The Workforce Transitions Platform
Redefining how employers manage life events
When is the AI workforce transitions platform that turns workforce change into savings. We lower high-cost medical claims, reduce COBRA liability, and protect your brand by delivering an exceptional employee experience for when it matters most.
The Workforce Transitions Platform
Redefining how employers manage life events
When is the AI workforce transitions platform that turns workforce change into savings. We lower high-cost medical claims, reduce COBRA liability, and protect your brand by delivering an exceptional employee experience for when it matters most.
The Workforce Transitions Platform
Redefining how employers manage life events
When is the AI workforce transitions platform that turns workforce change into savings. We lower high-cost medical claims, reduce COBRA liability, and protect your brand by delivering an exceptional employee experience for when it matters most.









Trusted by over 6,000 companies
Trusted by over 6,000 companies
Trusted by over 6,000 companies
The Problem We Solve
COBRA claims cost millions.
Bad exits damage brands.
High-profile RIFs and surging healthcare claims are exposing the hidden financial and reputational risks of employee transitions.
Annual U.S. transitions
60M+
Employee Life Events
COBRA Participants
300%
More Costly
Healthcare Costs
56%
Increase Over 4 Years
Annual U.S. transitions
60M+
Employee Life Events
COBRA Participants
300%
3X
More Costly
Healthcare Costs
56%
Increase Over 4 Years
The When Solution
A better outcome for everyone

Reduce Healthcare Costs & Risk
Reduce your financial risk by lowering high-cost COBRA claims. Our platform guides employees to affordable coverage, helping you control spend, improve your medical loss ratio, and shield your business from renewal increases.

Reduce Healthcare Costs & Risk
Reduce your financial risk by lowering high-cost COBRA claims. Our platform guides employees to affordable coverage, helping you control spend, improve your medical loss ratio, and shield your business from renewal increases.

Reduce Healthcare Costs & Risk
Reduce your financial risk by lowering high-cost COBRA claims. Our platform guides employees to affordable coverage, helping you control spend, improve your medical loss ratio, and shield your business from renewal increases.

Ensure Employee Well-being
Transform exits into a supportive experience that protects your brand. With live advisors and personalized guidance, employees can confidently navigate healthcare options, ensuring they feel supported long after their last day.

Ensure Employee Well-being
Transform exits into a supportive experience that protects your brand. With live advisors and personalized guidance, employees can confidently navigate healthcare options, ensuring they feel supported long after their last day.

Ensure Employee Well-being
Transform exits into a supportive experience that protects your brand. With live advisors and personalized guidance, employees can confidently navigate healthcare options, ensuring they feel supported long after their last day.

Simplify Complex Transitions
Streamline offboarding with an AI-powered platform that complements your existing COBRA process. It integrates with all major HRIS systems , creating a seamless, compliant, and low-effort experience for your entire HR team.

Simplify Complex Transitions
Streamline offboarding with an AI-powered platform that complements your existing COBRA process. It integrates with all major HRIS systems , creating a seamless, compliant, and low-effort experience for your entire HR team.

Simplify Complex Transitions
Streamline offboarding with an AI-powered platform that complements your existing COBRA process. It integrates with all major HRIS systems , creating a seamless, compliant, and low-effort experience for your entire HR team.
Guidance for When they need it most
Guidance for When
they need it most
From planned retirements to unexpected layoffs, every transition is unique. We provide tailored support for a wide range of scenarios to ensure no one is left without a clear path forward.

Involuntary Exits

Medicare Navigation

Voluntary Exits & COBRA

Early Retirement
Involuntary Exits
Medicare Navigation
Voluntary Exits & COBRA
Early Retirement
Involuntary Exits
Medicare Navigation
Voluntary Exits & COBRA
Early Retirement
92% Employee Satisfaction Rating
92% Employee Satisfaction Rating
92% Employee Satisfaction Rating
A fully integrated suite of transition benefits
Our AI-powered platform guides former employees to affordable COBRA alternatives, reducing costs while strengthening your employer brand and demonstrating lasting commitment to your people.
AI-Powered Marketplace
Offer the best-fit ACA & private plans
Empower a confident, informed choice
Provide smart COBRA alternatives
AI-Powered Marketplace
Offer the best-fit ACA & private plans
Empower a confident, informed choice
Provide smart COBRA alternatives
AI-Powered Marketplace
Offer the best-fit ACA & private plans
Empower a confident, informed choice
Provide smart COBRA alternatives
Concierge Advisor Support
Provide guidance from licensed advisors
Give them one-on-one support anytime
Navigate retirement & Medicare options
Concierge Advisor Support
Provide guidance from licensed advisors
Give them one-on-one support anytime
Navigate retirement & Medicare options
Concierge Advisor Support
Provide guidance from licensed advisors
Give them one-on-one support anytime
Navigate retirement & Medicare options
Health Severance Benefit
Redirect funds away from COBRA
Reduce your company's financial risk
Use as early retirement health benefit
Health Severance Benefit
Redirect funds away from COBRA
Reduce your company's financial risk
Use as early retirement health benefit
Health Severance Benefit
Redirect funds away from COBRA
Reduce your company's financial risk
Use as early retirement health benefit


The cost savings were significant, but the real victory is in the peace of mind we've provided our departing colleagues.
HR Executive
Actionable insights for HR leaders and advisors
"Employers are looking for new and creative ways to enhance their offerings to help attract and retain employees. Those who partner with When will stand out when competing for talent."
Tracy D
Head of Global Benefits & Wellbeing
"Employers are looking for new and creative ways to enhance their offerings to help attract and retain employees. Those who partner with When will stand out when competing for talent."
Tracy D
Head of Global Benefits & Wellbeing
"Employers are looking for new and creative ways to enhance their offerings to help attract and retain employees. Those who partner with When will stand out when competing for talent."
Tracy D
Head of Global Benefits & Wellbeing