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When Insurance
When is a comprehensive post-employment platform that streamlines offboarding, reduces COBRA costs by up to 70%, and equips exiting employees with tailored resources for healthcare, finances, and…
When Insurance
When is a comprehensive post-employment platform that streamlines offboarding, reduces COBRA costs by up to 70%, and equips exiting employees with tailored resources for healthcare, finances, and…
TL;DR
What they do: AI-powered workforce transitions platform that helps departing employees find COBRA alternatives via a health insurance marketplace and licensed-concierge support.
Signature offering: The When Benefit® — an employer-funded reimbursement that pays exiting employees' new plan premiums as a COBRA alternative.
Latest funding: Series A $10.2M announced Jan 30, 2026 (co-led by ManchesterStory and 7wire Ventures).
Earlier reported round: Dealroom lists an Aug 2024 Seed round of $4.6M (investors shown on Dealroom).
Chicago area (listed Highwood/Chicago); employee range reported as 11–50.
Company Overview
Problem Domain
Post-employment and life-event health coverage decisions, employee offboarding, COBRA alternatives, and workforce transitions.
Founded
2020
Industry
Insurtech / HR & employee benefits
Tech Stack
Funding Track Record
$4.6M
Dealroom lists an Aug 2024 Seed round of $4.6M with investors shown on the Dealroom profile.
Crunchbase lists a Seed round with BrokerTech Ventures as lead investor; amount/date not visible on accessed page.
$10.2M
Company announcement names ManchesterStory and 7wire Ventures as co-leads and lists participation from Mairs & Power Venture Capital and existing investors.
Investor Signal
“Series A co-led by ManchesterStory and 7wire Ventures; other named investors include Mairs & Power Venture Capital, B Capital, Enfield Capital Partners, TTV Capital, Alumni Ventures, BrokerTech Ventures, and investors listed on Dealroom (Joyance Partners, TTV Capital, B Capital Group, Network Ventures, Alumni Ventures).”
Founders
What we do
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