Why We Invested in When

It’s one thing to recognize a problem that needs fixing. It’s another thing entirely to build an elegant solution that is also more cost-effective than the status quo. It’s not a simple task, even though it may be long overdue.

After Andy Hamilton was impacted by his company’s layoffs during the pandemic, he received a COBRA letter in the mail. He needed to figure out healthcare – and fast – but the process was stressful and antiquated. Like the tens of thousands of Americans who are laid off each year, Andy had sticker shock at the steep out-of-pocket costs associated with COBRA and thought, “Is this really my only option? Why isn’t there a better solution?” 

While most of us grumpily accept the status quo, Andy thought he could do something about it. He teamed up with his friend Dan Wertheimer, and the two founded When to actively solve this problem. When is an AI-powered offboarding platform designed to help employees maintain access to healthcare by providing more affordable alternatives to COBRA. Employers can sign up for the When technology platform, a co-branded portal specifically designed to meet the needs of exiting employees, and offer the When Benefit, a healthcare severance solution replacing expensive, inflexible COBRA subsidies. When is also building out its suite of partner offerings to support employees through their job transition, with resources ranging from 401(k) rollover support to career coaching and résumé building. 

Perhaps most impressive is how When is using AI to add real value for transitioning employees. When integrates with a company’s technology platform to securely gather insurance information from the employer. Employees can then chat with Jamie, When’s AI assistant, to learn about available health insurance plans based on their needs and previous coverage. In just a few minutes, Jamie surfaces options and presents them side-by-side so employees can easily compare pricing and deductibles from new plans with the insurance they had while employed. 

As we decide whether to invest in a company, we ask ourselves a number of questions: Are the founders experienced? Is there an opportunity to be a category creator? Is there a solid product-market fit? Is this company’s early traction an indicator of an unmet need? Will their use of technology enable them to scale meaningfully?

In When’s case, we’ve said “yes” to all of these. The company is led by repeat entrepreneurs who have a vision to reimagine the entire offboarding experience – a part of the employee lifecycle that is often neglected. While most companies have a robust onboarding process to acclimate new hires and set them up for success, offboarding is viewed as an afterthought. But we all know that last impressions are lasting, and that when companies treat their former employees with dignity, it benefits everyone.

The market opportunity for When is consequential, both in terms of size and timing. There are more than 700,000 companies in the United States with 20+ employees, which means they are required by law to offer COBRA. Further, last year’s 721,677 planned job cuts brought some of the largest reductions in company headcount that we’ve seen in the past two decades. Per The Challenger Report, layoffs in 2023 reached the second-highest annual total since 2009.

Offering an alternative to expensive, inflexible COBRA not only makes common sense but also economic sense. COBRA participants are three times more costly than active employees, which is especially burdensome for self-insured companies. When enables employers to reduce health insurance costs and mitigate risk of high claims while providing employees with access to affordable coverage. To date, companies that offer When’s fixed-dollar health insurance premium reimbursement have seen an 80% conversion rate from COBRA. And employees that applied their When Benefit to available plans have saved as much as 50% in out-of-pocket healthcare costs. The data couldn’t be more clear that When is a cost-effective, scalable solution.

We’re ready to support When as they enter the next phase of their growth. The company plans to use this funding to expand their AI capabilities and bring new customers onto the platform, and we believe that their product will alleviate the offboarding pain points and risks that are felt across industries. And as my team here at TTV looks to deploy more capital in the insurtech space, we know that finding the next company transforming an overlooked sector is not a matter of if, but When.