Chicago’s When raises $10.2M to expand health coverage platform

When, a startup that helps employees navigate health insurance after job changes, announced last week it has raised $10.2 million in a Series A financing round as it seeks to broaden its services and grow its customer base.

The round was co-led by ManchesterStory, an investment firm based in Des Moines, Iowa and Chicago venture firm 7wire Ventures, with participation from Mairs & Power Venture Capital in Minneapolis and existing backers including B Capital, Enfield Capital Partners, TTV Capital and Alumni Ventures. The company said it will use the new capital to hire more staff and extend its product to cover additional types of coverage transitions such as career moves, Medicare eligibility and early retirements.

When was founded in 2020 by Andy Hamilton and Dan Wertheimer, former executives at Expedia Group and Target respectively, after they experienced their own layoffs and the high cost of continuing COBRA coverage. The company launched its platform publicly in January 2024 and positions itself as a “workforce transitions” service that guides employees through the often-complex choices they face when they lose or change employer-sponsored health coverage.

The company’s offering combines an AI-driven marketplace for personalized coverage options with what it calls the When Benefit, a targeted reimbursement mechanism intended to offset employees’ out-of-pocket costs for alternative plans. When says this approach can reduce employer COBRA-related claims costs and lower premiums for individuals.

When provided performance figures as part of the announcement: 4.3x year-over-year revenue growth from 2024 to 2025, more than 6,000 corporate customers and over 1 million eligible employees on the platform, 75,000 transition events recorded in 2025, and up to 80% savings on COBRA-related claims for employers in some cases. The company also reported high user satisfaction scores, stating 92% employee/user satisfaction and 98% overall satisfaction.

Investors emphasized the market need with Nicole Gunderson of ManchesterStory highlighting the company’s distribution through brokers and HR platforms, while 7wire’s Robert Garber pointed to “measurable ROI” and said that When is building an “AI-powered platform that helps consumers pick the best healthcare options for their personal situation.”

COBRA, the federal law that allows some employees to continue employer-based coverage after a qualifying event, can be expensive, and navigating alternatives such as marketplace plans, spouse coverage, Medicaid or short-term policies can be confusing for workers in transition.

When’s model targets that decision point, working with employers, brokers and HR platforms to surface options and administer reimbursements where applicable. The company also highlighted a partnership with payroll and HR provider isolved as part of its go-to-market approach.

Still, the space is competitive and regulatory complexity around subsidies, plan eligibility and state Medicaid rules can complicate implementation at scale.

When joins a cohort of benefit-focused startups trying to modernize parts of the employee lifecycle that traditional HR systems often overlook. With fresh capital, the company plans to accelerate product development and expand its customer reach as employers continue to look for ways to manage benefits during economic uncertainty and workforce churn.

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