Practical Founders Peer Groups

It’s hard to create a valuable software company without big funding.
And it’s lonely to be a software startup founder.

Get the right support to build a valuable SaaS company faster.

Apply Now

Now you can work on your business with a trusted group of practical SaaS founder peers who are going through the same crazy hard stuff and who can support you every month.

A Practical Founders Peer Group is a committed and confidential group of eight founders/CEOs who are creating valuable B2B SaaS companies without big funding.

Each Practical Founders Peer Group is personally curated and moderated by Greg Head. We meet every month on Zoom for three hours at a scheduled time.

The monthly peer group meeting is a fast-paced and structured meeting to help serious founders get savvy perspectives and honest feedback on their biggest challenges. 

You also get access to 1-1 advisory support working with me, Greg Head. I’m an experienced SaaS entrepreneur and operator who has grown two software companies from startup to $100 million in revenues, including one IPO. 

Now I help serious practical SaaS founders all over the world create valuable software companies without big outside funding.


create a valuable software company faster

Practical Founders Peer Groups

Be part of a committed and confidential group of practical founders who are creating valuable software companies without big funding—just like you. I am confident that every member will experience million dollar+ impact in their business every year.

Greg Head

Current Practical Founders Peer Group Members in 5 Different Groups

Every month we will help you make progress in these three areas:

  1. Drastically improve decision-making in the crucial areas where you are struggling.
  2. Learn deep insights on what’s working to grow your B2B SaaS company most effectively.
  3. Get the emotional support you need to stay sane on your crazy startup journey.

Practical Founders Peer Group membership is $5,000 a year. Apply now to have a brief conversation with Greg Head to see if it’s a good fit right now.

Practical Founders Peer Groups based on your growth stage:

Scale Groups – Growing from $1 million to $10 million ARR

  • You have a clear customer focus and your core product is expanding steadily
  • Your company has over $1M in annual recurring software product revenue 
  • You just need more revenue to fund your investments and hires. You are not trying to raise VC funding.
  • You may sell the company at some point when it is much bigger or you can run it as a happy, profitable business

Growth Groups – Getting to $1 million ARR

  • You have a working product and paying customers
  • Your software business has between $50,000 and $1 million ARR (annual recurring product revenue)
  • You and your small team are getting a lot done 
  • You are experimenting with customers, messages, pricing, features, and channels to grow

Included with your annual commitment:

  • Monthly peer group meeting, moderated by Greg Head, to work on your business with serious B2B SaaS founders just like you
  • Expert Zoom interviews to ask an experienced practical founder any questions in a private members-only session
  • One-on-one advisory support with Greg Head each quarter on any topic
  • Access to peer CEOs and expert mentors who have the specific experience you need
  • Private Slack group to ask questions and share resources with your peers

2024 Enrollment is Open

Become a Practical Founder Peer Group members this year. Let’s have a conversation to see if it’s a mutual fit for us to make this commitment together.

About Greg Head

As you may know, I have had a successful 30-year career starting, growing, and scaling software companies. I worked crazy hard with amazing people. I had some big successes and countless opportunities to learn along the way.

Now I help serious software company founders all over the world almost every day via Zoom, phone, and my popular LinkedIn discussions. I am an active mentor, paid advisor, and tech community instigator.

Peer Groups FAQs

Just fill in the simple application form 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 and at least 75% attendance in our monthly 3-hour peer group meetings. 

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

Several peer groups I have previously led kept going every month for over 5 years.

Practical Founders Peer Group membership is $5,000 a year—or $1,500 per quarter 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. It gets better and more valuable each month.

Yes, Some minimal revenue from real paying customers is a requirement to participate in a Practical Founders Peer Group. This can be a few customers and $20K-$50K recurring product revenue to start, but some revenue and customer traction is required. 

Here’s why:

  • When you are building your product and trying to find your first paying customers, our groups can’t offer much value to you yet in how you build your particular product for your particular customer. 
  • When you are pre-revenue, I recommend you spend all your money investing in building a valuable product for the right first customer that they will pay for. You should use free online and available mentor resources to help you at this stage. 

We can still have a conversation about the eventual value to you of a Practical Founder Peer Group when you get your first customers. Feel free to sign up to have a conversation with Greg and possibly participate in a peer group as you grow. 

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. There are CEO peer groups in every major city which include CEOs and owners of companies of similar sizes across industries, typically between $5-$50 million in revenues. 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 who are 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 may have an onsite in-person meeting for each of the peer groups at some point each year after we get started. 

Greg Head currently runs five Practical Founders Peer Groups with 40 active CEO members. There are available 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 urgent challenges, I also work with a few founders every quarter 1-on-1 as a paid strategic advisor. 

If you want to work with me as an advisor, fill out the Peer Group form here and let me know if you’re interested in a 1-1 advisory in the notes. 

I’ll follow up to discuss what you really need and how my practical advisory program might be a good fit.