What you get
Not theory. Operating rhythm.
Every engagement is a weekly 1:1 with Bill – not an associate, not a framework deck. Real-time decisions, honest pushback, and the kind of muscle memory that only comes from someone who’s been in the seat.
01
WEEKLY 1:1 WITH BILL
Scheduled, recurring, and consistently useful. Not occasional check-ins — a true operating rhythm that compounds over time.
02
Decision frameworks
When you’re deciding who to hire, what to cut, or how to structure your leadership team – Bill’s been there. Multiple times.
03
HONEST PUSHBACK
Bill won’t validate a bad plan because you paid him. The value of this engagement is exactly the conversations most advisors avoid.
04
EXECUTION ACCOUNTABILITY
Showing up week over week changes what you ship. Bill tracks commitments and holds the line — in the best possible way.
Who this is for
The hard middle. And the breakout.
Stage 2 — $2M → $20M ARR
You’ve found product-market fit. Now everything else breaks.
- Building a leadership team for the first time
- Navigating rapid or uneven growth
- Fixing the people issues that are slowing you down
- Establishing metrics and operating rhythm
- Managing the board as expectations shift
Stage 3 — $20M → $100M ARR
You're scaling. But the CEO role is changing faster than you are..
- Evolving from operator to organizational leader
- Building and managing a full executive team
- Scaling org structure without breaking culture
- Navigating M&A conversations and late-stage rounds
- Positioning for category leadership
Less than 1% of software startups break $20M ARR. The ones that do almost all share something in common: a CEO who knew what they didn’t know – and found someone who did.
About Bill
He coaches what he’s lived.
Bill’s run four internet and startup companies as CEO, including Conviva, Shopkick, and Turn — with executive stops at Microsoft and Yahoo along the way. Over 30 years, he’s grown organizations from $1M to $110M in revenue, scaled others from $250M to $1B, and built teams from 35 people to 450, with four successful liquidity events. Goldman Sachs named him one of the 100 Most Intriguing Entrepreneurs in 2014, and Ernst & Young tapped him as an Entrepreneur of the Year finalist in both 2012 and 2013.
Now he’s coaching one type of founder: CEOs who are scaling and want to do it right.
The Engagement
Simple by design.
Talk to Bill first
Free trial session
Weekly 1:1 cadence
Stage-matched focus
Get started
One conversation tells you everything.
Free trial session available after your initial call. B2B SaaS CEOs only.