officer

Chief Legal Officer

The following biographical information is furnished regarding each of our executive officers, excluding Mr. D’Orazio, whose biographical information is included in the section “Board of Directors and Corporate Governance.”

SARAH C. DORAN

Sarah C. Doran has served as the Company’s Chief Financial Officer since January 2017. Ms. Doran also serves as a Director of our U.K. holding company and a director and officer of most of our domestic subsidiaries. Before joining the Company, Ms. Doran served as Senior Vice President, Strategy, Investor Relations and Treasurer of Allied World Assurance Company Holdings, AG, a global provider of property, casualty and specialty insurance and reinsurance, since April 2013. Prior to that, Ms. Doran worked as an investment banker in the Financial Institutions Group of Barclays and Lehman Brothers. Ms. Doran received an M.B.A. from the University of Chicago and a B.A. in Government from the University of Notre Dame.

RICHARD J. SCHMITZER

Richard J. Schmitzer has served as the President and Chief Executive Officer and a director of James River Insurance Company and our other subsidiaries in our Excess and Surplus Lines segment since March 2010. He joined James River Insurance Company in July 2009 as Senior Vice President and Chief Underwriting Officer. Prior to that, Mr. Schmitzer served nineteen years at Scottsdale Insurance Company, a subsidiary of Nationwide Mutual, where he served in a variety of underwriting and underwriting management roles, most recently as Vice President of Brokerage, Professional Liability and Programs. Mr. Schmitzer received his B.S. in Business Administration from Central Michigan University.

TERENCE M. MCCAFFERTY

Terence M. McCafferty has served as President and Chief Executive Officer and a director of Falls Lake National Insurance Company and our other subsidiaries in our Specialty Admitted Insurance segment since joining the Falls Lake Insurance group in October 2018. Prior to that, he served from 2015 to 2018 as Head of Group Captives and Alternative Risk at Zurich Insurance Group. From 2006 to 2015, he served as Chief Operating Officer at Zurich Programs and Direct Markets. From 2000 to 2006, he held multiple Vice President positions at Farmers Insurance Group, a property and casualty insurance company, including in Finance Operations, Corporate Planning and property and casualty insurance operations. He served as Assistant Vice President at Zurich Personal Insurance, Recreational Products, from 1998 to 2000. Mr. McCafferty began his career as an auditor at Ernst & Young. He has also worked at Great American Insurance in Internal Audit, Financial Reporting and Product Management. Mr. McCafferty received his M.B.A. in Finance from Xavier University and B.A. in Finance and Accounting from Miami University.

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DANIEL J. HEINLEIN

Daniel J. Heinlein has served as the President and Chief Executive Officer and a director of JRG Reinsurance Company Ltd. (“JRG Re”), the Company’s subsidiary engaged in third-party casualty reinsurance business, since April 2018. He most recently held the position of Vice President of Underwriting for JRG Re, and in different positions with increasing responsibility at JRG Re from the time he joined the company in 2012. Prior to that, Mr. Heinlein served as Assistant Vice President at Willis Re Inc., a risk management consulting company. Mr. Heinlein is a graduate of Appalachian State University with a B.S. in Business Administration with majors in Finance and Banking and Risk Management and Insurance.

Michael J. Hoffmann

Michael J. Hoffmann has served as the Company’s Senior Vice President, Chief Underwriting Officer since November 2021. Mr. Hoffmann also serves as a director of JRG Reinsurance Company Ltd., and our other subsidiaries in our Casualty Reinsurance segment. Before joining the Company, Mr. Hoffmann served as Head of Risk & Ceded Reinsurance at Everest Insurance Company (“Everest”), a division of Bermuda-based insurer and reinsurer Everest Re Group. Prior to Everest, Mr. Hoffmann spent 15 years at Allied World, a global provider of property, casualty and specialty insurance and reinsurance, where he most recently served as Global Insurance Chief Underwriting Officer. Prior to Allied World, Mr. Hoffmann spent 14 years with Chubb in a variety of roles in the U.S. and Bermuda. Mr. Hoffmann received a B.A. in History from Swarthmore College.

Jeanette L. Miller

Jeanette L. Miller has served as the Company’s Chief Legal Officer since April 2021, and prior to that served as the Company’s Assistant General Counsel since October 2018. Ms. Miller also serves as an officer of James River Group, Inc. Before joining the Company, Ms. Miller served as Corporate Counsel & Deputy Compliance Officer at International Farming Corporation LLC, a privately owned institutional investment manager specializing in agriculture, from May 2017 to October 2018, and as Assistant General Counsel at CIFC LLC, an asset manager based in New York specializing in alternative credit, from December 2011 to June 2016. From 2006 to 2011, Ms. Miller was an attorney with Milbank LLP in New York in its Alternative Investments Practice. Ms. Miller received a B.S. in Business Administration from the University of Maine and a Juris Doctor degree from Columbia Law School.

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EXECUTIVE COMPENSATION

Compensation Discussion and Analysis

This Compensation Discussion and Analysis provides information about the Company’s compensation philosophy, objectives and other relevant policies applicable to our executive officers who are named in the Summary Compensation Table below (our “named executive officers”), and the material factors relevant to an analysis of these policies and decisions. The named executive officers for 2021 are:

•

Frank N. D’Orazio, our Chief Executive Officer;

•

Sarah C. Doran, our Chief Financial Officer;

•

Richard J. Schmitzer, the President and Chief Executive Officer of James River Insurance Company and our other subsidiaries engaging in our excess and surplus lines insurance business;

•

Terence M. McCafferty, the President and Chief Executive Officer of Falls Lake National Insurance Company and our other subsidiaries engaging in our specialty admitted insurance business;

•

Daniel J. Heinlein, the President and Chief Executive Officer of JRG Re, our subsidiary engaging in our third-party casualty reinsurance business; and

•

Robert P. Myron, who served as our President and Chief Operating Officer until his retirement on July 31, 2021.

