Layoffs are never fun. They're one of the hardest calls a leadership team faces. Everyone in the room knows the decision affects real people's lives, and the company's reputation along with it. No one wants to be planning for one, but alas, it is the new norm.
So much so that for most companies, this isn't a question of if. It's a question of when. Workforce reductions have shifted from rare, last-resort moves to a regular feature of running a business. U.S. employers announced more than 1.2 million job cuts in 2025, up 58% from the year before and the highest annual total since 2020, according to Challenger, Gray & Christmas. For a variety of reasons, almost every enterprise will manage a major workforce transition sooner or later.
And yet, for all the energy we put into making someone's first day great, almost no one has built a real solution for their last one. Departing employees, the people who helped build the place, are left to navigate one of the most stressful stretches of their working life on their own. This costs the company, too, in the form of COBRA premiums, if subsidized, and claims rendering COBRA employees 300% more expensive than an active employee. The fix isn't complicated, but timing is critical. The best time to set up a better off-boarding experience is before a transition is announced, not after.
Workforce change isn't slowing down
We're in an unprecedented time. Macro events such as revenue declines, cybersecurity incidents, employees aging into Medicare, and M&A dominate the news, and each one drives a workforce transition and a coverage dilemma for the people caught in it.
Even setting those events aside, ordinary workforce churn runs high. About 38% of people quit within their first year, and 40% of that group do so within the first 90 days. And by one estimate, roughly 40% of American workers have been laid off or terminated at least once in their career. The old adage holds: the only constant is change.
So, benefits and total rewards leaders, if you've already experienced some transition, you can count on more. If you haven't, you can count on it coming. Preparing costs little. It's negligible next to the cost of being caught unprepared. It's the same logic as any insurance policy: you don't buy one because you're hoping for a disaster. You buy it so you're covered if one comes.
What "too late" actually costs
When off-boarding is an afterthought, the bill comes due in two places:
Cost. COBRA enrollees stay on your plan and generate up to three times the claims of active employees, raising costs for everyone who remains, including your active workforce. Departing employees who move to alternative coverage can reduce COBRA costs by up to 80%; they just need some guidance to weigh their options.
People and brand. How you handle someone's last day is part of your brand, not separate from it. A person left to sort out their own coverage during one of the most turbulent moments of their working life remembers exactly how they were treated — and so does everyone still on the team. The people who leave become your alumni: your future customers, your referral sources, the reviews a candidate reads before accepting an offer, and the boomerang hires you'd want back. Handle the exit with the same care as the first day, and that goodwill compounds. Fumble it, and that follows you too.
Why proactive beats reactive (and why it's lighter than you'd think)
Most companies don't implement a solution to address this for two reasons: they don't know one exists, and they can't see what it's costing them. Your true COBRA expense doesn't surface in the standard health-plan spend reports leaders prioritize from. It hides inside the data, so nothing flags it as a problem worth solving.
The good news: once it's on your radar, it's remarkably easy to solve for with When. We simply need two things you already have, your SBCs and your premium rates, and our implementation takes weeks, not months.
Once When is in place, you're covered. Like any good policy, it sits quietly in the background until the day you actually need it — and on that day, departing employees get a guided, personalized path to affordable coverage instead of a form letter, while your HR team gets a clean hand-off instead of a fire drill.
Because When's agents don't work on commission, the guidance is built around what's actually best for each person: an ACA plan with potential subsidies, a spouse's plan, or, for those who qualify, Medicare.
The win is mutual. Employers lower cost and risk. Employees get a better experience at the exact moment they need one. That's the beauty of preparing early instead of in a panic.
Set it up before you need it
You don't go shopping for the fire extinguisher during the fire. The companies that handle transitions well are the ones that decided how they'd handle them before the decision was ever on the table.
If you're a benefits leader watching the early signals — or a benefits consultant whose client is — the move is to put the safety net in place now, while it's a calm two-week project instead of a crisis. The question was never if your organization will face a transition. It's when. Let's make sure that when it comes, you're prepared.
See how When handles a transition the right way, schedule a demo. Or run the numbers yourself with the COBRA Savings Calculator.
