
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 career transitions. The platform integrates with HRIS systems like Workday, ADP, Rippling, and Prism, offering AI-powered assistance for healthcare plan options, career support, and severance solutions. Key pillars include seamless integration, comprehensive support, robust security with SOC 2 certification and HIPAA compliance, and data-driven insights for process improvement. When aims to transform the departure experience into an opportunity to build loyalty and empower employees, making last impressions lasting ones. The company serves various industries including Technology, Healthcare, Professional Services, Higher Education, Manufacturing, and Retail & Hospitality.

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 career transitions. The platform integrates with HRIS systems like Workday, ADP, Rippling, and Prism, offering AI-powered assistance for healthcare plan options, career support, and severance solutions. Key pillars include seamless integration, comprehensive support, robust security with SOC 2 certification and HIPAA compliance, and data-driven insights for process improvement. When aims to transform the departure experience into an opportunity to build loyalty and empower employees, making last impressions lasting ones. The company serves various industries including Technology, Healthcare, Professional Services, Higher Education, Manufacturing, and Retail & Hospitality.
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).
HQ & size: Chicago area (listed Highwood/Chicago); employee range reported as 11–50.
Post-employment and life-event health coverage decisions, employee offboarding, COBRA alternatives, and workforce transitions.
2020
Insurtech / HR & employee benefits
$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.
“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).”