Compensation Philosophy and Objectives

In designing and implementing our executive compensation program, the Compensation Committee of the Board (which for purposes of this Executive Compensation discussion we refer to as the “Committee”), and the Board, seek to achieve three principal objectives:

First, to establish compensation on a fair and reasonable basis that is competitive with our peers in the specialty insurance and reinsurance business, so that we may attract, motivate and retain talented executive officers.

Second, to create an alignment of interests between our executive officers and shareholders. For this purpose, a portion of each executive officer’s compensation consists of one or more equity awards.

Finally, we seek to reward performance that supports our principles of building long-term shareholder value overall and to recognize individual performance that contributes to the success of our Company.

The principal elements of our compensation program for our executive officers are base salary, a discretionary cash bonus and equity awards.

In determining how to best achieve our compensation objectives, the Committee maintains flexibility in order to react to changing conditions and circumstances. For example, in February 2022, the Committee took action to provide for reduced discretionary cash bonuses as compared to target levels for several of our named executive officers, but granted larger equity awards. This action was primarily motivated by our 2021 performance and a desire to further align executive officer compensation with the interests of our shareholders.

Role of Compensation Committee and our Executive Officers in Setting Executive Compensation

The Committee assists our Board with reviewing the performance of our management in achieving corporate goals and objectives and seeking to assure that our executives are compensated effectively in a manner consistent with our strategy, competitive practice and the requirements of the appropriate regulatory bodies. Toward that end, the Committee, among other responsibilities, makes recommendations to our Board regarding director and executive officer compensation and administers our equity compensation plans. The Committee determined its 2021 compensation recommendations for the Board following consultation with Mr. D’Orazio as our Chief Executive Officer, and input from Mr. Abram, our non-Executive Chairman and former Chief Executive Officer, who attended Committee meetings, but did not participate in any approval of the Committee in determining executive officer compensation. Mr. D’Orazio made recommendations to the Committee as to the compensation of other executive officers, and attended portions of Committee sessions where executive officer compensation was discussed. Mr. D’Orazio was not involved in any deliberations regarding his own compensation.

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Weighting of Compensation Components

As a general guideline, we use a target allocation of one-third of an executive’s total compensation to base salary, one-third to bonus and one-third to equity awards. When determining the amount of each element of compensation, however, there may be differences due to multiple factors, including market conditions, individual and Company performance and our desire to attract and retain executive officers. For 2021, actual compensation paid differed from these target allocations, in that in February 2022 the Board approved awards for certain officers that included a lower discretionary cash bonus, and a greater amount of compensation in the form of discretionary equity. The lower discretionary cash bonuses were primarily in response to the Company’s 2021 performance, and the greater amount of discretionary equity was granted to further align the interests of our executive officers and our shareholders.

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Internal Pay Equity

Differences in compensation levels paid to our executive officers generally reflect their differing levels of responsibility. Our Chief Executive Officer has typically been paid the highest amount of compensation among our executive officers, reflecting reliance on the management and leadership skills of the chief executive officer position.

Executive Compensation Components

BASE SALARY

DISCRETIONARY BONUSES

EQUITY AWARDS

Base Salary. The Committee endeavors to set base salaries for executive officers at levels that enable the Company to attract and retain talented individuals and that provide fair compensation, taking into account the officer’s level of responsibility. In February 2022, the Committee recommended to the Board that Mr. D’Orazio receive a salary increase to $925,000, and Ms. Doran receive an increase to $550,000, representing increases over their 2021 salaries of approximately 8.8% and 6.4% respectively. The Committee determined the recommended amount of Mr. D’Orazio’s salary increase based in significant part on the additional responsibilities that he assumed upon Mr. Myron’s retirement, which included assuming responsibility for Mr. Myron’s former direct reports, and direct oversight responsibility of, among other departments, claims, actuarial and information technology. The Committee’s recommendation for Ms. Doran’s salary increase was determined based upon her leadership on several significant matters for the Company, as well as for retention purposes. The Committee also recommended that Messrs. Schmitzer’s, McCafferty’s and Heinlein’s salaries be increased to $650,000, $420,000 and $365,000 respectively, representing raises over their 2021 salaries of approximately 1%, 5% and 4.3%. The Board approved the salary adjustments as recommended by the Committee.

Discretionary Cash Bonuses. Discretionary cash bonuses are a form of short-term incentive compensation that the Committee may recommend to the Board in its discretion. Bonuses are typically determined as a percentage of each named executive officer’s base salary, with the target being 100% of such amount. As indicated above, in February 2022, the Committee determined to reduce cash bonuses below the target amounts in light of the Company’s performance as a whole, and performance of different segments for our segment heads. Cash bonuses awarded to our named executive officers for 2021 performance ranged between 49% to 80% of the target amount.

