GAINING TRACTION: EXPANDING TO $20MM ARR

Bring order to the chaos: Scale with speed, discipline, and a united team.

You’ve found your product-market fit. Now’s the time to focus on leadership, operating rhythm, and efficient growth, and scale from $2MM to $20MM ARR without losing your edge.
Let’s Get Started

STAGE 2 OVERVIEW

Find your focus and gain market traction.

After finding product-market fit, an equally tough challenge begins: scaling from $2MM to $20MM in ARR while building the leadership team, continuing product innovation, and bringing focus to all the possibilities out there. Fewer than 1% of software startups ever get this far — but you can tilt the odds in your favor with the CEO Whisperer playbook from a four-time start-up CEO who’s led companies from this stage to $100MM+ revenue. Bill’s program combines a structured, proven framework with the pragmatic insights that only come from lived startup experience, all delivered in-bite size chunks.

Leverage a focused curriculum tailored to your biggest obstacles, receive regular one-on-one guidance from Bill, and explore a unique interactive portal that helps you drive wins and momentum week-to-week. The program will deliver immediate clarity on your top three priorities with visible results within one quarter.

“A mentor is someone who allows you to see the hope inside yourself.”

– Maya Angelou

“I can’t rate Bill’s coaching and expertise any higher. From working with me as a CEO to counseling my leadership team, Bill’s practical perspective has really helped increase the slope of Transcepta’s growth and valuation curve.”
Ray Parsons CEO, Transcepta
“Bill’s insights consistently helped us overcome obstacles that would have otherwise derailed our progress, making him an invaluable partner in our unprecedented success story. His structured approach to navigating the critical stages from product-market fit to scalability provided exactly the framework we needed to scale Spiky.AI by 10X in just twelve months.”
Burak Aksar Founder, Spiky AI

Is this for you?

A program for those truly committed to excellence

Let’s Get Started
The CEO Whisperer framework is designed for founding and start-up CEOs with early revenue traction, who are ready to:
  • Build or upgrade a leadership team and quickly fix people issues
  • Install lightweight processes and a scalable operating cadence
  • Tighten P&L and metrics while accelerating pipeline and revenue
  • Protect culture while hiring deliberately
  • Use AI as an execution multiplier, not a buzzword
The curriculum provides powerful scaffolding — but real transformation happens through its boutique coaching approach. With fewer than 12 active clients at any time, Bill goes deep with the founders he coaches. You’ll get an approach customized for you, actionable to-do’s, and a partner who has seen it all, scaling multiple start-ups from $0 to $100MM+, ready to share wisdom from decades of leading from the front.

Curriculum

A systematized playbook for accelerating momentum, investing in you as a leader, and driving big wins.

This curriculum is designed to help you sharpen your vision and values, track the metrics that matter, and establish a high-impact operating rhythm. You’ll explore how to optimize your business model, resolve issues quickly, expand your market and put the right people in the right seats. This stage equips you with the tools to leverage AI, build lightweight processes, inspire your people, and fundraise effectively.

Module 1

Building the Foundation

Clarify your vision, strategy, values, and priorities.

Module 2

Growing as a CEO

Map CEO time to your four primary jobs (Strategist, Psychologist, Evangelist, Capital) and rebalance for impact.

Module 3

Finding Growth Levers

Discover ways to accelerate growth.

Module 4, 5, & 6

Measuring Key Metrics, Highlighting Issues, Implementing Processes

Install a simple weekly scorecard with one owner per metric. Establish a 90-day issue list and tackle the most important first. Create lightweight, single-page processes with single-point accountability.

Module 7

Incorporating AI

Embrace AI to run more experiments and create defensible moats.

Module 8

Leading People

Here are a series of insights to help your and your company prosper and enjoy the journey.

Module 9

Effectively Fundraising

Whether you’re bootstrapping or raising, this module will help you build the story and credibility to secure your next round — or sustain without one.

Ready to accelerate
your growth as a leader, gain traction
and build a company on the rise?

Let’s Get Started