For Bootstrapped B2B SaaS Founders with $1M–$20M ARR

Practical Founders CEO Peer Groups

At your stage, one wrong decision costs you 12–24 months and millions in company value. Stop making those decisions alone.

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Active Peer Groups

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SaaS CEOs in All 5 Groups

0yrs

Average Member Tenure

11%

In-person Summit Attendance

This Is Not a Course, Community, or Mastermind

Each Practical Founders CEO Peer Group brings together 8–10 bootstrapped SaaS CEOs at similar stages — meeting monthly, working through real strategic challenges, moderated by Greg Head.

There are no templates. No universal tactics. No rotating group of people.

This is a consistent group of SaaS founders at similar stages of growth, facing big decisions every month, meeting monthly confidentially, and working through real situations in detail.

This is where you bring your hardest decisions.

This works because the same founders show up every month for years. They know your business, your team, your numbers, and your blind spots. Trust compounds.

Unlike cross-industry CEO groups, every founder here sells B2B software. Unlike other SaaS communities, the same members show up every month — for years.

Apply for a CEO Peer Group

Here are some examples of the kinds of topics and questions we work on each month:

Growth & Strategy – Should we invest more to grow faster or focus on profitability this year?
Leadership & Team – My lead dev won’t step up as CTO. Do I coach them or hire above them?
Pricing & Revenue – We haven’t raised prices in 3 years. How do we launch increases without losing customers?
M&A & Exit Planning – I’m getting weekly buyer inquiries. What should I actually do with these?
AI & Technology – How do I get my dev team create business impact faster with agentic coding?
Personal Challenges – A serious personal issue is affecting my ability to lead. How do I manage both?
Funding & Ownership – Should I take on a little practical debt funding to accelerate this year?

What a Practical Founders Peer Group Includes

Monthly sessions: Scheduled 3-hour structured and confidential Zoom meetings with 8-10 peer SaaS CEOs, personally moderated by Greg Head.
Curated group: All members are B2B SaaS founders with similar revenue range. All bootstrapped or lightly funded.
Annual Summit: In-person private conference in Phoenix each August. 90% of members attend.
1-on-1 advisory: Direct access to Greg between sessions for your most pressing challenges.
Expert network: Referred specialists in legal, M&A, growth equity, dev, etc. who join monthly calls and our Summit.
Long-term commitment: Members stay for years. Your group becomes a trusted advisory board and friend group.

Investment

$6,000–$10,000 per year based on company stage. Annual commitment. No initiation fee. Annual Summit conference is $1,500 additional.

This Requires Commitment

Monthly time investment (3 hours)
Consistent participation (75%+ attendance expected)
Willingness to share real challenges—and help others with theirs
Annual 2-day Summit in-person event

This only works if you take it seriously. Your peers will.

What Current CEO Members are Saying

The Annual Practical Founders Summit

Our amazing annual in-person session.

Once a year, all Practical Founders peer group members meet in person for a private, 2-day summit. This isn’t an open conference. It’s just Practical Founders who already know each other.

2-day private event (Phoenix, late August)
90%+ member attendance
Expert guests and founder-led deep dives. No fluff content.
Small group discussions, shared meals, real conversations

Is This Right for You?

This is built for you if:

Founder-CEO of a B2B SaaS with $1M+ ARR
Bootstrapped or lightly funded
Growing and want to grow smarter
Willing to share openly and help others
Playing with practical AI to gain leverage
Can commit to monthly sessions and annual Summit

Not for:

Pre-revenue or still finding product-market fit
Raised or planning to raise institutional VC
Looking for templates, playbooks, or a course
Schedule won’t allow consistent attendance
Prefer answers alone over working through problems with peers

What Founders Say After Joining

Led by Greg Head — SaaS Operator, Not Just a Facilitator

Greg has been building and scaling software companies for 30 years, including leadership roles in multiple startup-to-scale journeys.

Today, he works directly with 45 SaaS CEOs every month and moderates multiple peer groups.

He also interviews successful founders on the Practical Founders Podcast, with over $11B in founder equity created by guests.

If You’re Facing Bigger Decisions, This Is the Right Time

Most founders at this stage are making these decisions alone. You don’t have to.

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Frequently Asked Questions

How does the application and acceptance process work?

You apply with a few details about your company and current situation. If it looks like a potential fit, Greg will schedule a short call to understand your business, current challenges, and which group would be right for you. Groups are carefully curated by stage, situation, and founder mindset. Not everyone is accepted—we’re focused on building the right groups, not filling seats.

What's the time commitment?

One 3-hour group session per month at your regularly scheduled time. That’s the core commitment. Most members treat this as one of the highest-leverage blocks of time in their month. There’s occasional communication between sessions — with Greg for 1-1 deep dives, expert guest Q&A, and some Slack with your group.

What is the financial commitment?

$6,000–$10,000 per year based on company stage. Annual commitment with no initiation fee. Includes all monthly sessions and 1-on-1 advisory with Greg. Annual Summit conference is $1,500 additional.

Are these peer groups for founders who are just starting out or pre-revenue?

No. This is for founders with real traction—typically above $1M ARR—who are making meaningful business decisions and not scrambling every day with no space to think strategically.

What actually happens in a typical session?

Each monthly group session on Zoom is structured, focused and fast-paced, with Greg planning and moderating every meeting. Typically, 2–3 founders bring a real decision or challenge they’re working through. The group goes deep into those situations.

How are the peer groups formed?

Each group is carefully curated by Greg Head. We match founders based on revenue stage (roughly $1M-$5M, $5M-12M and $10M+ ARR) and type of challenges at each stage. Companies are non-competitive.

Is everything confidential?

Yes. What’s shared in the group stays in the group. Founders openly discuss real numbers, challenges, team issues, and strategic decisions. That only works because confidentiality is expected and respected by everyone.

How is this different from EO, Vistage, or other peer groups?

Most CEO peer groups are broad by design. Practical Founders is different: 100% B2B SaaS founders, bootstrapped or lightly-funded, similar revenue stage, focused on real decisions—not general discussion.

What if I miss a session?

We expect consistent participation—typically at least 75% attendance. The value comes from continuity, trust, and shared context over time.

How do I know if this is worth it?

Most members will tell you that they made many better decisions each year—or avoided mistakes—which more than paid for the investment. In a strong peer group, you get context from founders in similar situations, pattern recognition from real experience, and faster, more confident decisions.