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.

How much can When save your company?

Number of Employees
Months of COBRA Severance
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Potential Savings


Avoided Claims:


Time Saved:


You can request a specific ROI analysis for your company

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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