Gene Shkolnik is a seasoned technology executive and CTO with nearly a decade of senior leadership experience driving product and engineering teams at consumer and public-sector platforms. He currently leads Insurify's engineering and AI-driven product strategy, after transforming MBTA’s digital infrastructure as a founding Head of Engineering and co-founding CoachUp where he built web and native apps. Gene has a track record of scaling teams and systems through high-growth events—having led KAYAK’s engineering through IPO and acquisition—while emphasizing measurable results, user research, and performance optimization. Technically grounded from early principal engineering roles in real-time personalization and embedded vision systems, he blends hands-on architecture skills with product-first leadership. Based in Reading, MA, he brings an operator-founder perspective informed by executive education at Babson and a long-standing focus on marrying analytics with delightful user experiences. An often-overlooked strength is his experience performing technical due diligence for investors, giving him a keen sense for what makes startups technically and commercially viable.
9 years of coding experience
24 years of employment as a software developer
UMass Lowell
Computer Science, Computer Science at Moscow State Automobile and Road Technical Institute (State Technical University) (MADI)
Executive Education Graduate Certificate Program, Executive Education Graduate Certificate Program at Babson College
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