In determining the amount of discretionary cash bonus for the named executive officers that would be recommended to the Board, the Committee took into consideration, among other things, (i) the financial performance of the Company as a whole, including the adverse reserve development in the commercial auto book and casualty reinsurance segment, and for our segment leaders, the financial performance of their respective segment,

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(ii) individual performance, and (iii) maintaining a competitive level of compensation. The individual performance factors considered for each executive officer considered by the Committee included:

The Committee’s bonus recommendations historically have not been, and in determining 2021 bonus amounts were not, determined on a formulaic basis, and no particular weight is assigned to any of the factors considered in arriving at the Committee’s recommendations to the Board.

The Board approved cash bonuses for the named executive officers in the amounts recommended by the Committee. The table below sets forth the amount of each named executive officer’s cash bonus and the percentage that it represented as compared to such officer’s 2021 base salary.

NAME	2021 BONUS			BONUS AS A % OF 2021 BASE SALARY
Frank N. D’Orazio		$	425,000		50%
Sarah C. Doran		$	257,500		50%
Richard J. Schmitzer		$	312,917		49%
Terence M. McCafferty		$	320,000		80%
Daniel J. Heinlein		$	175,000		50%
Robert P. Myron			—		—

The 2021 bonuses payable to Mr. D’Orazio and Ms. Doran were paid in full on or before March 15, 2022, consistent with other employees of our Bermuda and U.S. holding companies. The bonuses payable to Messrs. Schmitzer, McCafferty and Heinlein, who are segment employees, were paid two-thirds on or before March 15, 2022, with the remainder to be paid on or before March 15, 2023, provided that they remain employed by the Company at the time bonuses are paid in the ordinary course.

Equity Awards. Equity awards are made to our executive officers from the Company’s 2014 Long-Term Incentive Plan (the “2014 LTIP”). The equity awards are long-term compensation intended to align the interests of our executive officers with our shareholders. The equity awards are also designed to retain and motivate our executive officers, in that they typically vest in equal installments over a three-year period following the grant date.

Our annual equity awards have customarily been made in February on the day before distribution of our fourth quarter and fiscal year-end earnings release following the close of trading on such date. This practice was used for many years because the annual awards were made in conjunction with our February Board and committee meetings, which have customarily been scheduled the day before distribution of our fiscal year-end earnings release. In July 2021, the Committee and Board approved a modification of this practice so that going forward, starting in 2022, the grant date, and therefore pricing, for our annual February equity awards will be on the second trading day following the public dissemination

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of our fiscal year-end earnings release. The Committee and Board made this change so that the number of shares that are subject to awards would take into account the trading price of our shares after the markets respond, positively or negatively, to our announced financial results.

2021 Equity Awards

In determining the value of the 2021 equity awards for our named executive officers, the Committee conferred with Mr. D’Orazio and Mr. Abram. Among other items, the parties considered (i) the 2020 financial performance of the Company as a whole, including, where applicable, the performance of the commercial auto division, and, for each segment leader, the 2020 financial performance of their respective segment, (ii) 2020 individual performance, and (iii) maintaining a competitive level of compensation. In addition, Mr. D’Orazio, Mr. Abram and the Committee took into consideration the following factors for each executive:

•

For Ms. Doran, her leadership in the continued improvement in the Company’s financial reporting function, as well as her strong relationship with the investment community;

•

For Mr. Schmitzer, the profitable growth in the core excess and surplus lines divisions;

•

For Mr. McCafferty, the profitability and growth in the Specialty Admitted Insurance segment, including the addition of new programs to the segment;

•

For Mr. Heinlein, his leadership of the casualty reinsurance segment; and

•

For Mr. Myron, his assistance to Mr. D’Orazio in his transition to his role as Chief Executive Officer.

The Committee recommended to the Board for approval, and the Board approved, the value of the restricted stock unit (“RSU”) awards to the named executive officers.

The grant date fair market value of the RSU awards received by each named executive officer, and the number of common shares awarded based upon the fair market value of the common shares on the date of grant, are as follows:

NAME	2021 RSU FMV ON GRANT DATE			NUMBER OF SHARES REPRESENTED BY RSU
Frank N. D’Orazio			—		—
Sarah C. Doran		$	249,994		4,976
Richard J. Schmitzer		$	329,574		6,560
Terence M. McCafferty		$	386,245		7,688
Daniel J. Heinlein		$	169,912		3,382
Robert P. Myron		$	349,972		6,966

The above equity awards vest in equal installments over a three-year period following the grant date.

In consideration of the award of RSUs that Mr. D’Orazio received in November 2020 upon joining the Company, he did not receive a new award in February 2021. Mr. Myron’s February 2021 RSU award was forfeited in accordance with its terms at the time of his retirement.

2022 Equity Awards

In determining the recommended value of RSU awards to be made to our executive officers in February 2022, the Committee considered the same performance factors identified in the determination of the amount of discretionary cash bonuses in February 2022 identified above, and the Committee’s desire to further align the interests of our executive officers and our shareholders. The Committee recommended to the Board for approval, and the Board approved, the value of the RSU awards to the named executive officers.

NAME	2022 RSU FMV ON GRANT DATE			NUMBER OF SHARES REPRESENTED BY RSU
Frank N. D’Orazio		$	1,274,998		62,195
Sarah C. Doran		$	590,236		28,792
Richard J. Schmitzer		$	642,388		31,336
Terence M. McCafferty		$	399,996		19,512
Daniel J. Heinlein		$	402,497		19,634

The above equity awards vest in equal installments over a three-year period following the grant date.

