Will Cunningham

Will Cunningham is the Chief Operating Officer at FLYR, a travel technology company based in San Francisco, California. He assumed this operational leadership position in September 2024 after previously serving as a board member and early investor in the business since 2021. Prior to joining FLYR, Cunningham was a Principal at WestCap, where he directed investments across the financial, experience, and infrastructure technology sectors. During his tenure in venture capital, he led investments in StubHub and iCapital, while holding board or observer seats at Hopper, Addepar, and AppDirect. Earlier in his career, he worked as an investor at Tenex Capital Management and Westfield Capital Management after earning a Bachelor of Arts in Statistics from Harvard University. His professional background centers on combining strategic capital allocation with executive management to scale growth-stage technology enterprises.