When, founded by Andy Hamilton and Dan Wertheimer and based in Chicago, offers a software platform that guides organizations and their employees through healthcare and benefits changes triggered by events such as early retirements, career pivots, involuntary exits, Medicare eligibility, and other coverage transitions. The solution aims to reduce employer costs while delivering personalized support to transitioning workers. Since its launch in 2024, more than 6,000 companies have adopted the platform, giving over 1 million employees access to its tools. Current functionality centers on simplifying benefits navigation, but the company plans to broaden its coverage to additional transition scenarios, including Medicare and early retirement pathways. Proceeds from its recent Series A will be used to expand the team and enhance product capabilities to serve a wider array of workforce transitions. The company’s traction across thousands of employers demonstrates early product-market fit and provides a growing revenue base, although specific revenue figures were not disclosed.

Total raised

$15M

Funding rounds

2

Latest round

Series A

Latest activity

Feb 2026