Weekly 1:1 coaching for driven CEOs

The coach who's done it 4 times.

Bill Demas has been a startup CEO four times and scaled companies from zero to $100MM+ ARR. He coaches B2B SaaS founders at the stages most coaches have never seen from the inside.

4xStartup CEO

$0 → $100MM+ARR, firsthand

EY Entrepreneur of the YearFinalist

Goldman Sachs 100Most Intriguing Entrepreneurs

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

No junior intake call. No application form. You talk to Bill directly — he wants to understand where you are, what’s hardest, and whether his working style is a match for yours.

Free trial session

Before you commit to anything, you get a real session — the same 1:1 format you’d get as a paying client. No card required. No obligation. You’ll know within an hour whether this works.

Weekly 1:1 cadence

Ongoing weekly sessions with Bill. Same time, same format, consistent accountability. The rhythm is the point — it’s how the work compounds.

Stage-matched focus

The issues at $5M ARR aren’t the issues at $40M ARR. Bill works from where you actually are — not from a generic CEO playbook.

Get started

One conversation tells you everything.

No commitment. No card. Just a direct conversation with Bill to see if the fit is right – and what working together would look like.

Free trial session available after your initial call. B2B SaaS CEOs only.