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Welfare Benefits and Perquisites. Our named executive officers are provided welfare benefits that are generally the same as our other employees, such as Company-paid life insurance, contributions to the Company’s 401(k) Plan, medical, dental and vision plan coverage and long and short-term disability insurance.

In addition to the above benefits, Mr. Heinlein and Ms. Doran are entitled to receive benefits based upon their required work for the Company in Bermuda, and Mr. Myron was entitled to such benefits prior to his retirement. The Company implemented these benefits for its executive officers in 2008, when the Company formed its holding and reinsurance company in Bermuda. These benefits are:

•

payment of certain housing expenses in Bermuda for Mr. Heinlein and formerly for Mr. Myron;

•

payment of travel costs for Mr. Heinlein and formerly Mr. Myron; and

•

tax equalization gross-up payments or other Bermuda tax payments (collectively, “Tax Equalization Payments”) to which any of Mr. Heinlein, Ms. Doran, and formerly Mr. Myron, may be subject with respect to payments or benefits that such named executive officer receives under his or her employment agreement.

We make the above housing, travel and tax benefits available to the specified named executive officers employed by the Company or its Bermuda subsidiary based upon the unique challenges of performing work in the Bermuda market, including the cost of living and maintaining a residence, travel to and from the island and additional tax expenses primarily resulting from the housing and travel benefits. We believe that providing these benefits is common practice for other Bermuda based insurers, and is consistent with our goal to attract and retain talented executive officers.

The Company also paid for Mr. Myron’s family to occasionally travel to Bermuda. Any incremental costs to the Company associated with such travel was charged to Mr. Myron.

Leadership Recognition Program. In addition to the other benefits paid to our named executive officers, Mr. Schmitzer receives an annual retention payment under the James River Management Company, Inc. Leadership Recognition Program (the “Recognition Program”). The Recognition Program was adopted by James River Management Company, Inc., one of the Company’s subsidiaries, effective September 30, 2011, to help attract and retain key employees of our excess and surplus lines business. Under the Recognition Program, the Chief Executive Officer of our U.S. holding company, or in the case of executive officers of the Company, our Board of Directors, upon recommendation of the Compensation Committee, selects the employees who participate in the Recognition Program and determines the annual dollar amount to be credited to each participant’s account under the Recognition Program. The dollar amount credited to a participant’s account under the Recognition Program each year is paid to the participant in five equal annual installments, commencing as of the end of the second plan year beginning after the year in which the amount was credited to the participant’s account. Participants must be employed at the time of payment of an installment to be entitled to receive the payment, subject to certain exceptions described under “Potential Payments upon Termination or Change of Control”.

All amounts credited to a participant’s account remain unvested until paid and may be reduced, modified or terminated at the sole discretion of the Company. The Company may amend, modify or terminate the Recognition Program at any time, including, without limitation, to comply with the provisions of Section 409A of the Internal Revenue Code of 1986, as amended, so as not to trigger any unintended tax consequences prior to the distribution of benefits under the program. There are no vested rights to amounts under the Recognition Program at any time prior to the payment of such amounts, and all amounts under the Recognition Program are at all times discretionary obligations of the Company, which may be reduced or terminated by the Company at any time. Except as otherwise stated above, the Recognition Program is administered by the board of directors of our U.S. holding company.

In 2017, we determined to cease making new dollar credits to accounts under the Recognition Program. The determination was made in recognition of the fact that following our 2014 initial public offering, we were able to make regular equity awards to our executives. All amounts previously credited to Mr. Schmitzer’s account will continue to be paid in accordance with the terms of the Recognition Program.

Mr. Schmitzer received a payout under the terms of the Recognition Program in 2021 of $147,000 based on amounts credited to his account in prior years. Mr. Schmitzer’s last payment under the program will be in 2023.

Share Ownership Guidelines

In July 2022, the Board, at the recommendation of the Committee, adopted share ownership guidelines (the “Guidelines”) to more closely align the financial interests of the Company’s directors and executive and other senior officers with those of the Company’s shareholders. Pursuant to the Guidelines, within five years of becoming subject to the Guidelines, (i) non-employee directors are required to beneficially own common shares with a fair market value equivalent to three times their annual cash retainer, (ii) the Company’s Chief Executive Officer is required to beneficially own common shares with a fair market value equivalent to five times his annual base salary, and (iii) other executive officers and designated members of the senior management team of the Company are required to beneficially own common shares with a fair market value equivalent to three times their annual base salary. In calculating ownership under the Guidelines, common shares subject to restricted share units with time-based vesting requirements are counted as owned shares (but shares subject to performance restricted share units will not be).

For purposes of the Guidelines, the fair market value of the common shares will be established using the greater of (i) the average closing price of the common shares on the Nasdaq Stock Market for the 30 trading day period immediately prior to the applicable determination date (the “Market Price”) or (ii) the price paid at the time of purchase, or, if the shares were not purchased (for example, if the shares were acquired on exercise of an equity award), the closing price of the common shares on the Nasdaq Stock Market on the date of acquisition.

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Notwithstanding the foregoing, pursuant to the Guidelines, (a) shares subject to eligible unvested restricted share units shall be valued at the greater of (i) the Market Price or (ii) the closing price on the Nasdaq Stock Market on the grant date, and (b) shares received upon the vesting of RSUs shall be valued at the greatest of (i) the Market Price, (ii) the closing price on the Nasdaq Stock Market on the grant date, or (iii) the closing price of shares on the Nasdaq Stock Market on the date of vesting.

