SaaS Had a Good Run. AI Is About to Rewrite the Playbook.

#saas #ai #technews #startup

For the past 20+ years, SaaS has been the dominant model for building and selling software.

We all know the story: licenses and maintenance faded away, subscriptions took over, and those who didn’t adapt went the way of Novell and DEC (old PC manufacturers for those too young to recognize the brands).

For a long time, the rules of SaaS felt stable. Build a solid product, grow steadily, raise capital, repeat. Incremental improvements were enough to keep you in the game.

But after reading Ivan Nikkhoo’s piece on the future of SaaS (worth your time), one thing is clear: that era is over.

AI is shaking up everything we thought we knew about SaaS.

Incumbents vs. Challengers

The giants (Microsoft, Salesforce, Oracle) have an unfair advantage: they’re the system of record. They hold the data. That means they’re hard to unseat, even if your product is technically better.

Startups and challengers can move faster and build smarter products. But here’s the harsh reality: better doesn’t always win.

Enterprise deals take years to close. Investors want to see traction long before those deals land. And buyers don’t like risk. They’ll choose “safe” over “better” unless you give them a reason not to.

The Startup Trap

This creates a brutal catch-22 for founders:

You need credibility to win enterprise deals.
But you need enterprise deals to build credibility.

Without a way to break that cycle, a lot of startups either burn out or get acquired early.

And as AI ramps up, the cycle gets faster and more unforgiving.

Why Founders Must Go on the Offensive

The old SaaS growth playbook — slow, steady, incremental — won’t cut it anymore.

AI is creating an entirely new wave of SaaS: vertical, AI-first solutions that rethink workflows in healthcare, finance, supply chain, legal, and beyond. These markets are massive, messy, and sitting on mountains of underutilized data.

That’s the opportunity. But it’s also the risk.

If you’re building in SaaS today, you need to ask yourself:

How do I differentiate against incumbents who already own the data?
How do I sell credibility before I’ve closed the big logos?
Am I building a product that’s truly AI-first — or just “AI-enhanced” in a market where others are rethinking the problem from the ground up?

The Next Wave

Here’s my takeaway after digging into Nikkhoo’s article:

The SaaS companies that win this transition won’t just be the ones that ship better products. They’ll be the ones that can sell better too.

Because when buyers default to “safe,” you need more than features to shift the conversation. You need to change how they see risk, urgency, and value.

That’s exactly why we built Playwise HQ — to give sales teams the competitive intelligence they need to win those high-stakes conversations against incumbents. Real-time battlecards, sharper positioning, and intel that doesn’t collect dust.

👉 If you’re building in SaaS or AI and want your reps to land deals against the giants, check out Playwise HQ.