Work Directly with Greg Head

Focused, 1-on-1 strategic advisory for SaaS founders working through important decisions

For founders who want to move quickly on their biggest challenges, I offer a small number of 1:1 advisory engagements each quarter.

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Two Ways to Work Together

CEO Peer Groups

Build a longer-term relationship
Work monthly with other founders like you
Benefit from multiple perspectives
$6,000/year

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1:1 Advisory

Work fast and deep with Greg 1-on-1
Biweekly 90-minute deep dives
Unlimited access between calls
$5,000–$7,500/quarter

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This Is for Founders Who Need to Move Fast

You’ve got a decision that can’t wait for next month’s peer group meeting. Or you want the depth of working with someone who can see your entire strategy system — product, GTM, team, pricing, positioning, exit — and connect the pieces.

This Is a Good Fit If

You have an urgent strategic decision — hiring a key leader, pricing restructure, acquisition opportunity, exit preparation
You want depth on your specific situation, not general advice
You prefer 1-on-1 intensity over group dynamics
Your schedule or time zone makes peer group timing impractical right now

What We Work On

Hiring or upgrading key leaders
Growth vs profitability decisions
Pricing and packaging changes
Exit timing or acquisition opportunities
AI strategy and execution
Organizational scaling challenges

Usually, it’s not one issue—it’s how everything connects.

What Greg Head Brings to the Table

He’s done it: Built and scaled two software companies to $100M+ in revenues, including one IPO.
He sees what’s happening now: Works with 45+ SaaS founder-CEOs every month. Advises from live pattern recognition across dozens of companies.
He thinks in systems: Strategy, go-to-market, pricing, team, operations, exit readiness — Greg sees how the pieces fit together.
He has the network: 175+ podcast interviews and 45+ active peer group members means Greg can connect you with the right expert, partner, or peer.

How Strategic CEO Advisory Works

Commitment: One quarter (12 weeks). Focused and intensive by design.
Sessions: 6 biweekly 90-minute deep dive strategy calls via Zoom.
Between calls: Unlimited access to Greg via text, email, or quick calls.
Investment: $5,000–$7,500 per quarter, depending on scope and complexity.
After the quarter: Continue, transition into a Peer Group, or wrap up. No pressure either way.

Let’s Talk About Your Situation

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Frequently Asked Questions

Who is CEO Advisory best for?

Serious B2B SaaS founder-CEOs with $1M-$20M ARR who have urgent strategic challenges and want intensive, focused work with someone who understands their business deeply.

How is this different from the peer groups?

Peer groups give you a long-term community of 8-10 SaaS founder-CEOs working together monthly. Advisory gives you Greg’s undivided attention biweekly, going deep into your specific situation.

What kinds of challenges do advisory clients work on?

Should I hire a VP of Sales or restructure the team? How do I restructure pricing without losing customers? Should I pursue this acquisition opportunity? How do I make the company more valuable over the next 12 months?

How much does it cost?

$5,000-$7,500 per quarter, depending on scope and complexity. Includes 6 biweekly 90-minute sessions and unlimited access to Greg between calls.

Can I continue beyond one quarter?

Yes. Some founders work with Greg for multiple quarters. After each quarter, you and Greg assess whether to continue, transition to a peer group, or wrap up.

How many advisory clients does Greg take at a time?

Greg works with 2-4 advisory clients per quarter. This keeps the work intensive and ensures Greg has the bandwidth to go deep.

I'm not sure if I need advisory or a peer group. What should I do?

Reach out and have a conversation with Greg. He’ll ask about your situation, challenges, and goals, and help you figure out the right path.