CEO Peer Groups for Serious Bootstrapped SaaS Founders
Practical Founders helps serious bootstrapped SaaS CEOs make better decisions, grow faster, and build real founder equity value.
You’ve built a real SaaS business. Now the decisions are harder. AI is accelerating everything—competition, expectations, and the cost of getting it wrong.
Saas CEOs in 5
Active Peer Groups
Active Members with
$10M+ ARR
Average Years
Member Tenure
Combined Member
Equity Value at 5X
Current Active Peer Group Members
You’re Building Something Valuable. But the Biggest Decisions Still Land on You Alone.
Your company isn’t a startup anymore. You have customers, revenue, and a team counting on you. Your decisions keep getting bigger.
Should you hire a VP of Sales or promote from within? Raise prices and risk churn? Take on some funding to accelerate, or stay lean? Acquire that competitor? Sell while you’re ahead?
You can’t pressure-test these with your employees. Your spouse listens but can’t weigh in on SaaS go-to-market tradeoffs. Even your exec team has blind spots — or an agenda.
Local CEO peer groups like EO and Vistage are full of small business owners of all types, but nobody’s talking about ARR growth, churn, or how to structure a founder-scale SaaS exit.
So you figure it out yourself again. It can work, until it doesn’t.
What’s missing isn’t more content or more advice. It’s a small group of founders who actually get the SaaS+AI game this year. People running $3M–$15M SaaS companies without big funding, facing the same kinds of decisions, willing to be honest about what’s hard.
Practical Founders CEO Peer Groups
Work on your biggest business challenges with a committed group of 8–10 SaaS CEOs at your stage. Every month for 3 hours, you’ll get honest feedback, outside perspective, and real decisions and tradeoffs from founders who understand you and your vision.
Personally curated and moderated by Greg Head. 75% attendance required. Members stay for years. This isn’t casual networking. It’s the most important meeting on your calendar.
- Sam founders, every month – for years
- Similar stage and challenges
- Moderated by an experienced Saas operator
For Bootstrapped SaaS Founders at $1M–$15M ARR
This is for founders who have real traction—and real decisions to make.
For:
- B2B SaaS and AI software with recurring revenue
- Bootstrapped or lightly-funded
- Founder-led
- Facing growth, hiring, or strategic challenges
Not for:
- Still figuring out product-market fit (under $1M ARR)
- Planning to raise significant VC funding
- Looking for tactics and playbooks
Better Decisions.
Less Risk.
Faster Progress.
The most costly mistakes at this stage are bigger decisions that are hard to undo—not execution mistakes.
In a Practical Founders Peer Group, you will:
- Pressure-test decisions before committing
- Learn from founders in similar situations
- Avoid expensive mistakes
- Learn lessons and see what works for other founders
- Work through your hardest decisions with founders at your stage
What Founders Say After Joining
"It's a monthly therapy session where we can all relate to each other's problems even though we're in different industries and countries."
"I can point to a couple of really key decisions I made as a result of the feedback from the group. I wouldn't have made those hard decisions without the push."
"The quality of this peer group is completely night and day better compared to other CEO peer groups I have tried."
Led by Greg Head — 30-Year Practical Software Operator
I’ve been in the software and SaaS trenches for 30 years. I was a leader in the startup-to-scale journeys of three CRM companies, including one that went public, which I co-founded. Now I work directly with 45+ SaaS CEOs every month and moderate five Practical Founders peer groups.
I’ve interviewed 160 founders on the Practical Founders Podcast who have created over $11 billion in founder equity — without VC funding. I see what’s happening this month across 45 founders. I’m here to help you build your valuable software company your way.
Practical Founders Podcast
Real stories from founders who built valuable companies without big funding
Every week, Greg interviews a successful software founder who started, grew, and often sold a valuable software company without big VC funding. Over $11 billion in founder equity value has been created by 150+ founder guests — an average of $70 million per company.