When, a workforce transitions platform to reduce 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 revenue growth year over year, customers including Varsity Brands, Iowa State University, and West Monroe, and its partnership with isolved, When has proven itself as the leader in benefits for health coverage transitions, saving money for both employees and employers on their healthcare costs. 

“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 respectively, make them ideal partners to help When achieve its next phase of growth.” 

When was founded in 2020 after neighbors Andy Hamilton and Dan Wertheimer, former leaders at Expedia Group and Target, respectively, experienced layoffs and the steep cost of COBRA health insurance that followed. While other HR and benefits platforms focus on onboarding and ongoing benefits administration, When addresses one of the most overlooked and costly gaps of the employee lifecycle: healthcare transitions for employees, whether they’re departing, retiring early, or otherwise eligible for alternative coverage.  

“When brings clarity, compliance, and cost savings to a very human problem,” said Nicole Gunderson, Principal at ManchesterStory. ”By meeting employers where they already operate - through brokers and HR platforms, When’s distribution-first approach positions them to become critical infrastructure for modern benefits transitions, and we’re proud to partner as they scale a new standard for workforce transitions.”

“Employers are looking for solutions that compassionately support people through workforce transitions, while also delivering measurable ROI,” said Robert Garber, Managing Partner at 7wire Ventures. “We are excited to partner with When to continue building out a world-class, AI-powered platform that helps consumers pick the best healthcare options for their personal situation."

At a time when both employers and employees are facing increasing healthcare costs, When offers a better path forward. Their AI-powered marketplace gives eligible employees personalized guidance to find affordable coverage alternatives that work for them, while the When Benefit replaces expensive subsidies with targeted reimbursements toward those plans, saving costs for both individuals and companies. 

These offerings have proven valuable. Since launching in January 2024, When has seen:  

• 4.3x revenue growth YoY from 2024 to 2025
• 66% growth in When headcount since 2024 
• 6,200+ companies (customers) and 1 million+ eligible employee users to date 
• 75,000 transition events recorded in 2025 alone
• Up to 80% savings on COBRA-related claims for employers 
• 92% employee/user satisfaction and 98% overall satisfaction
• Significant employee savings: For one company, the employees using When saved an average of $226 on their premiums 

“Having gone through a layoff myself, I’ve witnessed how incredibly difficult and costly workforce transitions can be, for both the employee and their employers,” said Dan Wertheimer, Co-Founder and Chief Strategy Officer, When. “As the way we work continues to evolve, we're long overdue for better models of managing healthcare and benefits that truly support workers and their families, while being sustainable for businesses.”

When plans to use the funding to grow its team and expand its offering to support companies across a wider range of coverage transitions, such as career transitions, Medicare eligibility, and early retirements.