Leadership shake-up at Enstar as 28-year veteran to retire from top post

Re/insurance group  Enstar has suffled its leadership deck following the news that its longtime executive and group president Paul O’Shea (pictured) has decided to retire in March next year after serving the Bermuda-based legacy specialist and its predecessor Castlewood for more than 28 years.

O’Shea will remain as a member of the board of directors of  Enstar, and the group.

David Ni, who has worked with O’Shea since the start, will lead the company’s M&A activity going forward. Ni joined  Enstar in 2019 as EVP, M&A and was appointed chief strategy officer in May 2022.

The company's acting chief financial officer (CFO) and chief operating officer (COO) Orla Gregory will now transition full-time to the CFO role. She will continue to work closely with deputy CFO and chief accounting officer Mike Murphy and group treasurer Matt Kirk.

Gregory’s responsibilities as COO will be divided between chief claims officer Paul Brockman and chief of business operations Laurence Plumb.

Dominic Silvester,  Enstar's chief executive officer, said: “One of the best decisions in my career was asking Paul to join me at Castlewood Limited back in 1994. We have worked together through the many challenges of growing  Enstar, from a niche start-up into the leading global run-off specialist it is today. Paul’s ability to focus on delivering solutions together with his skill and dedication has been an essential part of successfully completing 113 run-off deals and acquiring more than $42 billion in insurance and reinsurance assets since formation. At the same time, Paul has helped to build a strong leadership team to ensure  Enstar can continue to deliver successful outcomes from our future pipeline of opportunities.

“On behalf of myself, the Board of Directors, and our 830-plus employees, I thank Paul for his dedication and support. We are delighted that he will remain with us as a director and wish him much happiness in his well-deserved retirement.”

O’Shea added: “ Enstar's success over the past 28 years is a result of the hard work and commitment of so many, too many to acknowledge here. However, I thank Dominic for inviting me to join his team back in 1994 and for all his guidance and support over the years.  Enstar is a very special company, and it’s been a privilege to work with such exceptional talent as we developed beyond what any of us could have imagined. The corporate ethos and dedication of each employee will continue to generate success into the future. I look forward to continuing my association with  Enstar as a director.”

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