Because some of a company's most sensitive and highly-regulated data flows through the HRIS, very few people get full insight into everything that’s happening in the platform. HR software is a pretty blind item. You don’t get to try before you buy. Even with the providers who give you a sandbox, it’s hard to get a true sense of performance until you have live data.

How does this even slip through? For THREE YEARS? Part of it had to do with a quirk of how taxes work in reciprocity states like Wisconsin. Part of it was because state agencies don’t talk to each other. And implementation teams aren’t tax experts. And some payroll providers don’t have enough error flags for situations like this. And humans are flawed. They make mistakes.

Have you ever wondered what it would be like if you threw five cats in a bag and asked them to run your payroll? Or have you already tried Paylocity?

To get this one solved, I had to engage Claire-en mode. I demanded to speak to a manager. When the first person wouldn’t call a manager, I hung up and called again.

You know why their checks are cut by ADP? Because most of them work at big, old companies and switching payroll providers is really, really hard at that size. And because people don’t know any better.

The PEO issues the paycheck, but you pay the wages, taxes, and employer portion of benefits. Since the PEO is the employer on paper, they handle registering for state agencies and tracking compliance laws. And because PEOs can pool all of their client-employees, you get access the more affordable and flexible large-group benefits.

I just really, really love Rippling. Because I’ve used it. And I’ve used its competitors. And, in my opinion, Rippling is better. At (just about) everything.

For my small business clients (who aren’t considering a PEO), the decision often comes down to Bamboo or Gusto. Both Bamboo and Gusto have clean, easy-to-understand user interfaces with cute graphics that really do make dry and stressful processes less intimidating and occasionally “delightful.”

Deel is like if a pickup artist did payroll. Deel is the stereotypical tech-bro, “move fast and break (your) things,” the-rules-are-for-thee-and-not-for-me, all-glitz-no-substance disappointment. It looks pretty in the demo, even if those fancy buttons and cool apps never work as expected.

But if you have a product or agency that was created to manage private and sensitive data, it is incumbent on YOU to create processes and tools to help users handle that information properly.

Before you start planning how you’ll spend that “free” paycheck before your finance department re-balances the budget for 2026 you need to know that your payroll provider is probably smart enough to anticipate this. There are two methods that payroll providers use to solve the 27-paycheck problem: Pro rata and pay as usual.

Here are five examples of mundane breakdowns that I’ve seen lead to payroll errors:

Most teams frame it like a software switch. In reality, you’re rebuilding your company’s approach to employee data, payroll, benefits, and compliance from scratch.