Olive AI

How it happened

Olive AI built automation software for healthcare administrative workflows and raised about $852M, reaching a ~$4B valuation in 2021. The company struggled to deliver promised efficiencies, narrowed its focus, and ran short of capital. Employee reviews were blunter: insiders described the "AI" as brittle automation running at roughly 30% effectiveness, sold faster than it could be built, with the delivery teams absorbing the gap. The July 2022 layoff — about 450 people, a third of the company — arrived by mass Slack message with laptops locked within minutes, days after leadership assured staff there would be no cuts. After selling off business lines, it shut down in late 2023, a near-total loss.

Employee accounts paraphrase anonymous, unverified reviews posted publicly on Glassdoor ↗. See our methodology.