Under the leadership of CEO Andy Hamilton, When, a Chicago-based AI-driven offboarding platform, offers a comprehensive AI-powered platform designed to assist employees through the challenges of post-employment transitions. The platform specifically supports individuals in need of health insurance options, 401(k) rollovers, financial guidance, and career assistance after leaving a job.

When provides two primary solutions: a technology platform and the When Benefit. The technology platform is a co-branded portal tailored to the needs of exiting employees, while the When Benefit offers a more affordable and flexible alternative to traditional COBRA subsidies. Additionally, the platform collaborates with various partners to provide a full range of transition support services, including 401(k) rollovers, career coaching, and résumé building.

A key feature of When’s platform is its AI-powered health insurance marketplace, which allows users to compare their current coverage with plans from partners such as Healthcare.gov, Covered California, Medicare, and private insurers. This comparison tool helps users assess the costs associated with COBRA and choose the most suitable alternative plan.

When’s platform integrates with over 220 HRIS (Human Resource Information Systems) platforms, ensuring a personalized and compassionate offboarding experience. The company also provides a bilingual nationwide call center and high-touch customer service to support exiting employees throughout their transition. The marketplace’s partner offerings cover all aspects of job transition, providing comprehensive assistance from financial planning to career development.

The company recently disclosed that it has successfully secured $4.6 million in its latest Seed funding round. The round was led by B Capital, with participation from TTV Capital, Joyance Partners, Alumni Ventures, Network Ventures, and Enfield Capital Partners. This funding, combined with a previous $2.4 million round, brings When’s total capital raised to $7 million.

The company plans to use this investment to enhance its platform’s AI capabilities, expand its post-employment marketplace offerings, and broaden its customer base.

With this latest funding, When is poised to further expand its services and continue offering robust support to employees during the critical post-employment phase.