When Joins the Workday Wellness Partner Ecosystem

CHICAGO, November 12, 2026 — When™, the enterprise platform for guided health insurance decisions at every qualifying life event, today announced it has joined the partner ecosystem for Workday Wellness, part of Workday Total Benefits.

COBRA was designed to address compliance, not to manage an employee's coverage transition. That leaves one of the most consequential moments in the employee lifecycle largely unmanaged. A twenty-page packet stands in for a decision nobody in the benefits ecosystem owns, and it produces the most expensive outcome for everyone involved. COBRA participants generate significantly higher claims than active employees. A 2025 Tokio Marine study found they were responsible for 15 times as many $1 million claims.

When™ Next is an integrated, decision support technology solution for employees losing employer-sponsored health insurance. Employees see plans available to them, priced against their COBRA cost and checked against their current doctors and prescriptions. Licensed, non-commissioned agents are available to answer any questions and fully enroll members in a new plan.

"COBRA solves a compliance obligation. It does not solve the coverage decision. Treating COBRA as the complete answer is like confusing tax filing with financial planning," said Andy Hamilton, Co-Founder and CEO of When™. "Benefits leaders recognize the gap. The challenge has always been the cost and complexity of adding another solution. By meeting employers inside Workday, we remove much of that friction and make managing coverage transitions far easier to adopt."

Workday Wellness is an AI-powered solution that revolutionizes employee benefits experiences by offering a real-time view into the benefits and wellness offerings employees use and value most. This partnership will deliver greater administrative efficiency for employers and provide actionable insights that maximize engagement with both employers and employees. Employers will gain powerful tools to measure effectiveness of their benefit offerings and dynamically adapt those benefits to better meet their employees' needs.

"Nothing changes for active employees, carriers, COBRA administrators, or the benefits team," said Tom Cox, VP of Commercial Partnerships at When™. "That has always been central to how we deploy. Being part of the Workday ecosystem simply gives employers greater confidence that When™ can fit seamlessly into their existing benefits environment."

Workday Wellness is available to U.S. customers now. Employers interested in connecting When™ can contact sales@forwhen.com.

About When

When™ is the enterprise platform for guided health insurance decisions at every qualifying life event. From early retirements and career pivots to involuntary exits and Medicare eligibility, When reduces costs and provides critical decision support for both employers and their employees when it matters most. When Insurance Agency, Inc. is a licensed health insurance agency operating in all 50 states, and its agents are licensed and non-commissioned. Backed by 7wire Ventures and ManchesterStory, When closed its Series A in 2026 and serves thousands of employers nationwide. For more information, visit forwhen.com.

Media Contact

Colin Koerin, colin.koerin@forwhen.com