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.

Paul J. O’Shea has been a director since the Company’s formation in 2001 and is a company co-founder. Mr. O’Shea was named President of Enstar Group in December 2016. Prior to this, he served as Executive Vice President and Joint Chief Operating Officer of Enstar Group Limited from 2001, and as a director and Executive Vice President of Castlewood Limited, which is now a subsidiary of Enstar Group Limited, from 1995 until 2001. From 1985 until 1994, he served as the Executive Vice President, Chief Operating Officer and a director of Belvedere Group/Caliban Group.

Orla Gregory was appointed Chief Operating Officer in 2016. She served as Chief Integration Officer from 2015. Prior to that, she was Executive Vice President of Mergers and Acquisitions of Enstar Limited. She has been with the Company since 2003. Ms. Gregory worked as Financial Controller of Irish European Reinsurance Company Ltd. in Ireland from 2001 to 2003. She worked in Bermuda from 1999 to 2001 for Ernst & Young as an Investment Accountant. Prior to this, Ms. Gregory worked for QBE Insurance & Reinsurance (Europe) Limited in Ireland from 1993 to 1998 as a Financial Accountant.

Paul Brockman was appointed Chief Claims Officer in September 2020. He served as President & Chief Executive Officer of Enstar (US) Inc. from July 2016. Prior to that, he was Chief Operating Officer of Enstar (US) Inc. from 2014-2016, and from 2012-2014, he served as Senior Vice President, Head of Commutations in the US. Before joining Enstar, he worked as Head of Reinsurance for Resolute Management Services UK Ltd. and prior to that at Equitas.

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.

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.