Overview
Gillette holds a Bachelor's Degree in Economics and History from Boston College, earned between 1988 and 1992[11]. Gillette serves as Board Observer at Stratyfy as of February 2023[1][4] and as CFO and Co-Founder of Fox Ridge Capital beginning February 2026[3]. Throughout Gillette's career, the professional has built and transformed lending businesses, twice growing lending operations from near-zero to over $1 billion[2]. Prior roles include Senior Vice President of Fintech Partnerships, Solar and Specialty Lending at NBT Bank from November 2015 to August 2025[8], Head of Digital Lending at Grasshopper Bank from February 2025 to March 2026[7], and Senior Advisor at Gordon Brothers from June 2024 to April 2026[6]. Gillette also served as Chair of the Board of Trustees at Punchard Trustees from March 2022 to March 2025[10] and as Funding Partner at Lawrence Dream Network from July 2020 to June 2025[9].
Profile introduction
Working with great teams, I build and transform scalable, profitable lending businesses - twice growing lending businesses from near-zero to over $1B. I'm now CFO of Fox Ridge Capital & working with the incredible Fox Ridge team to reimagine business financing. Throughout my career, I’ve worked with industry leaders to launch innovative products, including NBT Bank's national solar lending program and the first fully digital secured financing process at Direct Capital, both of which were recognized for their industry-leading capabilities. A trusted advisor and board member, I’ve worked w…
Career history
- CFO & Co-FounderFeb 2026 to presentFox Ridge Capital
- Board ObserverFeb 2023 to presentStratyfy
- MemberSep 2022 to presentChief
- Senior AdvisorJun 2024 to Apr 2026Gordon Brothers
- Head of Digital LendingFeb 2025 to Mar 2026Grasshopper Bank
- Senior Vice President, Fintech Partnerships, Solar and Specialty LendingNov 2015 to Aug 2025NBT Bank
- Funding PartnerJul 2020 to Jun 2025Lawrence Dream Network
- Chair of the Board of TrusteesMar 2022 to Mar 2025Punchard Trustees
Education
Bachelor’s Degree, Economics & History1988 - 1992Boston College
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