Pursuant to the Guidelines, covered persons are required to retain 100% of the net-after-tax shares received for one year following the vesting or settlement of an equity award regardless of whether the Guidelines have been met, and additionally, until a covered participant comes into compliance with the applicable ownership level, such person must retain 75% of the net-after tax shares received upon vesting or settlement of an equity award.

Termination Benefits

Each of our named executive officers is party to an employment agreement with us that provides for certain benefits if his or her employment is terminated under certain circumstances. This arrangement provides the named executive officers with a core level of assurance that their actions on behalf of the Company and its shareholders can proceed without the potential distraction of short-term issues that may affect the Company (e.g., a strategic transaction involving the Company) and helps ensure that our named executive officers continue to act in the best interests of the Company. In addition, the agreements contain measures that protect the Company past the date of the named executive officer’s termination, such as confidentiality, non-compete and non-solicitation requirements and the requirement that named executive officers execute a general release in favor of the Company in order to receive benefits. Named executive officers may also receive benefits with respect to unvested equity awards under our 2014 LTIP and in the case of Mr. Schmitzer, the Recognition Program. The key terms of the separation arrangements are described below in “Potential Payments Upon Termination or Change in Control”.

2022 Compensation Developments

The Company, with the Committee’s approval, retained Mercer (US), Inc. (“Mercer”) to assist the Committee in evaluating the compensation of the Company’s senior executive officers. As part of the engagement, Mercer assisted the Committee in developing a peer group to assess the design of our executive compensation program and to compare executive pay levels. The Committee used the peer group information in the development of variable cash bonuses under a new short-term incentive plan and variable equity compensation under a new long-term incentive plan. In July 2022, the Board, upon the recommendation of the Committee, approved the James River Group Holdings, Ltd. Short-Term Incentive Plan (the “STI Plan”), and granted initial award opportunities under such plan to the Company’s senior management team, including the named executive officers, for performance during the 2022 fiscal year, identified the Company’s senior management team as participants under such plan, including the named executive officers, as well as approved the James River Group Holdings, Ltd. Long-Term Incentive Plan (the “LTI Plan”).

The Committee believes that the adoption of the STI Plan and the LTI Plan provide the following benefits to our compensation program:

•

better align executive pay with Company performance, in that a significant portion of each executive officer’s pay opportunity is in the form of variable, performance-based short-term and long-term incentive awards, which are earned based on achievement of pre-established performance goals;

•

enhance the transparency of how the amount of short-term incentive payment and value of equity awards are determined;

•

adopt short-term incentive payment and equity award methodologies that are more consistent with the Company’s peer group, as identified below; and

•

establish pre-set maximum awards so that even if performance is above the maximum goal, the Company will nonetheless pay no more than the pre-set amount.

The Committee believes that the STI Plan and LTI Plan support best practices, prudent management of our business and properly align pay with performance.

Peer Group. With Mercer’s assistance, the Committee identified a peer group based upon the following factors:

•

companies engaged in property & casualty insurance; and

•

companies with total revenue and assets that were approximately 0.5x to 2.0x compared to the Company.

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Based upon these criteria, the Committee identified the following 14 companies as its peer group to help develop the STI Plan and LTI Plan:

	Amerisafe, Inc.				Kinsale Capital Group, Inc.
	Argo Group International Holdings, Ltd.				ProAssurance Corporation
	Donegal Group Inc.				RLI Corp.
	Employers Holdings, Inc.				SiriusPoint Ltd.
	Global Indemnity Group, LLC				United Fire Group, Inc.
	Hallmark Financial Services, Inc.				United Insurance Holdings Corp.
	HCI Group, Inc.				United Insurance Holdings, Inc.

STI Plan and Incentive Awards for 2022. The STI Plan is designed to provide incentives to designated senior officers of the Company to achieve certain financial and strategic performance targets and to link executive compensation to shareholder results by rewarding competitive and superior performance. Under the STI Plan, participants have the opportunity to receive a cash incentive award based upon the level of achievement of the performance goals over the period of January 1, 2022 through December 31, 2022. The named executive officers of the Company are among the designated participants for the 2022 performance period.

Based upon a review of the peer group’s short-term compensation practices and the Company’s strategic plan and historical performance levels, the Committee recommended to the Board, and the Board approved, the use of three performance metrics. Two of these are financial performance metrics, adjusted combined ratio and adjusted earnings before interest and taxes (EBIT), which are non-GAAP financial measures, and the third is the achievement of specified strategic goals. The Committee believes that performance metrics based on combined ratio and EBIT are appropriate, as they are industry standard measures of profitability.

For a member of our senior management with Company-wide responsibility, which includes Mr. D’Orazio and Ms. Doran, adjusted Company combined ratio, adjusted EBIT and the strategic goals are each weighted one-third in determining the actual incentive award payout. For a member of senior management who is a business segment leader or whose responsibilities are primarily focused on a single business segment, including Messrs. Schmitzer, McCafferty and Heinlein, the only variation in the performance metrics and weighting is that the adjusted combined ratio metric is split evenly between the Company’s adjusted combined ratio and the adjusted combined ratio of the applicable segment that such member of senior management performs services for, so each is weighted 16.665% of such person’s short term incentive opportunity.

Calculation of Adjusted Combined Ratio Metric

The Company’s adjusted combined ratio is calculated as the combined ratio of the Company on a consolidated basis, calculated prior to the effect of favorable or unfavorable prior year reserve development for which the Company’s subsidiaries ceded the risk under retroactive reinsurance agreements and the related changes in the amortization of the deferred gain.

