Today, When announced a $10.2M Series A funding round, co-led by ManchesterStory and 7wire Ventures, with participation from Mairs & Power Venture Capital and existing investors B Capital, Enfield Capital Partners, TTV Capital, and Alumni Ventures.

Read the full coverage in Axios and the official press release in EIN Presswire.

The funding comes on the heels of 4.3x revenue growth YoY, with 6,200+ companies now using When and over 1 million employees having access to the platform.

The timing couldn't be more critical as healthcare costs continue their relentless climb and employers face mounting pressure to control benefits spending. That's exactly where When comes in: a rare solution that reduces costs while improving the employee experience.

We're thrilled to have ManchesterStory and 7wire backing us. Their experience in health insurance and health tech will be invaluable as we grow.

Why Now, Why This Team

The investor lineup reflects When's dual mandate: solve a human problem while delivering measurable business outcomes.

ManchesterStory, backed by $250 million in committed capital from insurance carriers and brokers, brings deep distribution expertise and industry relationships that will accelerate When's reach across the benefits ecosystem.

7wire Ventures, the leading consumer digital health venture capital firm, brings proven experience scaling health tech platforms that empower consumers to make better healthcare decisions.

The results validate what When’s building: 

• 92% employee satisfaction

• 75,000 transition events in 2025

• Up to 80% savings on COBRA-related claims for employers.

• Growing traction with Fortune 500 companies

Building the Future of Workforce Transitions

This funding accelerates When's expansion into a comprehensive workforce transitions solution. The company is building infrastructure to support employees and their dependents across multiple life events: early retirements, Medicare eligibility, career pivots, and portable health benefits. 

The vision extends beyond single-point solutions. When is positioning itself as the platform that supports employees whenever their circumstances require them to change to their coverage, creating a continuous relationship throughout the employment lifecycle, not just at exit.

As Robert Garber, Managing Partner at 7wire Ventures, put it:

"Employers are looking for solutions that compassionately support people through workforce transitions, while also delivering measurable ROI. 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."

For CFOs and benefits leaders navigating 2026's economic uncertainty, When represents a controllable cost lever in an otherwise unpredictable benefits landscape. The platform delivers immediate financial impact while strengthening the employer brand. A combination that's increasingly rare in the benefits/health insurance technology space.

A New Standard for Employer-Employee Relationships

When's success reflects a broader shift in how forward-thinking companies view their responsibilities. The way an organization treats departing employees isn't just an HR checkbox, it’s a statement about values that current employees notice and prospective employees research.

But the business case is equally compelling. Companies using When aren't just building better reputations, they're reducing measurable financial risk. In an environment where every benefits dollar faces scrutiny, When offers a rare win-win: lower costs, better outcomes, stronger employer brand.

For self-insured employers especially, the financial volatility of healthcare costs makes When's value proposition increasingly urgent. Every COBRA participant represents potential six-figure claims exposure. When helps employers manage that risk proactively rather than reactively.

The Path Forward

"We're long overdue for better models of managing healthcare and benefits that truly support workers and their families, while being sustainable for businesses."

- Dan Wertheimer, Co-Founder and Chief Strategy Officer

The Series A positions When to become that better model. Not just for one type of transition, but for the fundamental vulnerability in a system where health insurance is tied to employment, yet employment itself has become increasingly fluid.

As work continues to evolve with more contract roles, more career pivots, more layoffs, more early retirements, more workforce mobility, the need for seamless coverage transitions will only grow. So will the financial imperative to manage these transitions efficiently.

When is building the infrastructure to support that future, where companies can navigate workforce changes without choosing between treating people well and protecting their bottom line.

To the companies that partner with When: thank you for believing that supporting people and managing costs aren't mutually exclusive, they're complementary.

To the employees navigating transitions with When: you deserve support during vulnerable moments, not just paperwork and panic.

How you say goodbye matters just as much as how you say hello. With this funding, When is ensuring more companies can say goodbye the right way, while protecting their financial health in an increasingly volatile healthcare landscape.