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.