When Insurance

Benefits transition platform for employers managing workforce changes

Specialty Solutions Growth 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

At a Glance

Founded: 2020
Headquarters: United States
Employees: 11-50
Funding: Series A

Category & Focus

Category: Specialty Solutions
Subcategories: COBRA Management Benefits Transition Employee Offboarding Benefits
Insurance Verticals: Health Group Benefits
Target Customers: Employers