When, an employee healthcare transitions platform, today announced the launch of Medicare support services to reduce healthcare costs for both employers and their employees. 

Medicare-eligible workers are the fastest-growing segment of the labor force, growing 33% over the last decade to comprise 7% of the workforce today. At the same time, employer-based healthcare premiums in 2025 rose 5% for individuals and 6% for families - up more than 25% since 2020. Workers aged 50+ typically represent one of the largest claimant groups for employers, and as workers may choose to delay their retirement or may not realize they’re eligible for Medicare, this potentially puts further strain on employers’ already-rising healthcare costs. 

“As our workforce gets older, employers need to take steps to ensure they’re effectively supporting their employees and their families, without introducing unnecessary financial risks to the business,” said Andy Hamilton, CEO of When. “That’s why we’ve rolled out our Medicare support offerings to help companies and their employees get a clear picture of their options, find the most cost-effective solutions, stay on top of deadlines, and make it easy to take action.” 

When’s Medicare support services helps both active and departing employees assess and navigate switching to Medicare, as well as educating not-yet-eligible employees so they can plan for the future. When’s Medicare offering has been piloted by existing customers, including a major Fortune 500 cloud computing company that is using the platform to support employees navigating changes to their health coverage. 

Through When’s Medicare support services, customers can now access Medicare among the types of supported insurance plans in its healthcare marketplace. Customers also have access to a dedicated team of licensed Medicare agents on hand to provide real-time, individualized employee support to compare plans and costs, as well as an internal tool to support HR teams.  

In addition, When customers can enroll for proactive Medicare outreach and educational content to help employees approaching eligibility learn about their options through both on-demand webinars as well as one-on-one guidance. These offerings include guidance for employees and their dependents and household members, including non-eligible participants, aging parents, and spouses.  

One employee piloting the new tool used When to navigate their Medicare enrollment after their existing insurance premiums were set to increase 100%. “When was so helpful and did all the footwork,” they said. “They made sure my critical medications were covered, and came up with four plans for me to choose from. All of this was taken care of in an incredibly short amount of time, and they helped me manage all the deadlines. I could not have done this without the help of When.”