How SaaS Founders Are Rethinking Their Businesses With AI

by | Aug 28, 2026

This week, I hosted 43 SaaS CEOs at our 3rd annual Practical Founders Summit, held over two days in Phoenix.

It was awesome to meet in person with Practical Founders CEO Peer Groups members after meeting monthly on Zoom (in 5 groups) for another year to work on their businesses.

Most of these founders know each other very well from our monthly meetings and previous events in the last four years. These relationships compound.

We also have new Practical Founders members attending who fit right in.

These CEO peer groups are not for all SaaS/AI founders. They are just for Practical Founders building valuable B2B software companies without big outside VC funding.

There were no conversations about raising money — or selling their companies any time soon. Why sell when your company is growing and getting better every year?

This year’s conversation was about finding leverage with AI across your business to build a much better business next year.

Software coding is speeding up, and AI agents are doing more work across our businesses. Your competitors are doing that too.

So what?

We focused on how each of these founders is rethinking their businesses amid this crazy platform shift right now.

– Should we build more products for our sticky customers? Be more all-in-one?
– Go upmarket and finally compete with bigger competitors?
– Build agentic “system of action” capabilities on your system of record?
– Grow faster and sell our company sooner? Or get more profitable and resilient for the long term?
– Add services or hardware to solve the whole customer problem?
– Open up our platform with MCPs and APIs? Or protect our unique data?

Founders shared examples of all of these in every discussion. What are you doing? How’s that working? What does that change about your business?

No standard playbook works for every practical founder. We do it our own ways.

These are powerful possibilities to consider, test, and see if bolder bets make sense for them.

It’s a great time to be a practical SaaS founder. No SaaSpocalypse here.

I’m honored to work with these founders in our monthly peer group meetings, 1-1 as an advisor, and as host of our annual event.

Thanks to our expert speaker, Vincent Serpico, who shared his deep AI knowledge and talked about practical implementation and execution at scale with AI. This is real right now.

Thanks to our Practical Founders speakers, Shalin Jain, Andrew Wallace, and Jordon Comstock, who shared how they are finding leverage to grow better with AI, and what that made them rethink in their businesses.

Thanks to Practical Founders expert sponsors Mike Lyon at Vista Point Advisors, Matt Watson of Full Scale, Praveen Ghanta of DevHawk, Perry Rosenbloom of LaunchBay, and Austin Patterson, CFA of The One North Group. They came to help and share their knowledge.

Thanks to Donna Hacker on my team for helping to create a five-star event for these special people this year.

See you next year!

Greg Head posted this on LinkedIn on August 28, 2026.

Check out the comments and join the discussion on LinkedIn.

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