Dominic Silvester serves as a director and as the Chief Executive Officer of Enstar Group Limited. Mr. Silvester has served as a director and the Chief Executive Officer since the Company’s formation in 2001. In 1993, Mr. Silvester started a business venture in Bermuda to provide run-off services to the insurance and reinsurance industry. In 1995, the business was assumed by Castlewood Limited, which is now a subsidiary of Enstar Group Limited, and Mr. Silvester served as Chief Executive Officer. From 1988 until 1993, Mr. Silvester served as the Chief Financial Officer of Anchor Underwriting Managers Limited.

Dominic Silvester started his career in 1982 as a trainee at Littlejohn Frazer Chartered Accountants in London, spending four years at the firm and qualifying as a Chartered Accountant in 1986. Mr. Silvester then took up the role of Audit Senior at Deloitte & Touche Bermuda in 1986, working primarily on the audit of Bermuda-domiciled captive insurance companies.

In 1988, Dominic Silvester was appointed Vice President of Finance at Aon Corporation in Hamilton, Bermuda. Mr. Silvester ran all the financial aspects of Aon’s Bermuda-based MGA, called Anchor Underwriting Managers.

After five years at Aon Corporation, Dominic Silvester became CEO of Castlewood Limited, which acquired captive insurance companies that were in run-off. Castlewood Limited was formed to acquire Paumanock Insurance Company from Grumman Corporation. Castlewood Limited secured early transactions during the initial years with Wackenhut Corporation, Smith International, Altel Corporation, Allied Domecq, and Foster Wheeler.

Following a transaction in 2001, when Mr. Silvester brought on JC Flowers & Co and Stone Point Capital as shareholders, many larger transactions followed, including River Thames Insurance Company, Turegum Insurance Company, and Gordian Insurance Company. In 2007, Enstar Group Limited then acquired the Australian closed reinsurance and p/c insurance operations of AMP for $518m, leading to Castlewood Limited merging with Enstar Group Limited on 31 January 2007. The following day, Enstar Group Limited has traded on the NASDAQ with Dominic Silvester serving as a director and as the Chief Executive Officer.

Since 2002, Dominic Silvester has held the role of Director of Saracens Football Club, an English professional rugby union club based in London, England. Mr. Silvester has been on the committee of the Make a Difference Leadership Foundation (MAD) since 2003. The MAD foundation, based in Cape Town, South Africa, identifies, supports, and develops future leaders in the country by offering scholars assistance in the areas of mentorship and personal, academic and leadership development. Mr. Silvester is also a Non-Executive Chairman of Advent Sport & Event Management, a role he has held since 2009.

Dominic Silvester was educated at Blackrock College in Dublin, Ireland, before obtaining a Bachelor of Science honours degree in Accounting and Economics at the University of Hull, England.

Orla Gregory was appointed President in March 2023 after serving as Chief Financial Officer. Prior to this, she was named Acting Chief Financial Officer in September 2021 and served as the Company's Chief Operating Officer since 2016. Since joining the Company in 2003, Ms. Gregory has held increasingly senior roles, including Chief Integration Officer from February 2015 and Executive Vice President of Mergers and Acquisitions of our subsidiary, Enstar Limited, from May 2014. Prior to this, she held a number of finance positions in the Insurance Industry both in Ireland and Bermuda.

Ms. Gregory was appointed to the Enstar Board of Directors in February 2022.

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

Paul Brockman was appointed Group Chief Commercial Officer in October 2024. Mr. Brockman joined Enstar in 2012 and has held several senior positions during this time, including Group Chief Operating Officer from March 2023 to October 2024, whilst also serving as Interim CEO of Enstar EU from January 2024 to July 2024 and Group Chief Claims Officer from September 2020 to January 2024. Prior to this he served as President & Chief Executive Officer of Enstar (US) Inc. from July 2016 to September 2020, President & Chief Operating Officer of Enstar (US) Inc. from 2014 to 2016, and Senior Vice President, Head of Commutations from 2012 to 2014. Mr. Brockman began his career in the Lloyd’s and London market in 1992, spending 20 years in senior roles at Resolute Management Services and Equitas.

Matthew (Matt) Kirk was appointed Chief Financial Officer in March 2023 after serving as Group Treasurer since 2020 where he was responsible for treasury, capital management, and investor relations. Previously, Mr. Kirk held executive roles at Sirius International Insurance Group, including Group Treasurer and President, Managing Director of Sirius Investment Advisors. Mr. Kirk was also an Assurance and Business Advisory Manager at Arthur Andersen. He is also a Certified Public Accountant (inactive).

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

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

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

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