EO and VIstage CEO Peer Groups Don’t Get Deep SaaS

by | Aug 20, 2025

CEO peer groups like Vistage, YPO, and EO are great. But they don’t help bootstrapped SaaS founders answer their deep questions or understand the unique conditions of growing a valuable software company.

Working on your business (and yourself) every month with other CEOs, founders, and owners at the same stage is always powerful and helpful.

You get insights, knowledge, support, appreciation, perspective, and motivation–when you and your peers are committed to helping each other do the right hard things each month.

But what happens when almost all your important questions require industry knowledge AND the context of your particular slice of that industry?

I talk to founders every month who got a lot out of their CEO peer group and really enjoyed EO (Entrepreneurs Organization), YPO (Young Presidents Organization), and Vistage.

But they are stuck because nobody in their group is in the software business.

They realize that generic answers about hiring, growth, financials, funding, and exits become less helpful after a point.

They know that their leverage–to grow faster, be more efficient, use AI, improve pricing, hire better, and exit successfully–all require very deep knowledge of the B2B SaaS game, as it is played right now.

Not last year. Not generically. Not in the hype of Silicon Valley.

That’s why I created Practical Founders CEO Peer Groups.

There are currently 38 serious SaaS CEOs in one of my 4 Practical Founders peer groups, from all over the world.

We meet every month to go deep and work on the biggest and hardest challenges each founder is facing.

We meet in person once a year for our annual Practical Founders Summit. It’s happening next week in Phoenix.

Founders bring their challenges and their superpowers to move their businesses forward faster—every month.

I didn’t invent CEO peer groups. I didn’t invent bootstrapping or B2B SaaS.

It’s not for any B2B software CEO. It’s for practical founders.

Practical Founders build valuable software companies without big VC funding.

I interview a practical founder success story every week on my Practical Founders Podcast.

These founders create exits of $20M-$200M–for the founders. That’s not VC territory (or speed).

CEO peer groups aren’t a great fit for every founder or CEO.

And the Practical Founders CEO peer groups aren’t for most SaaS founders.

About a third of our active members were previous members of EO, YPO, or Vistage. A few still do both.

Learn more at practicalfounders.com/peer-groups.

Greg Head posted this on LinkedIn on August 20, 2025.

Check out the comments and join the discussion on LinkedIn.

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