# When Insurance > Benefits transition platform for employers managing workforce changes ## At a glance | Field | Value | | --- | --- | | Category | Specialty Solutions | | Type | Solutions Provider | | Region | NA | | Headquarters | United States | | Founded | 2020 | | Stage | Growth | | Employees | 11-50 | | Funding | Series A | ## Overview When Insurance is a benefits transition platform for employers managing workforce changes, operating primarily in the group benefits and health insurance market. The company's SaaS product addresses the financial and operational burden of COBRA continuation coverage by routing departing employees toward ACA marketplace plans and other private health coverage alternatives. The platform combines an AI-driven benefits marketplace with licensed concierge advisors who guide employees through health coverage decisions during involuntary exits, voluntary departures, retirement, and other transition scenarios. Employer-side integrations with major HRIS systems allow benefits teams to embed the service into existing offboarding workflows. The Health Severance Benefit feature lets employers redirect severance dollars into a defined health budget that employees can apply toward new coverage, reducing ongoing COBRA liability. Founded in 2020, the company has grown to serve more than 6,200 employer clients. When Insurance has raised USD 15.2M across a seed round and a Series A, with backing from investors including ManchesterStory, 7wire Ventures, TTV Capital, and B Capital. Recent milestones include a board appointment and continued hiring activity consistent with its growth stage. ## Products & services ### AI\-Powered Benefits Marketplace The core platform evaluates each departing employee's coverage circumstances and surfaces suitable ACA marketplace and private health insurance alternatives to COBRA continuation. The recommendation engine is tailored to individual eligibility and budget. **Key features:** - AI\-driven plan matching for departing employees - Comparison of ACA marketplace options against COBRA costs - Guided enrollment support through the marketplace *Target users:* HR and benefits teams at mid\-market and enterprise employers; departing employees ### Concierge Advisor Support A team of licensed benefits advisors is available for one-on-one consultations covering benefit navigation, Medicare transition, and retirement-era health planning. The service supplements the self-service marketplace for employees with complex coverage needs. **Key features:** - One\-on\-one sessions with licensed advisors - Medicare and retirement transition guidance - Support for RIF, voluntary exit, and early retirement scenarios *Target users:* Departing employees requiring personalized benefits guidance ### Health Severance Benefit An employer-facing product that reallocates severance funds into a dedicated health benefits budget. Employees apply the budget toward marketplace coverage of their choosing, replacing employer-sponsored COBRA subsidies with a portable, employee-directed alternative. **Key features:** - Employer\-defined health benefit budget for departing staff - Employee\-directed spend toward ACA or private plans - Reduces employer COBRA liability by directing employees to alternative coverage *Target users:* HR leadership, benefits administrators, finance teams managing workforce reductions ## Category & focus - Subcategories: COBRA Management, Benefits Transition, Employee Offboarding Benefits - Insurance verticals: Health, Group Benefits - Target customers: Employers ## Notable customers - 6,200\+ employer clients across diverse industries ## Links - Website: - Directory profile: - Careers: - Linkedin: --- *Last updated: 2026\-05\-18*