benefits-platform
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Guy Benjamin
Guy Benjamin is the CEO and co-founder of Healthee, a New York-based company that uses AI to help employees understand and use their health benefits. A former Israeli Air Force fighter pilot with a Yale MBA and a McKinsey background, he started Healthee in 2021 after struggling to navigate his own employer benefits in the US. The company has grown past 15,000 customers, counts Instacart, SiriusXM, and Celonis among its clients, and has raised $111 million in total funding, including a $50 million Series B in 2025.
Justin Holland
Justin Holland is the co-founder and CEO of HealthJoy, a Chicago-based digital health company that turns the maze of employee benefits into a single AI-guided app. An MIT-trained engineer and serial entrepreneur with two prior exits (OpenInstall to AVG/Avast and FreeCause to Rakuten), he started HealthJoy in 2014 after a personal run-in with the American healthcare system left him unable to find out what his own care would cost. He has led the company for more than a decade, raised roughly $108M in venture financing through a Series D, and built a platform now used by hundreds of thousands of members to navigate care, cut costs, and reach a virtual assistant named JOY.
Anirban Gangopadhyay
Anirban Gangopadhyay is the co-founder and CTO of Angle Health, an AI-native health insurance platform serving small and mid-sized businesses across 44 U.S. states. A Columbia University computer scientist and former Palantir machine learning engineer, he previously served as a Stokes Scholar at the U.S. Department of Defense and co-founded Zircon Technologies - an AI-enabled clinical trial recruitment startup that was acquired - before building Angle Health through Y Combinator's W20 batch. Angle Health raised $134 million in a December 2025 Series B and has grown revenue 26x since its Series A, with a mission to redesign healthcare delivery through AI-first technology.