This is why you hate insurance
- Claire Baker
- 2 days ago
- 1 min read
Your broker doesn’t set up payroll. Your payroll admin doesn’t grok benefits. And when the software doesn’t talk to each other, things break.

I worked with a small group where the new plan started... but payroll never heard anything about it.
The benefits system didn’t push the new elections to the payroll software. With no data about the new plans, payroll didn’t know what to deduct. So it didn’t deduct anything.
🧧 Ka-ching! Paychecks went up by about $100 per person. Score!
...Except they still owed that money.
When we caught it a few pay periods later, we had to explain to everyone that they’d need to pay it back. It wasn’t just messy. It was awkward. People were confused and angry.
This is what happens when no one owns the full process.
The broker sells the plan but doesn’t touch payroll. The payroll admin follows what the system shows. The tools don’t connect. No one’s tracking the handoffs. No one even knows what happens in other steps of the process.
These problems don’t show up right away. They lie in wait until someone balances the books and notices thousands of dollars missing.
No wonder people hate insurance.
Fixing benefits administration isn’t about a single glitch. It’s about understanding the full stack, from tax codes to tooling, carrier incentives to employee comms. Especially the things PEOs don't cover.
If only that skillset existed in one person...
👋 Hi. I'm Claire.
If your benefits are a mess and you're tired of fixing the same mistakes, let's talk. Because fixing a deduction is easy. Rebuilding trust? Not so much.
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