Meet our team

Experience you can trust

At Prospector, we believe our most important asset is our team. We’re proud to say that our 14 team members have an average tenure of 13 years with the Firm. On the investment side, our three Portfolio Managers, four Analysts and one Trader have a combined 150 years of financial analysis experience. On the business side, our five operational professionals and Chief Compliance Officer have a combined 160 years of experience. Consistency in team, strategy, and process is crucial to success in today’s markets, and at Prospector it shows.

Our team doesn’t just include the great people in our office. Alignment of interests is critical to the way we’ve built our business and investment strategies. As an investor in a Prospector strategy, our limited partners are key members of the Prospector team.

Leadership Biographies


John Gillespie

Portfolio Manager/Analyst

Mr. Gillespie has been a portfolio manager or securities analyst for more than 30 years. Since 1997, Mr. Gillespie has served as the managing member of Prospector Partners, LLC. Mr. Gillespie also serves as the managing member of Prospector Partners Asset Management, LLC, an affiliate that is registered with the SEC as an investment advisor and that acts as the investment advisor to Prospector Funds, Inc., a registered investment company. Mr. Gillespie served as a Director of White Mountains Insurance Group from 1999 until 2015. In addition, from 2002 to 2005, Mr. Gillespie served as non-executive Deputy Chairman of White Mountains Insurance Group and Chairman and President of their investment advisory subsidiary. From 1986 until 1997, Mr. Gillespie was an employee of T. Rowe Price Associates, Inc. At the end of his tenure at T. Rowe Price, Mr. Gillespie’s responsibilities included the management of assets of institutional investors, mutual funds, and closed-end investment companies. From 1980 through 1984, Mr. Gillespie was a Senior Financial Analyst at Geico Corporation. Mr. Gillespie received a B.A. cum laude from Bates College in 1980 and a M.B.A from the Graduate School of Business at Stanford University in 1986. In addition, Mr. Gillespie serves as Director and Chairman of Prospector Funds, Inc., and is also on the Board of Trustees and Chairman of the Investment Committee of Bates College. Mr. Gillespie’s past directorships include: Montpelier Re, Symetra Financial, Main Street America, Folksamerica, HG Global, Esurance, Tranzact, and One Beacon Insurance Group.

Kevin O’Brien, CFA

Portfolio Manager/Analyst

Mr. O’Brien has been a portfolio manager or securities analyst for more than 25 years. Throughout his career, Mr. O’Brien has followed the financial services sector. In April 2003, Mr. O’Brien became a portfolio manager of the Investment Manager. Mr. O’Brien is also a portfolio manager of Prospector Partners Asset Management, LLC. In addition, from April 2003 to August 2005, Mr. O’Brien served as a Managing Director of White Mountains Advisors LLC. From April 1996 through April 2003, Mr. O’Brien was an employee of Neuberger Berman, where he began as an investment analyst (1996 – 1999), served as Vice President (1999 – 2001), and Managing Director (2001 – 2003). At the end of Mr. O’Brien’s tenure at Neuberger Berman, Mr. O’Brien’s responsibilities included the co-management of equity assets of institutional investors and mutual funds, including serving as co-manager of the Neuberger Berman Genesis Fund. Mr. O’Brien was responsible for following stocks in the financial services, consumer and technology sectors. From 1991 to 1996, Mr. O’Brien was an employee of Alex. Brown & Sons, where he was an analyst following the financial services industry. His coverage universe included property-casualty insurance, specialty finance, asset management, and diversified financial services. From 1986 to 1991, Mr. O’Brien analyzed investments and credit risks in the financial services industry. Mr. O’Brien received a B.S. magna cum laude from Central Connecticut State University in 1986. Additionally, Mr. O’Brien received a Chartered Financial Analyst designation in 1995.

Jason Kish, CPA, CFA

Portfolio Manager/Analyst

Mr. Kish became a portfolio manager in 2013 and has been with the Investment Manager since December 1997. Mr. Kish is also a portfolio manager of Prospector Partners Asset Management, LLC. He has been a portfolio manager or securities analyst for more than 20 years. He began as a junior analyst, covering all industries, eventually serving as the property-casualty analyst and became the Director of Research in 2010. From 1995 to 1997, Mr. Kish worked as an auditor at Coopers & Lybrand, LLP in Hartford, CT. Mr. Kish received a B.S.B.A. from Providence College in 1995. He received his Certified Public Accountant designation in 2000 and his Chartered Financial Analyst designation in 2004 .

Peter Perugini, CPA, CFA

Chief Financial Officer

Mr. Perugini is the Chief Financial Officer of the Investment Manager and has been with the firm since its inception in 1997. He is also the Chief Financial Officer of Prospector Partners Asset Management, LLC and serves as Treasurer of Prospector Funds, Inc. From 1993 to 1997 he worked as an auditor at Coopers & Lybrand, LLP in Hartford, CT. Mr. Perugini received a B.S. degree in Accounting from University of Connecticut in 1992. Mr. Perugini received his Certified Public Accounting designation in 1996 and his Chartered Financial Analyst designation in 2000.

Kim Just, CPA

Chief Compliance Officer

Ms. Just has been the Chief Compliance Officer of the Investment Manager since March 2006 and Prospector Partners Asset Management, LLC since 2007. She also serves as Chief Compliance Officer of Prospector Funds, Inc. From September 1997 through March 2006 she worked as an auditor at Whittlesey and Hadley, LP in Hartford, CT in the areas of financial services and non-profit organizations. From March 1995 through September 1997, Ms. Just served as Planning Officer at Southington Savings Bank. Prior to that, she worked as an auditor for Ernst and Young and eventually Coopers and Lybrand, LLP. Ms. Just received a B.S. degree in Accounting from Central Connecticut State University in 1990 and her Certified Public Accounting designation in 1994.

Team Structure

  • John Gillespie*

    Portfolio Manager/Analyst

  • Kevin O’Brien, CFA

    Portfolio Manager/Analyst

  • Jason Kish, CPA, CFA

    Portfolio Manager/Analyst

  • Operations

    • Peter Perugini, CPA, CFA

      Chief Financial Officer

    • Margo Labaty, CPA, CFA

      Controller

    • Mark Michna, CFA*

      Assistant Vice President

    • Stephen Sam, CPA*

      Tax Director

    • Daryl Hegi*

      Accountant

  • Research

    • Kevin Clougherty, CFA*

      Analyst

    • Steven Labbe, CFA

      Analyst

    • James Romanelli

      Analyst

    • Christopher Clark

      Analyst

  • Trading

    • David Wehrle, CMT

      Trader

    Compliance

    • Kim Just, CPA

      Chief Compliance Officer

    *Advanced Degree