The Birth of When

The idea of When began during the Great Recession of 2008.

Dan Wertheimer proposed the idea for a business school project at the Booth School of Business at the University of Chicago. He’d seen the realities of COBRA, the cost of continuation coverage, and the impact it had on people and families after a job loss.

At the time, Dan didn’t have a team to make the idea a reality. He also thought upcoming health care reform under the Obama Administration might render the idea redundant.

Unfortunately, the Affordable Care Act didn’t directly address the problem of continuation coverage after a job loss.

Fast forward twelve years. Dan’s neighbor, Andy Hamilton, had recently sold a business to Expedia Group, and the entire division was shut down during the COVID pandemic. Dan had been telling Andy about the idea for years, and now Andy was suddenly on COBRA. The cost of health insurance for Andy’s family had increased by over 700% after he lost his job. 

This reinforced the scope of the problem. Andy and Dan pulled in Kevin Koperski, a co-founder with Andy’s previous business, who was also on COBRA at the time, and, together with Patrick Koeller, they launched what would become When Insurance.

They wanted to make a difference. They wanted to help others prepare for the situations they had faced. But they had no insurance background.

Thus began a long journey of learning, networking, proposing, and revising. They built an advisory team of insurance industry specialists, heavy hitters in the HR and Benefits spaces, as well as people with legal and startup expertise. They built relationships with insurance carriers, brokers, and distribution partners. They worked with actuarial firms to design the insurance product, and they consulted with other InsureTech companies to understand the needs of platform users.

That long journey is nearly at its first major milestone. A 2023 launch. The team is finalizing policies and contracts, building out technology and support teams, and lining up pilot customers.

The goal is to bring a new sense of financial well being to every employee in America who buys health insurance through an employer.

Welcome to When. We hope you’ll come along for the ride.

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