For each segment, adjusted combined ratio is calculated as the segment’s combined ratio, calculated prior to the effect of favorable or unfavorable prior year reserve development for which such segment ceded the risk under retroactive reinsurance agreements, if any, and the related changes in the amortization of the deferred gain.

Calculation of Adjusted EBIT

Adjusted EBIT is calculated as net income of the Company before income taxes and interest and excluding the portion of favorable or unfavorable prior year reserve development for which the Company’s subsidiaries ceded the risk under retroactive reinsurance agreements and the related changes in the amortization of the deferred gain.

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Payouts for achievement of threshold, target and maximum performance levels by named executive officers are set at 50%, 100% and 150% of the target opportunity, respectively. Performance falling between these levels is determined by linear interpolation. Threshold, target and maximum payouts for each of the named executive officers is set forth below, with the target payout amount equal to their 2022 annual base salary.

EXECUTIVE OFFICER	THRESHOLD PAYOUT			TARGET PAYOUT			MAXIMUM PAYOUT
Frank N. D’Orazio		$	462,500		$	925,000		$	1,387,500
Sarah C. Doran		$	275,000		$	550,000		$	825,000
Richard J. Schmitzer		$	325,000		$	650,000		$	975,000
Terence M. McCafferty		$	210,000		$	420,000		$	630,000
Daniel J. Heinlein		$	182,500		$	365,000		$	547,500

The Committee will determine and recommend to the Board for approval the aggregate payout for the 2022 performance period in the first quarter of 2023. The Committee has discretion to adjust final results in the event of unusual or nonrecurring events.

To receive a payout, a participant must remain employed through the settlement of the award, subject to certain exceptions for (i) separation due to death or disability (in which case, payment is made at target level, pro-rated for the period employed), (ii) a qualifying retirement, termination without cause, termination by reason of non-renewal by the Company of the executive officer’s contract or resignation by the executive for good reason (in which case, payment is made based upon actual performance for the full performance period, pro-rated for the period employed), or (iii) a change in control of the Company prior to settlement of the award, followed by termination without cause of the participant, the Company’s non-renewal of the participant’s employment contract, or resignation by the participant for good reason (in which case, payment is made based upon actual performance for the full performance period, pro-rated for the period employed).

LTI Plan. The LTI Plan is designed to align compensation of designated senior officers of the Company, including the named executive officers, with Company performance and shareholder interests over the long-term. Awards under the LTI Plan will be made in the form of performance restricted share units (“PRSUs”). The Compensation Committee determined to delay the issuance of the initial awards of PRSUs until February 2023 since executives were granted equity awards in February 2022 prior to adoption of the LTI Plan. The performance period for the initial awards will be January 1, 2023 through December 31, 2025. Initial awards to each of the named executive officers are intended to have a target value equal to 50% of such named executive officer’s 2022 annual base salary, with the named executive officer receiving a service based award of restricted share units with a fair market value equal to 50% of the executive officer’s 2022 base salary. Each PRSU will represent a contingent right to receive one Company common share based upon the level of achievement of certain performance metrics during the performance period.

Based upon a review of our peer group’s long-term compensation practices, and the Company’s own business, the Committee recommended to the Board, and the Board approved, the use of two financial performance metrics, which will be evenly weighted. The financial performance metrics are (i) the Company’s adjusted operating return on average adjusted tangible common equity, and (ii) growth in adjusted tangible common equity per common share. Both of these measures are non-GAAP measures. The Committee chose these metrics because it believes that these measures are early indicators of the Company’s long-term financial performance.

Calculation of Adjusted Operating Return on Average Adjusted Tangible Common Equity

The Company calculates adjusted operating return on average adjusted tangible common equity for the performance period as the three-year average adjusted net operating income divided by the four-year average adjusted tangible common equity. For purposes of this calculation:

“Adjusted net operating income” is defined as net income (loss) available to common shareholders excluding (i) net realized and unrealized gain (losses) on investments, (ii) the portion of favorable or unfavorable prior year reserve development for which the Company’s subsidiaries ceded the risk under retroactive reinsurance agreements and the related changes in the amortization of deferred gain, and (iii) certain non-operating expenses, such as professional service fees related to a purported class action lawsuit, various strategic initiatives, the filing of registration statements for the offering of securities, and severance costs associated with terminated employees, calculated as of December 31 of each fiscal year during the performance period.

“Adjusted tangible common equity” is defined as shareholders’ equity less goodwill and intangible assets, net of amortization, accumulated other comprehensive income, and realized and unrealized gains (losses) on investments, and plus deferred gains under retroactive reinsurance agreements entered into by the Company’s subsidiaries, calculated as of the December 31st immediately preceding the performance period and December 31 of each fiscal year during the performance period.

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Calculation of Growth in Adjusted Tangible Common Equity per Common Share

The Company calculates growth in adjusted tangible common equity per common share for the performance period as a percentage equal to the greater of (i) ((A-B)/B)/4, and (ii) 0%, where:

A = adjusted tangible common equity per common share as of the last day of the performance period; and

B = adjusted tangible common equity per common share as of the December 31st immediately preceding the performance period.

“Adjusted tangible common equity per common share” is calculated as (i) adjusted tangible common equity, divided by (ii) the number of common shares outstanding.

