In HR Tech Cube: The Medicare Transition Employers Can’t Ignore

Co-Founder Dan Wertheimer wrote for HR Tech Cube about a shift many benefits teams haven’t fully connected to their strategy: a rapidly aging, working-past-65 population, and the compliance rules that leave employers unable to actively guide these employees toward Medicare, even when it’s the better fit for everyone involved.

Dan walks through why Medicare Secondary Payer rules keep employers’ hands tied, why Medicare’s enrollment windows are easy to miss and expensive to get wrong, and why the fix isn’t a policy change or a memo. It’s building real transition support into the benefits strategy itself: reaching employees before they turn 65 and connecting them with licensed guidance they can actually use.

His larger point is philosophical as much as tactical: employers have long treated the Medicare transition as someone else’s problem, something that happens quietly after employment ends. But with more people working well past 65, employees are still looking to their employer as the anchor of their healthcare experience.

Highlights from the article

• Over 11 million Americans age 65 or older are still in the workforce.

• Medicare Secondary Payer rules keep employers from steering active employees over 65 toward Medicare, with real compliance risk attached to getting it wrong.

• Under ACA age-rating rules, carriers can charge older employees several times what they’d charge a 21-year-old for the same plan.

• Medicare’s enrollment windows are easy to miss and unforgiving: missing one means a permanent premium penalty.

• Dan’s proposed fix is building proactive, licensed transition support into the benefits strategy itself, before employees turn 65.

Are you ready for When?

Curious what proactive Medicare guidance looks like in practice for your workforce? Learn more about our Medicare support, or schedule a demo to see the platform in action.