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 14 years with the Firm. On the investment side, our three Portfolio Managers, three Analysts and one Trader have combined over 160 years of financial analysis experience. On the business side, our five operational professionals and Chief Compliance Officer have over 100 years of experience. Consistency in team, strategy, and process is crucial to success in today’s markets, and at Prospector it shows.

Leadership Biographies


John Gillespie

Managing Member

Mr. Gillespie is the Founder and Managing Member of Prospector Partners, LLC. He was 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 and portfolio manager from 1997 until 2021. 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. 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 the Chairman of the Board of Trustees 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 30 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 25 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 .

Steven R. Labbe, CFA

Portfolio Manager/Analyst

Mr. Labbe is a portfolio manager at the Investment Manager and has been a portfolio manager or securities analyst for more than 25 years. Mr. Labbe joined Prospector Partners, LLC, an affiliate of the Investment Manager, in March, 2012. He began as an analyst, covering the insurance industry and gradually increased his coverage to asset managers, exchanges, and brokers; he became a portfolio manager in July, 2020. From 1996 to 2012, Mr. Labbe was employed as an analyst with Langen McAlenney, a division of Janney Montgomery Scott, covering the insurance industry. Mr. Labbe received a B.S. degree in Mathematics, from Central Connecticut State University in December, 1995. He received his Chartered Financial Analyst designation in 2001.

Peter Perugini, CPA, CFA

CFO/CCO

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.

Team Structure

  • John Gillespie*

    Managing Member

  • Kevin O’Brien, CFA

    Portfolio Manager/Analyst

  • Jason Kish, CPA, CFA

    Portfolio Manager/Analyst

  • Steven R. Labbe, CFA

    Portfolio Manager/Analyst

  • Operations

    • Peter Perugini, CPA, CFA

      CFO/CCO

    • Margo Labaty, CPA, CFA

      Controller

    • Arman Ahmed*

      Investment Operations Associate

    • Daryl Hegi*

      Accountant

    • Jean Charles Michel

      Accountant

    • Rhiannon Peters

      Accountant

  • Research

    • Kevin Clougherty, CFA*

      Analyst

    • James Romanelli, CFA

      Analyst

    • Christopher Clark, CFA

      Analyst

  • Trading

    • David Wehrle, CMT

      Trader

    Compliance

    • Peter Perugini, CPA, CFA

      CFO/CCO

    *Advanced Degree