The number of PRSUs that will be eligible to be earned and become vested for participants will be based upon both continued employment and the achievement of the performance metrics during the performance period, with payout for achievement of threshold, target and maximum performance levels for named executive officers to be set at 50%, 100% and 200% of the target number of PRSUs, respectively. Performance falling between these levels will be determined by linear interpolation. The Committee has discretion to adjust final results in the event of unusual or nonrecurring events.

To receive a payout, a participant must remain employed through the settlement of the award, subject to certain exceptions for (i) separation due to death or disability (in which case, payment is made at target level, pro-rata for the period employed), (ii) a qualifying retirement (in which case, payment is made based upon actual performance for the full performance period, pro-rated for the period employed), or (iii) a change in control of the Company prior to the settlement of the award, followed by termination without cause of the participant, the Company’s non-renewal of the participant’s employment contract, or resignation by the participant for good reason (in which case, payment is made based upon actual performance for the full performance period, pro-rated for the period employed).

The service based RSU awards will vest in three substantially equal annual installments commencing on the first anniversary of the grant date, provided that the recipient remains employed, subject to certain exceptions for (i) separation due to death or disability (in which case, all remaining unvested RSUs would vest), (ii) a qualifying retirement (in which case, the RSUs that would vest on the next annual installment will vest, and any other remaining RSUs will be forfeited) and (iii) a change in control of the Company prior to a vesting date, followed by termination without cause of the participant, the Company’s non-renewal of the participant’s employment contract, or resignation by the participant for good reason (in which case, all remaining unvested RSUs would vest).

Response to Say-on-Pay Results

In 2018, our shareholders selected, on an advisory basis, the option to hold an advisory vote on executive compensation every year, and after giving this vote consideration, our Board selected an annual frequency to hold the advisory vote. In the 2021 advisory vote, shareholders holding approximately 82% of our common shares that were voted on the proposal voted in favor of the compensation of our named executive officers as described in our 2021 proxy statement. We note the support for our approach to compensation of our executive officers in the 2021 advisory vote, but that there was also room for improvement. Therefore, we continued our general approach when making executive compensation decisions in February 2022, but have modified our approach for future periods through the adoption of the STI Plan and LTI Plan described above, which will, among other things, better align executive pay with Company performance.

Compensation Committee Report

The members of the Compensation Committee of the Company have reviewed and discussed the Compensation Discussion and Analysis required by Item 402(b) of Regulation S-K with management and, based on such review and discussions, the Compensation Committee recommended to the Board that the Compensation Discussion and Analysis be included in our Annual Report on Form 10-K and in the definitive proxy statement for our 2022 annual general meeting of shareholders.

Compensation Committee

Patricia H. Roberts (Chairperson)
Ollie L. Sherman, Jr.
Sundar S. Srinivasan

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Summary Compensation Table

The following table provides information regarding the compensation of our named executive officers in 2021:

NAME AND PRINCIPAL POSITION	YEAR		SALARY ($)			BONUS ($)			SHARE AWARDS(1) ($)			OPTION AWARDS ($)		ALL OTHER COMPENSATION(2) ($)			TOTAL ($)
Frank N. D’Orazio, Chief Executive Officer		2021		$	850,000		$	425,000			—		—		$	42,980		$	1,317,980
Frank N. D’Orazio, Chief Executive Officer		2020		$	141,667		$	200,000		$	2,999,965		—		$	113		$	3,341,745
Sarah C. Doran, Chief Financial Officer		2021		$	512,500		$	257,500		$	249,994		—		$	35,570		$	1,055,564
		2020		$	491,667		$	250,000		$	1,099,950		—		$	67,342		$	1,908,959
		2019		$	450,000		$	410,000		$	449,981		—		$	49,506		$	1,359,487
Richard J. Schmitzer, President and Chief Executive Officer, Excess and Surplus Lines segment		2021		$	642,500		$	312,917		$	329,574		—		$	195,371		$	1,480,362
		2020		$	625,833		$	312,917		$	542,459		—		$	185,678		$	1,666,887
		2019		$	537,903			—		$	526,758		—		$	210,958		$	1,275,619
Terence M. McCafferty, President and Chief Executive Officer, Specialty Admitted Insurance segment		2021		$	397,708		$	320,000		$	386,245		—		$	36,347		$	1,140,300
		2020		$	384,375		$	288,281		$	374,966		—		$	27,071		$	1,074,693
		2019		$	375,000		$	375,000		$	219,984		—		$	308,820		$	1,278,804
Daniel J. Heinlein, President and Chief Executive Officer, Casualty Reinsurance segment		2021		$	348,317		$	175,000		$	169,912		—		$	226,270		$	919,499
		2020		$	338,250		$	169,950		$	329,978		—		$	222,752		$	1,060,930
		2019		$	328,333		$	255,000		$	319,984		—		$	232,218		$	1,135,535
Robert P. Myron(3) Former President and Chief Operating Officer		2021		$	408,334			—		$	349,972		—		$	469,168		$	1,227,474
		2020		$	691,667		$	350,000		$	649,984		—		$	446,579		$	2,138,230
		2019		$	709,409			—		$	749,982		—		$	497,035		$	1,956,426

(1)

Represents the aggregate grant date fair value of RSUs awarded under the 2014 Long-Term Incentive Plan (the “2014 LTIP”) computed in accordance with FASB ASC Topic 718.

(2)

See the immediately following table for a breakdown of the compensation included in the All Other Compensation column.

