BREAKING OUT: ESTABLISHING CATEGORY LEADERSHIP

Breaking through $100MM ARR and building a global category leader.

At this stage, it’s a thrilling and crazy time. You’re managing complexity: new geographies, second product lines, M&A, Board dynamics, and leading old-timers and newcomers.  We’ll focus on the signal, not the noise, by impacting the activity that really matters, while keeping the soul of your company intact.

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STAGE 3 OVERVIEW

Break from the pack.

After gaining traction, the next challenge is to grow to $100MM in ARR and establish your company as a category leader nationally and then globally. Many startups mysteriously stall at the $40MM mark, but you can break through thanks to unmatched strategic insights from the CEO Whisperer, who has overcome this slowdown multiple times as a four-time start-up CEO.

With the Breaking Out curriculum, you’ll get access to a deeper playbook that addresses second-act innovation, maintaining and growing your culture as the business takes off, refining your organizational design, along with a pragmatic operating model to sustain speed, quality, and accountability at scale. From maximizing product, sales, and marketing performance to managing your Board and investor relationships, this stage equips you to accelerate growth and enhance your personal and industry leadership.

“No man is more unhappy than he who never faces adversity. For he is not permitted to prove himself”

– Seneca

“Bill’s deep leadership experience in scaling four start-ups coupled with his approachability and supportive nature has been an absolute difference maker to me and valuation-driver for PitchIt.  He has also played a role in keeping the rest of the board members’ interests aligned with the goals of our startup, constantly providing context to help everyone understand each other’s incentives.”

Paul Kleen Founder/CEO, PitchIt

“Bill’s frameworks are a masterclass in scaling with clarity. His materials don’t just advise—they architect a strategic path from idea to impact. For any B2B SaaS leader serious about breaking through the chaos of early growth and unlocking real traction, Bill’s insights are the competitive advantage.”

Mike Liu CEO, FreeFuse

Is this for you?

My program is meant for those truly committed to excellence.

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The CEO Whisperer framework is designed for CEOs looking into fresh growth vectors, who are ready to:
  • Push past plateau points
  • Mature the executive team and org structure while sustaining culture
  • Level up capital strategy, Board construction, and M&A opportunities
  • Improve operating margin, while accelerating topline
  • Deciding where AI agents, automation, and process power unlock productivity
The curriculum provides powerful scaffolding — but real transformation happens through my boutique coaching. With fewer than 12 active clients at any time, Bill goes deep with the founders he coaches. You’ll get a personal health check-in, actionable to-do’s, and sessions designed for you and your start-up to breakthrough.

CURRICULUM

Category momentum: compounding growth through new vectors, a stronger executive bench, and scalable culture.

This curriculum is designed to help you drive what really matters so you and your company ultimately win. You’ll finish the program equipped with tools for top-to-bottom team alignment, faster decision-making, and noticeably improved results within one quarter.

Module 1

Building the Foundation

Clarify your vision, mission, strategy, values, company culture and Top 3 priorities

MODULE 2

The CEO

Become excellent in your four primary jobs as CEO – Chief Strategist, Chief Psychologist, Chief Evangelist and Chief of Capital.

Module 3

Growth Levers

Discover ways to accelerate growth. Apply Hemler’s Seven Powers to attain differentiable advantage. How to think about M&A.

MODULES 4, 5 & 6

Metrics, Issues, Processes

Create lightweight processes with single-point accountability.

Module 7

AI

Use AI to run more experiments faster and build your business around 4 defensible moats against the hyper-scalers.

MODULE 8

People

Building your organization to fit your growth profile; putting the right people in the right seats; keeping your culture thriving during growth and downturns.

Module 9

Fundraising

Build your story for your next round of investment, strategies on who to target and how to maintain control.

You’ve built momentum.
Now build a category leader.

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