Changing the COBRA status quo. Rethinking severance.

Per EBRI, COBRA participants cost nearly 300% more than active workers. This costs companies thousands of dollars every year.

When’s offboarding solution replaces COBRA in a severance package and When’s AI-driven health insurance marketplace makes it easy for exiting employees to find affordable alternatives to COBRA. Is your company Ready for When?

A partner to HR providing your employees a better offboarding experience

A fixed dollar reimbursement benefit in severance packages instead of paying for COBRA. Giving employees the flexibility to choose the right plan.

Our AI-driven marketplace integrates with your HRIS system making it easy for employees to find affordable alternatives to COBRA.

A marketplace of ACA and private medical plans, providing all exiting employees the choices and support they need. Decreasing healthcare costs for employers.

Here's how it works



  • Integration – Easy and quick one-time integration into your HRIS system. No data files and no manual entry.
  • Workflows – Create workflows for each exit scenario with assignable tasks and deadlines.
  • Document Management – Build a library of common exit documents with dynamic variables to auto-populate with employee specific data.



  • Case Management – Create and manage trackable cases for every employee exit.
  • Compliance – Stay compliant with local or state requirements by assigning specific workflows, documents and severance packages to individual cases.
  • Tasks – Assign specific exit workflow tasks to team members with clear visibility into upcoming and overdue items.
  • Health Insurance – Replace paying for COBRA in severance packages with a reimbursable dollar amount When benefit.


Employee Experience

  • Personalized Experience – When’s employee portal where they can view exit documents, find health insurance, make reimbursement claims, and access to career resources.
  • COBRA Alternatives – An innovative AI-driven health insurance marketplace makes it easy to find and enroll in affordable health insurance options from the ACA, private and short-term medical plans.
  • Concierge – 24/7 bilingual call center with licensed agents to assist former employees with Medicare and health insurance plan questions.



  • Analytics – Management dashboard for visibility into all turnover at your company and the related effort and cost.
  • Cost Savings – Lower company healthcare costs and mitigate risk by reducing COBRA continuation expenses.
  • ROI Analysis – Take 5 minutes to fill out this form and learn how much your company can save by implementing When.

Tired of COBRA?

Change the status quo with When.

After a job loss, many employees can’t afford COBRA and don’t know their medical plan options.
With When, companies have a partner to help exiting employees find affordable health insurance alternatives to COBRA in between jobs.
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