The Bill That Started It All

In May 2020, Andy Hamilton's entire division at Expedia was shut down. Not trimmed. Shut down. The next month, his family's health insurance bill arrived: over $2,100, up from roughly $260. Same plan. Same coverage. The only thing that changed was his employment status.

His neighbor, Dan Wertheimer, knew the math. He'd lived it twelve years earlier during the Great Recession, when his premiums jumped from $50 to $800 a month after a layoff. Back then, Dan sketched out a solution as an MBA project at Chicago Booth, then shelved it, assuming healthcare reform would close the gap.

It didn't.

So when both neighbors found themselves laid off at the same time, comparing bills over the fence, the shelved idea came back. They decided to build what the system should have built already.

The Problem We Set Out to Solve

Employers subsidize most of your health insurance premium while you're employed. When the job ends, that subsidy vanishes. COBRA lets you keep the same plan, but now you pay 102% of the full cost. A family paying $500 a month suddenly owes $3,000.

The result: employees scramble, go uninsured, or make rushed decisions at the worst possible moment. And for employers, COBRA enrollees file claims at three times the rate of active employees, creating significant cost exposure on the way out.

What We Built

When Insurance launched in 2023 to change that math on both sides.

The platform analyzes each departing employee's situation and presents alternatives that actually fit: ACA marketplace plans, spouse coverage, short-term options, or COBRA when it genuinely makes sense. Licensed professionals provide real support around the clock.

For employees, it's guidance instead of paperwork and panic. For employers, it's measurable results: 80% of employees shift to better-fit plans, cutting COBRA-related claims costs by up to 80%. Client satisfaction sits at 92%.

Three years in, When serves over 6,200 companies and more than one million employees.

What's Next

This week, we raised $10.2M in Series A funding, co-led by ManchesterStory and 7wire Ventures, with participation from Mairs & Power Venture Capital and existing investors B Capital, TTV Capital, Enfield Capital Partners, and Alumni Ventures.

The investment accelerates our expansion beyond single-point solutions. We're building infrastructure to support employees across workforce transitions: early retirements, Medicare eligibility, career pivots, portable benefits. The goal is a continuous relationship throughout the employment lifecycle, not just at exit.

Why It Matters

The way a company treats departing employees says something. Current employees notice. Prospective employees research it. We're making it easier to get that moment right while protecting your bottom line.

In 2008, Dan saw the gap and assumed someone would close it. In 2020, Andy fell into it. Now they've raised the capital to scale the bridge.

Read the full Series A Press Release HERE.