Amid an Aging Workforce and Rising Healthcare Costs, When Launches Medicare Cost-Savings Solution

The dual pressures of an aging workforce and rising premiums

CHICAGO — Employee healthcare benefits transition platform When announced the launch of Medicare support services on February 26, 2026, aimed at reducing healthcare costs for employers and their employees.

Currently, Medicare-eligible workers have become one of the fastest-growing segments of the labor force. According to Pew Research Center data, this group has grown by 33% over the past decade and now accounts for 7% of the total workforce. Meanwhile, employer-sponsored health insurance premiums in 2025rose 5% for individual plans and 6% for family plans, representing a cumulative increase of more than 25% since 2020. Employees aged 50 and older are often among the largest claim groups for employers. As some employees may choose to delay retirement or may not realize they are already eligible for Medicare, this could place further pressure on employers' already rising healthcare costs.

When's Medicare support services

"As the workforce ages, employers need to take steps to ensure they effectively support their employees and families while avoiding unnecessary financial risk to their business," said Andy Hamilton, CEO of When. "That's why we launched Medicare support services to help businesses and employees clearly understand their options, find the most cost-effective solutions, stay on top of deadlines, and simplify the process."

When's Medicare support services help active and departing employees evaluate and complete their transition to Medicare, while also providing education to employees who are not yet eligible so they can plan ahead. The Medicare offering has been piloted by existing customers, including a large Fortune 500 cloud computing company that is using the platform to support employees navigating health insurance changes.

With When's Medicare support services, customers can now include Medicare as a supported insurance plan type within their healthcare marketplace. Customers also gain access to a team of licensed Medicare specialists who can provide real-time, personalized employee consultations to help compare plans and costs. Additionally, When provides internal tools for HR teams.

Proactive education and early planning

When customers can also opt into proactive Medicare outreach and education content to help soon-to-be-eligible employees understand their options through on-demand webinars and one-on-one guidance. These services cover employees themselves as well as their dependents and household members, including those who are not eligible, aging parents, and spouses.

One employee in the pilot used When to plan for Medicare enrollment after their existing insurance premiums were set to increase by 100%. "When was incredibly useful and did all the heavy lifting for me," the employee said. "They made sure my key medications were covered and provided me with four plan options. All of this was done in a very short time, and they also handled all the deadlines. I couldn't have done it without When's help."

About When

Founded by two neighbors who experienced layoffs, When is the first workforce transition platform that helps organizations and employees navigate healthcare and benefits changes. Whether it's early retirement, career transitions, or involuntary separation, When reduces costs and provides critical support to employers and employees at pivotal moments. Since its launch in 2024, more than 6,000 companies have used the platform, and over 1 million employees have access to manage their benefits during career transitions through the platform. For more information, visit forwhen.com。