Management Team

Mr. Richardson has served as CEO and a director since January 1, 2024, and became a director of Greenlight Re in March 2024 following regulatory approval; previously, he was Chief Risk and Strategy Officer at TransRe from 2014 to 2023, and before that held strategic planning and underwriting roles, including Chief Underwriting Officer at Harbour Point Re (which merged with Max Re Capital to form Alterra Re) from 2006 to 2013.

He holds a Bachelor of Science Honors degree in Mathematics from Purdue University, was a Marshall Scholar at Oxford University, and earned a Master of Business Administration in Finance from the University of Chicago.

His deep U.S. and international industry expertise, combined with experience in underwriting and strategic positions as well as strong leadership, make him ideally suited for the CEO role and to contribute valuable insights to the Board in shaping the company's go-forward strategy.

Mr. Romer has served as Chief Financial Officer since April 2023, responsible for all aspects of the Company’s finance and reporting function and as a director of GRIL since September 2023; he previously was Chief Accounting Officer and Treasurer from September 2020 to March 2023, and Reporting and Compliance Officer from 2007 to 2020, overseeing SEC reporting, periodic and annual financial reporting, internal audit, and SOX 404 processes, prior to which he was a Senior Manager at KPMG.

He holds a Bachelor of Arts degree in Business Administration from the University of Western Ontario—Richard Ivey School of Business, and is a Certified Public Accountant and member of the Chartered Professional Accountants of Canada.

Mr. O’Brien has served as Chief Executive Officer of GRIL since March 2017, playing an instrumental role in expanding the Company’s European operations and overall strategy, and was appointed Chief Operating Officer of the Company in 2024, also serving as a director of GRIL since June 2016; previously, he was Chief Executive Officer of Liberty Insurance from 2011 to 2015, establishing the insurer in the Irish market post-acquisition, and from 2001 through 2011 served as a director and Chief Operating Officer of Liberty Mutual Insurance Europe’s commercial and specialty business.

He holds a degree in Accounting and Finance from Dublin City University and is a Fellow of the Institute of Chartered Accountants in Ireland.

Mr. Curnock was appointed Group Chief Underwriting Officer in October 2024 to oversee the underwriting function of the Company, previously serving as Chief Risk Officer managing enterprise risk functions including capital modeling, exposure management, and operational risk, and prior to that worked in risk management and as an underwriter since joining the Company in July 2009; before the Company, he served at Aon as Senior Vice President as an investment banker from 2007 to 2009 and as Senior Vice President as a structured reinsurance broker from 2001 to 2007.

He holds a Bachelor of Science in Mathematics and a Ph.D. in computer science from the University of Salford.

Mr. Strommer has served as Chief Actuary since September 2018, and prior to that as Senior Actuary overseeing the Company's quarterly reserving process since joining in May 2017; before the Company, he held various managerial roles at Ernst & Young from February 2013 to May 2017 on global engagements involving transactions, pricing, reserving, capital modeling, and regulatory reporting primarily in the UK and Australia, earlier working at KPMG and spending five years at Swiss Re focused on commercial and investment-type product design, pricing, and reserving.

He holds a Bachelor of Science degree in Mathematics from Imperial College London and is a qualified actuary and Fellow of the Institute and Faculty of Actuaries in the UK.

Mr. O’Reilly has served as Head of Innovations since September 2020, overseeing all aspects of the Innovations strategy and day-to-day operations; he previously held various actuarial roles at the Company since 2013 before joining the Innovations function at its inception in March 2018, and prior to that, worked as a Senior Actuarial Analyst at Accident Fund Holdings, Inc. from 2012 to 2013 and as an Actuarial Analyst at ICW Group from 2008 to 2012.

He holds a Bachelor of Business Administration from the University of Miami with a major in Finance, a Postgraduate Diploma in Actuarial Science from the University of Leicester (UK), and is an Associate of the Casualty Actuarial Society as well as an Associate of the Society of Actuaries.

Mr. Sigmon has served as General Counsel, Chief Compliance Officer, and Corporate Secretary since April 2023, and as Chief Risk Officer of Greenlight Re since March 2025; prior to joining the Company, he was Vice President and Associate General Counsel at Everest Group, Ltd. from August 2017 to April 2023, serving as senior counsel for corporate law, capital markets, and complex transactions, previously as General Counsel for Unique Risk Underwriting at AmTrust Financial Services, Inc. from 2013 to 2017, and earlier as an associate attorney in the New York City office of an international law firm.

He holds a Bachelor of Arts degree from The George Washington University, a Juris Doctor degree with honors (cum laude distinction) from Brooklyn Law School, and an LL.M. degree from Georgetown University Law Center.