Winslow named CFC CEO as O’Shea steps down

Winslow will join the specialist insurer later this summer, subject to regulatory approval.

In the meantime, group capacity director Andy Holmes will serve as acting CEO.

The appointment comes after Winslow led Direct Line Group through its £3.7bn sale to his former employer Aviva.

On behalf of the board and everyone in the business, I want to thank Louise for her significant contribution to CFC and the progress made under her leadership. I look forward to working with Adam.

John Howard, CFC

Before stepping in to take the top job at Direct Line Group, and try to turn around the insurer’s fortunes, Winslow had previously run Aviva’s UK and Ireland general insurance business, with CFC’s chief financial officer Jane Poole as his right-hand woman.

When he jumped Aviva’s ship for Direct Line, Poole was one of his first major appointments.

After Aviva bought Direct Line, both Winslow and Poole exited. Poole joined CFC as CFO in September 2025.

CFC chairman John Howard said Winslow’s appointment comes at “an exciting time” for the specialist insurer as it seeks to accelerate global growth while unlocking the potential of artificial intelligence across its operations.

He added Winslow’s experience of driving profitable growth and operational execution would support the firm’s next phase of international expansion and AI-enabled innovation.

“Adam brings more than 20 years of leadership experience and a strong track record of delivering results in both public and private environments,” Howard said.

“On behalf of the board and everyone in the business, I want to thank Louise for her significant contribution to CFC and the progress made under her leadership.

“I look forward to working with Adam to build on the momentum that Louise and the team have achieved.”

Winslow succeeds O’Shea, who has led CFC for almost six years, having first joined the business as an independent non-executive director before becoming CEO.

While she is stepping down from the role with immediate effect, CFC confirmed she remains a significant shareholder in the business.

Winslow said: “CFC is one of the genuine success stories of the specialty market - a business with a distinctive model, an exceptional team and real momentum. That’s what attracted me, and it’s why I’m delighted to be joining.

“My thanks go to Louise for a warm handover and to John and the board for the opportunity to lead CFC into its next phase of growth. I can’t wait to get started.”

O’Shea said it had been “an absolute privilege” to lead the business and expressed confidence that Winslow was the right leader for CFC’s next stage of development and international expansion.

Friends reunited

The move comes less than a week since Insurance Post content director Jonathan Swift speculated that Winslow could be heading to CFC.

Swift noted that Poole had already made the move to the specialist insurer and questioned whether Winslow could this time follow her lead.

Swift also suggested the timing reflected wider consolidation in the specialty market following Zurich’s acquisition of Beazley and ongoing market speculation around Hiscox, including a possible approach from Intact, that Post first reported in May.