Opinions expressed by Entrepreneur contributors are their own.
Key Takeaways A founder’s perspective on navigating rising health insurance renewals while balancing business realities and employee expectations.
Practical reflections on how growing companies approach benefits decisions, communication and renewal planning amid escalating healthcare costs.
If you run a business, there’s a familiar email you probably opened this fall: the one from your benefits broker with your 2026 health insurance renewal.
You scroll. You see a double-digit increase, and your stomach drops. You want to do right by your team. You also have a P&L to protect. And the three standard options you’re handed — pay the increase, raise deductibles or push more cost onto employees — all feel bad in different ways.
Over the last five years of building and scaling my company, I’ve lived that renewal meeting many times. Our headcount grew from a few dozen people to more than a hundred. At times, our brokers brought us quotes that were shockingly high. We pushed back, redesigned plans and tried to balance three realities:
Costs are going through the roof.
We want our people to feel genuinely supported.
We cannot absorb every increase without consequences elsewhere in the business.
This is not legal or actuarial advice. I’m not a benefits consultant. I’m a founder who has had to sign the renewal and then look my employees in the eyes. This is the playbook we’ve developed — one that any employer can adapt as you roll out your 2026 coverage and start preparing for 2027.
... continue reading