Bowhead Specialty Founder Stephen Sills Shares His Journey in Insurance from Executive Risk, Chubb, Darwin and Beyond
August 16, 2021

Stephen Sills founded and now leads Bowhead Specialty, which came to life in July of 2020. He is the former chairman and CEO of CapSpecialty and Professional Risk Management Services. He founded Darwin Professional Underwriters in 2003 and served as its chairman, president and CEO until 2008.

Prior to Bowhead, he founded Executive Risk, where he served as chief underwriting officer and chief executive officer. In April, Risk & Insurance Editor- in-Chief Dan Reynolds caught up with Mr. Sills to discuss his latest venture. What follows is a transcript of that interview, edited for clarity and length.

Risk & Insurance: Stephen you’ve had an impressive career, having founded a number of successful companies. Can you take us back a bit and tell us about your background in more detail?

Stephen Sills:

My insurance career started as an aviation underwriter at Stewart Smith Aviation in New York City, and from there was invited by Joe Barrett, the Chief D&O Underwriter at Stewart Smith, one of the deans in the D&O business, to work with him on the D&O side. After many years of working with Mr. Barrett I had the opportunity to found Executive Risk and be its Chief Underwriting Officer.

Executive Risk was a joint venture between Aetna and various private equity groups.

After several years of growing the organization we expanded into Errors & Omissions and Medical Malpractice.

After a decade of building, the Aetna and private equity investors thought it was time to take the company public.

Which we did at $12.00 a share. We remained independent until purchased by the Chubb for approximately $70 a share. We had grown to over 600 employees, many of whom had never worked in insurance prior to joining us.

After being retired from Chubb for a few years, I approached Weston Hicks of Alleghany about starting a new company. I had known Weston from when he had followed Executive Risk while the number one insurance analyst in the country.

Our paths crossed again when he became the CFO of Chubb. We conceptualized a way to start a new professional liability company, that company ultimately became Darwin. We built Darwin for three years and then we took it public at $16 a share.

Two years after that, Allied World purchased Darwin for $32 a share. Subsequent to the merger I retired, again. A few years into retirement I received a call from Weston asking if I wanted to get involved in the turnaround of Capital Insurance. Over the next six years we rebranded the company (CapSpecialty), improved the expense ratio and increased the diversity of products and I subsequently retired from CAP Specialty in 2019.

After a year of retirement, I started speaking to Matt Botein, one of the co-founders of Gallatin Point. We agreed that the professional liability marketplace was in need of a new, very high quality entrant. We approached American Family and created Bowhead.

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