(3)

Mr. Myron retired on July 31, 2021. All of Mr. Myron’s unvested RSUs, which included all of the RSUs granted to him in 2021, were forfeited upon his retirement in accordance with the terms of the award agreements.

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The following table provides a breakdown of the amounts set forth in the All Other Compensation column of the Summary Compensation Table:

Name	401(K) PLAN CONTRIBUTION ($)			TRANSPORTATION(a) ($)			HOUSING(b) ($)			TAXES(c) ($)			RETENTION AWARD(d) ($)			ACCRUED DIVIDENDS PAID UPON VESTING OF RSU AWARDS ($)			OTHER(e) ($)			TOTAL ALL OTHER COMPENSATION ($)
Frank N. D’Orazio		$	17,400			—			—			—			—		$	25,067		$	513		$	42,980
Sarah C. Doran		$	17,400			—			—			—			—		$	17,657		$	513		$	35,570
Richard J. Schmitzer		$	17,400			—			—			—		$	147,000		$	30,458		$	513		$	195,371
Terence M. McCafferty		$	17,400			—			—			—			—		$	18,434		$	513		$	36,347
Daniel J. Heinlein		$	17,400		$	9,534		$	136,181		$	37,000			—		$	14,057		$	12,098		$	226,270
Robert P. Myron		$	17,400		$	1,926		$	95,040		$	92,594			—		$	110,209		$	151,999		$	469,168

(a)

For Messrs. Heinlein and Myron, the transportation benefit represents home leave and travel costs incurred for travel to Bermuda, as well as the cost of any occasional family travel to Bermuda paid for by the Company.

(b)

The housing benefit represents the cost of housing and utilities in Bermuda paid or reimbursed by the Company for Messrs. Heinlein and Myron. Mr. Myron’s family occasionally stayed in, and Mr. Heinlein’s family lives in, the housing paid for by the Company with such executives. There is no incremental cost allocated for family use of these homes.

(c)

The tax benefit represents Tax Equalization Payments made to Messrs. Heinlein and Myron.

(d)

Represents amount of retention award paid in 2021 pursuant to the James River Management Company, Inc. Leadership Recognition Program.

(e)

The amount shown for each named executive officer includes company-paid life insurance. The amount shown for Messrs. Heinlein and Myron also includes tax preparation services. The amount shown for Mr. Myron also includes compensation in the amount of $146,000, which he was paid for rendering consulting services to the Company following his retirement until December 31, 2021. The amount shown for Mr. Heinlein also includes club membership fees paid by the Company for the purpose of business entertainment.

Grants of Plan-Based Awards

The following table provides information regarding grants of equity awards to each of our named executive officers during 2021. All equity awards granted to our named executive officers in 2021 were in the form of RSUs and were made under our 2014 LTIP.

NAME	GRANT DATE		NUMBER OF SHARES OR STOCK OR UNITS (#)		GRANT DATE FAIR VALUE OF STOCK AND OPTION AWARDS ($)(1)
Frank N. D’Orazio		—		—			—
Sarah C. Doran		2/17/2021		4,976		$	249,994
Richard J. Schmitzer		2/17/2021		6,560		$	329,574
Terence M. McCafferty		2/17/2021		7,688		$	386,245
Daniel J. Heinlein		2/17/2021		3,382		$	169,912
Robert P. Myron		2/17/2021		6,966(2)		$	349,972

(1)

The grant date fair value of the RSUs was calculated in accordance with FASB ASC Topic 718.

(2)

Mr. Myron’s unvested RSUs were forfeited in accordance with their terms upon his retirement on July 31, 2021.

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Outstanding Equity Awards at Fiscal Year-End

The following table sets forth the outstanding equity awards held by our named executive officers on December 31, 2021. Mr. Myron’s unvested RSUs were forfeited in accordance with their terms upon his retirement, and therefore he held no outstanding equity awards on December 31, 2021.

			OPTION AWARDS									STOCK AWARDS
NAME	GRANT DATE		NUMBER OF SECURITIES UNDERLYING UNEXERCISED OPTIONS (#) EXERCISABLE		NUMBER OF SECURITIES UNDERLYING UNEXERCISED OPTIONS (#) UNEXERCISABLE		OPTION EXERCISE PRICE ($)			OPTION EXPIRATION DATE		NUMBER OF SHARES OR UNITS OF STOCK THAT HAVE NOT VESTED (#)		MARKET VALUE OF SHARES OR UNITS OF STOCK THAT HAVE NOT VESTED ($)(1)
Frank N. D’Orazio		11/2/2020(2)		—		—			—		—		41,780		$	1,203,682
Sarah C. Doran		2/20/2019(2)		—		—			—		—		3,566		$	102,736
		2/19/2020(2)		—		—			—		—		6,888		$	198,443
		10/28/2020(2)		—		—			—		—		8,281		$	238,576
		2/17/2021(2)		—		—			—		—		4,976		$	143,359
Richard J. Schmitzer		2/16/2016(3)		43,427		—		$	32.07		2/15/2023		—			—
		2/20/2019(2)		—		—			—		—		4,174		$	120,253
		2/19/2020(2)		—		—			—		—		8,304		$	239,238
		2/17/2021(2)		—		—			—		—		6,560		$	188,994
Terence M. McCafferty		2/20/2019(2)		—		—			—		—		1,743		$	50,216
		2/19/2020(2)		—		—			—		—		5,740		$	165,369
		2/17/2021(2)		—		—