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Kevin Andrews

PEO Software Never Tried to Be the Star. That's Why It Won With SMBs

Every few years, some HR Tech company swears it's finally here for small business. Two funding rounds later it's chasing enterprise logos, and the customers who got it off the ground are stuck on hold.

PEOs (Professional Employer Organizations) have been taking those calls the whole time.

A professional employer organization handles HR, payroll, benefits, and compliance for small companies that can't staff those functions themselves. Kevin Andrews has watched the market circle small business for three decades. He's Board Advisor and Chief AI and Transformation Officer at PrismHR and Vensure Employer Solutions, which build the software PEOs run on. Before that, he co-founded SmartBen and later ran technology at a public company serving 30 million people.

He arrived on the PEO side right as AI made it cheap for anyone to build tools around HR systems, including PEOs' own customers. That shift raises the stakes on the parts of PEO software that can't afford a bad day. It also settles an old argument about whether PEOs were ever really tech companies.

Why PEO Software Wins the SMB Market Others Abandon
  33 min
Why PEO Software Wins the SMB Market Others Abandon
Work Tech Weekly
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HR Tech Has Been Running the Same Play for 30 Years

Small vendors want to move upmarket. Big vendors want to grow TAM by moving down. Kevin says it's "been that same strategy for 30 years," and it rarely works in either direction.

Call it HR tech's Groundhog Day, except Bill Murray eventually learned something. Enterprise complexity crushes products built for small companies, and the margins don't survive the trip.
For years, pure SaaS players had a tidy explanation for why PEOs didn't count as tech: they were service businesses with software attached.

That take was always shortsighted.

Kevin's view is that the service was the whole reason small businesses signed up. "Where PEO wins is on service plus expertise. So it's not just software." A small business owner doesn't have an HR team to absorb a compliance issue or a payroll problem that eats two days, so the PEO absorbs it for them.

The software plays a supporting role, and Kevin says so plainly: "Our role is just to power that differentiation with better tech." That humility helps explain why PEO software has outlasted plenty of platforms that were supposed to replace it.

Anyone Can Build Around Payroll Now, Which Makes the Core Worth More

During a six-hour business review with a large customer, Kevin kept hearing the same request. Show us your roadmap so we don't build the same thing.

That customer can now spin up its own tools with AI, and it wants to point that effort somewhere useful. "We wanna stay away from the core."

Kevin is all for building at the edges. His worry starts when something vibe-coded gets bolted onto payroll or benefits and has to survive real use.

The demo always looks great.

"You get 10 people on it and all of a sudden they have a problem."
AI is making his own teams ship and test faster. The core still has to be right every single time, because that's where customers decide whether to trust you. "The plumbing is mission critical, though," Kevin says. "It's where the trust is built or really lost."

When every customer can build its own widgets, the vendor's job gets narrower. It also gets a lot harder to fake.

Small Businesses Don't Want More Features. They Want Fewer Headaches.

Asked where small businesses are still underserved, Kevin doesn't hesitate: "enterprise-grade insights without enterprise-grade complexity or pricing."

His fix is conversational. An owner gets flagged that an employee's hours are missing before payroll runs, then handles it in a message. The ask can be as simple as "hey, I want to approve payroll from my phone."

He expects benefits to follow by 2030, trading "this 30-minute kind of panic every November" for year-round guidance that tracks a new baby or a raise as it happens.

For a guy whose first company existed to kill the paper enrollment form, it's a pretty fitting sequel.

Kevin's advice to his younger self explains the whole 30-year loop. Choose customers carefully and "go serve 80% of the market." Customize for the demanding 20%, and your technology gets locked into a shape nobody else can use.

That's how most HR tech vendors drifted away from small business. One custom deal at a time. PEOs built their whole model around SMBs. The SaaS crowd called that a service business and moved on. Now that anyone can vibe code the widgets, staying looks a lot like the product.

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