A Chicago startup that wants to make changing jobs a little easier closed on new funding this week.
Post-employment job support platform When closed a $4.6 million seed round on Thursday led by B Capital with participation from TTV Capital, Joyance Partners, Alumni Ventures, Network Ventures and Enfield Capital Partners. The new funding brings the startup's total funding to $7 million.
Powered by artificial intelligence, When pulls in health insurance plans from places like healthcare.gov so exiting employees can compare benefits among competing plans and pick the best option. The startup also helps with other aspects of job transition, including 401(k) rollovers, career coaching and resume building.
Andy Hamilton and Dan Wertheimer founded When to help find affordable health insurance alternatives to COBRA for those who have recently reentered the job market.
A successful entrepreneur, Hamilton previously built two software-as-a-service startups, one of which, ApartmentJet, was acquired by Expedia in 2018. That division was eventually shut down, and going through that off-boarding process firsthand led Hamilton to his next venture.
"The lack of support, lack of tech and tools, even at a great company like Expedia, was totally jarring," he said.
Hamilton would go on to team up with his neighbor Wertheimer, who had had an idea for years to create a new health insurance solution.
"Dan had gone through a layoff and knew exiting employees need a better solution," he said.
When — a fully licensed health insurance broker in all 50 states and the District of Columbia — aims to help employers give a better off-boarding experience to employees, whether it's voluntary or involuntary.
"Part of the challenge here is people in the U.S. don't know how to shop for health insurance. With our platform, we wanted to make it easy and take the stress and anxiety away," Hamilton said.
COBRA plans, for example, on average cost three times more than those for active employees, Hamilton said. When one of When's Chicago-based clients used the platform following a staffing cut, the employer saved $1.4 million and the exiting employees saved $225 per month on average in premiums.
When will use its new funding to expand its AI capabilities and post-employment marketplace as well as grow its customer base.
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