CHICAGO — When, the AI-powered offboarding solution designed to help employees navigate post-employment transitions and maintain access to healthcare by offering more affordable alternatives to COBRA, today announced it has closed its latest Seed funding round of $4.6 million led by B Capital and joined by TTV Capital, Joyance Partners, Alumni Ventures, Network Ventures, and Enfield Capital Partners.
This new infusion of capital, combined with When’s initial $2.4 million round, brings the company’s total amount raised to $7 million. When will use this funding to expand its platform’s AI capabilities, add new offerings to its post-employment marketplace, and grow its customer base.
When is reimagining the often-neglected post-employment experience through two distinct solutions: the When technology platform, a co-branded portal specifically designed to meet the needs of exiting employees, and the When Benefit, a healthcare severance solution replacing expensive, inflexible COBRA subsidies. Since COBRA participants are three times more costly than active employees, When enables employers to reduce health insurance costs and mitigate risk while providing employees with access to affordable coverage. In particular, When offers significant savings for companies that need to maintain health insurance for employees who retire early and are not eligible for Medicare. When’s solution also includes partner offerings for all aspects of the job transition, including 401(k) rollovers, career coaching, and résumé building.
“Unfortunately, many of us have had the universal experience of losing a job and suddenly facing the steep costs of COBRA coverage. Out-of-pocket health insurance costs and confusion around finding coverage are all too common problems for American workers, but they don’t need to be,” said Andy Hamilton, Co-Founder and CEO of When. “We founded When to remove the obstacles created by job loss, not add to them the way COBRA does. Our platform eliminates the stress of post-employment healthcare and creates an opportunity for seamless coverage while helping employers lower costs and mitigate risk. We are grateful for our investors’ vote of confidence as we make When the offboarding standard for U.S. employers.”
When’s AI-powered health insurance marketplace allows users to compare their current coverage with plans from partners including Healthcare.gov and Covered California, as well as Medicare and private providers, so they can understand the cost associated with COBRA and choose the plan that is best for them. Transitioning employees can apply their When Benefit to one of the available plans; on average, companies that offer When’s fixed-dollar health insurance premium reimbursement have seen an 80% conversion rate from COBRA, and employees have saved as much as 50% in out-of-pocket healthcare costs.
“B Capital has been a partner to When since Day 1, and we continue to be impressed by the When team’s vision and ability to innovate the offboarding process,” said Gabe Greenbaum, General Partner at B Capital. “The company is well positioned as an affordable, much-needed alternative to COBRA for employers across the country. We look forward to seeing When further enhance its suite of post-employment resources.”
Reductions in company headcount impact hundreds of thousands of Americans each year. US-based employers planned 721,677 job cuts in 2023, a 98% increase from 2022. With the exception of 2020, layoffs in 2023 reached the highest annual total since 2009, according to The Challenger Report. Yet despite the volume of impacted employees, the offboarding process has remained largely unchanged, and employees often have little support to navigate the complexities of maintaining healthcare coverage, rolling over a 401(k), and finding a new job during an incredibly stressful time.
“Some of our most successful portfolio companies were started by founders who wanted to solve a problem that they encountered firsthand. When is a great example of that – repeat entrepreneurs who have built an easier, more accessible way to maintain health insurance after a change in employment status,” said Lizzie Guynn, Partner at TTV Capital. “When is reimagining the entire offboarding experience in a way that makes economic sense for employers and employees alike, proving that we don’t have to accept the status quo. We’re proud to support them in the next phase of their growth.”
When’s technology platform seamlessly integrates with 220+ HRIS platforms to provide personalized and compassionate support during the offboarding process. Exiting employees have access to a bilingual nationwide call center and white-glove customer service. When’s marketplace includes partner offerings for all aspects of the job transition, from 401(k) rollovers to career coaching, résumé building, and more. To learn more about When’s solutions, visit https://www.forwhen.com.
About When
When is the AI-powered post-employment platform built for workers in between jobs who need support with health insurance, 401(k) rollovers, financial assistance, and career guidance. Employers that use When mitigate health insurance risks and costs by replacing expensive and inflexible COBRA subsidies with fixed-dollar health insurance premium reimbursements. Exiting employees can apply their benefit to plans on When’s health insurance marketplace, saving as much as 50% compared to COBRA. For more information, please visit https://www.forwhen.com.
