Leadership Team

Paul O’Shea
Executive Chairman of StarStone and President of Enstar

Paul J. O’Shea was appointed Executive Chairman of StarStone and President of Enstar, of which he is co-founder, in December 2016. Paul has more than 30 years of experience in the re/insurance industry. He has served as Executive Vice President and Joint-Chief Operating Officer and a member of Enstar’s Board of Directors since 2001. In this role he spearheaded more than 70 acquisitions, helping to shape Enstar’s international success. In 1994, Paul joined a run-off business venture in Bermuda, which grew to form part of the Enstar Group. From 1985 – 1994, he served as Executive Vice President, Chief Operating Officer and Director of Belvedere Group/Caliban Group.

Demian Smith
Group Chief Executive Officer of StarStone

Demian was appointed Group Chief Executive Officer of StarStone in December 2016, to lead StarStone’s global business which operates across three main regions: US and Bermuda, Lloyd’s and the London market, and Continental Europe. He previously served as Chief Executive Officer of StarStone’s International Operations from 2014, overseeing Lloyd’s and the London market and Continental Europe operations. He joined the company in 2010 as Global Head of Marine. An Associate of the Chartered Insurance Institute, Demian holds an MBA from Edinburgh University Management School and a B Eng. (Hons) in Naval Architecture from the University of Strathclyde, Glasgow.

David Message
Group Chief Underwriting Officer of StarStone

David was appointed Chief Underwriting Officer of International business in 2014, having joined the company in 2009 as Global Head of Offshore Energy. David is also Active Underwriter of StarStone’s wholly-owned Lloyd’s Syndicate1301. He has over 25 years of experience in the Specialty insurance market, beginning his career in the late 1980’s at Willis. He quickly progressed and later moved into the Offshore Energy field with Hiscox. Prior to joining StarStone he was Global Head of Offshore Energy and Regional Head of Marine at XL, which he joined in 2000.



Alexandra Cliff
Group Chief Financial Officer of StarStone

Alex was appointed Group Chief Financial Officer in April 2018. She recently served as Finance Director for StarStone International since 2016, having previously been StarStone Group Head of Financial Planning and Analysis. Prior to joining the company in 2012, she held senior finance roles at Aspen Group and Arthur J Gallagher International having spent eight years with PwC in both London and Boston, USA. A chartered accountant, qualifying with the Institute of Chartered Accountants in England & Wales, she also has an MA in History from the University of Edinburgh.

Linc Trimble
Executive Vice President of StarStone US

Linc joined the company in March 2009 to lead StarStone’s US Casualty operations, later founding its eCommerce platform. Prior to joining the company, he launched and managed Statehouse Casualty Managers, one of The McGowan Companies, where he served as President. Linc has more than 30 years of insurance experience and began his career in 1986 with Chubb Corp, holding several management positions including Senior Vice President of Property & Casualty at Chubb Atlantic in Bermuda.

Mark Sioma
Senior Vice President, Head of Management & Professional Liability of StarStone US

Mark was appointed Senior Vice President, Head of Management & Professional Liability in 2013. He joined StarStone in October 2010 as part of its global risk management team. Prior to joining StarStone, he held various leadership positions in the MPL sector, including at AIG and Crum & Forster. Mark has more than 35 years of experience in insurance. His background includes oversight of MGA operations with extensive expertise in product and program development.

Press Contact

Jenna Kerr
t: +44 (0)203 206 8251
e: jenna.kerr@enstargroup.com