When, a workforce transitions platform focused on reducing healthcare costs, today announced it has raised $10.2 million in Series A funding. The round was co-led by Des Moines-based ManchesterStory and Chicago-based 7wire, with participation from new investor Mairs & Power Venture Capital and existing investors B Capital, Enfield Capital Partners, TTV Capital, and Alumni Ventures.

With 4x year-over-year revenue growth, customers including Varsity Brands, Iowa State University, and West Monroe, and a strategic partnership with isolved, When has established itself as a leader in benefits for healthcare coverage transitions—helping both employees and employers significantly reduce healthcare expenses.

“We couldn’t be more grateful to have the support of investors like ManchesterStory and 7wire on our side,” said Andy Hamilton, Co-Founder and CEO of When. “Their expertise in health insurance and health tech make them ideal partners to help When achieve its next phase of growth.”

Solving an Overlooked Gap in the Employee Lifecycle

Founded in 2020 by neighbors Andy Hamilton and Dan Wertheimer—former leaders at Expedia Group and Target—When was born out of firsthand experience with layoffs and the high cost of COBRA health insurance.

While many HR and benefits platforms focus on onboarding and ongoing benefits administration, When addresses one of the most overlooked and expensive moments in the employee lifecycle: healthcare transitions. This includes layoffs, early retirement, and other situations where employees become eligible for alternative coverage.

“When brings clarity, compliance, and cost savings to a very human problem,” said Nicole Gunderson, Principal at ManchesterStory. “Their distribution-first approach positions them to become critical infrastructure for modern benefits transitions.”

AI-Powered Guidance with Measurable ROI

As healthcare costs continue to rise for both employers and employees, When offers an AI-powered marketplace that provides eligible employees with personalised guidance to find affordable healthcare alternatives.

In addition, the When Benefit replaces costly subsidies with targeted reimbursements toward alternative plans—delivering savings for companies while supporting employee wellbeing.

“Employers are looking for solutions that compassionately support people through workforce transitions while delivering measurable ROI,” said Robert Garber, Managing Partner at 7wire Ventures.

Strong Momentum Since Launch

Since launching in January 2024, When has demonstrated strong traction and impact:

• 3x revenue growth year over year from 2024 to 2025
• 66% growth in headcount since 2024
• 6,200+ companies served and 1M+ eligible employee users
• 75,000 transition events recorded in 2025 alone
• Up to 80% savings on COBRA-related claims for employers
• 92% employee satisfaction and 98% overall satisfaction
• Average employee premium savings of $226 at one customer organisation

“Having gone through a layoff myself, I’ve witnessed how incredibly difficult and costly workforce transitions can be,” said Dan Wertheimer, Co-Founder and Chief Strategy Officer. “We’re long overdue for better models that truly support workers and families while remaining sustainable for businesses.”

What’s Next for When

When plans to use the new funding to expand its team and broaden its platform to support a wider range of coverage transitions, including career changes, Medicare eligibility, and early retirement scenarios.