Practical Founders Peer Groups

Just fill in the simple application form on this page with basic information about your company and your situation.

Greg Head will follow up with you directly to answer any questions you have and make sure it’s a perfect fit for you right now.

Membership in a Practical Founders Peer Group requires an annual commitment of at least 75% attendance in our monthly 3-hour peer group meetings.

These groups will continue for many years. As they grow, some members will move to a different group level, new members will be added, and some founders will sell their companies and “graduate.”

Practical Founders Peer Group membership is $6,000 a year with an annual commitment.

Peer groups require equally high commitment from all members. These powerful relationships don’t just develop in one or two meetings; they get better and more valuable each month.

We believe that when serious founders support each other, sustainable growth follows. That’s why we’re dedicated to creating peer relationships that build lasting value – turning every challenge into an opportunity for growth, every meeting into a catalyst for clarity.

My Practical Founders Peer Groups are best for serious B2B SaaS founders with software product revenues between $1M and $10M ARR, with some exceptions. 

When you are starting out, finding product market fit, and learning to sell, there isn’t as much value that a group (or me) can add that can help you get to the next level. I have tried it, and it’s really tricky to help consistently and usefully every month. It’s mostly up to you.

The work we do together is challenging to directly apply to your first customers, products, and revenues. It’s hard to make it valuable enough for founders until revenue grows and your problems look more “typical,” which usually happens around $1M ARR or at least 50 customers.

A CEO peer group is an organized group of CEOs who meet monthly in a confidential setting to work through their business challenges and share insights. In a trusted and confidential environment, it becomes a powerful forum to discuss your most difficult challenges and get alternative perspectives. These peer-CEO relationships usually become deep and lasting.

CEO peer groups are not new. They exist in every major city and include CEOs and owners of companies of similar sizes across industries, typically with revenues between $5-$50 million. Some groups are facilitated by a coach, and others are self-moderated.

There are popular peer group organizations for CEOs and business owners that have local chapters in most cities around the world, including the Entrepreneurs Organization (EO), Vistage, and Young Presidents Organization (YPO). Each requires significant financial and time investment with local, in-person, full-day meetings every month for their groups. Most members have businesses in other industries like manufacturing, healthcare, services, or distribution.

Unlike these groups, Practical Founders Peer Groups are just for founders of startup and early-stage B2B software companies. We focus exclusively on the serious issues facing practical founders growing valuable software and SaaS companies without big outside funding.

Each peer group meets monthly over Zoom for 3 hours at a scheduled time. Meetings with Greg are also by Zoom or phone.

We have an annual in-person Practical Founders Summit conference in August for Practical Founders Peer Group member CEOs.

Over 80% of peer group member CEOs attend in person. It’s a great event for connecting with peer CEOs, learning from experts, and sharing meals and events to trade tactics and strategies.

Greg Head currently runs four Practical Founders Peer Groups with 31 active CEO members. There are slots in one of the groups and a waitlist for our next groups.

If a Practical Founders Peer Group isn’t a good fit for you because of time zone conflicts or your urgent challenges, I also work with serious software founders one-on-one as a paid strategic advisor.

I’ll work with you on your biggest strategic challenges and share my 30+ years of experience building fast-growing software companies and what I learn from the 40 founders I work with every month.

If you want to discuss working with me as a strategic advisor, fill out the contact form, and we can chat. You can also send me a direct message on LinkedIn.

I’ll follow up to discuss your needs and see how my practical CEO advisory program could be a good fit for you.