SaaS Before it was Cool (or Accurate)

Before I worked in SaaS, I worked in corrections.

Which means technically, I also worked in SaaS.

Just not the version everyone on LinkedIn won’t shut up about.

At the jail, we had a system. Inmate tracking. Incident logs. Movement. Medical. Everything.

It was called SaaS.

Except… it wasn’t.

It was on-prem. Hosted locally. Maintained manually. Upgraded when someone remembered or something broke.

No subscriptions. No “per seat” pricing. No customer success team asking about adoption.

Just a system that existed. And if it went down, things got very real, very fast.

Then I moved into “modern SaaS.”

Cloud-based. Subscription-driven. User-tiered pricing. Quarterly business reviews. “Time to value.”

And I remember thinking…

We are not talking about the same thing.

Somewhere along the way, SaaS stopped being about how software is delivered …and started being about how software is monetized and scaled.

That shift matters more than people think.

Because it changes how we build. How we sell. How we support. And most importantly…

How we define success.

In corrections, success was simple:

Does the system work? Is it reliable? Does it hold up when everything else doesn’t?

No one cared about feature releases.

They cared about function under pressure.

In SaaS today, success sounds like:

Adoption Engagement Expansion Retention

All valid. All necessary.

But sometimes I think we’ve drifted a little too far from the original question:

Does this actually work when it matters?

Here’s the part no one really talks about:

A lot of “SaaS” in regulated or legacy industries still looks a lot like what I used in corrections.

Hybrid deployments. Heavy dependencies. Manual processes hiding behind “automation.” “Cloud” that still requires three vendors and a prayer to function.

But we sell it like it’s plug-and-play.

We sell it like it’s instant.

We sell it like it’s easy.

And then Professional Services gets the call.

That’s why I don’t get caught up in the SaaS label anymore.

Because whether it’s:

Corrections systems Mortgage CRMs Retail platforms Or anything in between…

The real work is always the same:

Make the system usable. Make it reliable. Make it deliver value in the real world, not just the demo.

The industry changed the packaging.

The mission didn’t.

Final thought

SaaS isn’t defined by the cloud.

It’s defined by whether the software actually shows up when the operator needs it most.

Everything else is just pricing strategy.

#SaaS #ProfessionalServices #CustomerSuccess #Fintech #Leadership #Operations #BuildInPublic