The Executive Leadership Coach Bringing a Fortune 500 Mindset to Small Business Strategy

Craig Anderson spent decades managing national sales teams at giants like JPMorgan Chase and Sallie Mae. He thrived in high-pressure environments, closing million-dollar deals in the student loan industry.

His expertise was proven, his track record spoke for itself.

But when it came to building his own coaching practice?

Suddenly everything he thought he knew about business felt uncertain.

Craig knew he had valuable knowledge to share. He already had a business certification and understood the importance of frameworks from his corporate days.

So the transition to coaching seemed straightforward…

Until he actually tried to do it.

The Corporate-to-Coach Challenge

Craig was an experienced executive with a strong network. He assumed building a coaching practice would be simple.
 

 
“My mistake was thinking this was just going to be making a couple of phone calls, getting people to work with me, it was going to be really easy. You just think I’m going to be this independent coach and stuff’s going to happen, it’ll be fine.”

But Craig quickly discovered two major obstacles that nearly every corporate executive faces when starting a coaching practice:

1. The Confidence Crisis
“The hardest part was selling yourself. When you have been in sales all your life, it’s a very different thing when you start selling yourself. That hits a different part of you.”

2. The Customization Trap
Without a clear product structure, Craig found himself customizing everything for every client, making sales conversations longer and pricing inconsistent. “I was just customizing all over the place.”

The Coach Builder Breakthrough

When Craig joined Coach Builder, these things changed everything for his business:

✅ Clear product structure
For the first time, Craig had a defined product ladder instead of customizing everything for each client. This revelation made his sales conversations faster and more confident because both he and his prospects knew exactly what they would be getting.

✅ Intentional business building
Coach Builder taught Craig that successful coaching practices require deliberate planning and structure. Rather than hoping things would “just work out,” he learned to think through his offerings and have a clear execution plan before launching anything new.

✅ Peer Support
The small group coaching sessions provided Craig with something he didn’t realize he desperately needed: other coaches going through similar challenges. Having a place to talk through deal flow and business decisions with peers became invaluable for his growth.

“It’s the accountability of having people who are checking in and who are also pursuing the same things. That’s what gave me confidence.” –Craig Anderson

Craig’s Wake-Up Call

Before joining Coach Builder, Craig had an eye-opening experience that showed him just how much he was undervaluing his expertise.

He had worked with a client, implementing his strategic framework in a single day for $2,500.

When the same client called back during the COVID year wanting him to return, Craig was hesitant about traveling.

Almost as a test, he quoted $10,000 for a day and a half of work. 4 times his original rate.

“They didn’t even blink,” he said.

That’s a 400% price increase with the same client for essentially the same work.

This experience taught Craig that he had been dramatically undercharging based on his own limited view of his value, and that clients would gladly pay premium rates for real transformation.

It was a crucial lesson that primed him for the systematic approach he would later learn through Coach Builder.

The Results Speak for Themselves

Craig’s most powerful client success story involves a company he’s worked with for over 5 years, demonstrating the long-term impact of his strategic planning approach.

When Craig first sat down with this CEO to build their 5-year business plan, they created what he describes as an “aggressive” growth strategy.

It was so ambitious that when they presented it to the leadership team, everyone thought the CEO was “absolutely insane.” The targets seemed unachievable, too aggressive to ever reach.

But Craig’s methodology was different.

Instead of just setting a big goal and hoping for the best, he worked backwards from that 5-year vision. Together, they mapped out exactly where the company needed to be at the end of year 1, year 2, and year 3, creating a step-by-step roadmap with clear milestones.

Then came the discipline: monthly business reviews to track progress, annual strategic planning sessions to adjust course, and consistent focus on the priorities that would drive results. Year after year, the company did the work and stayed on track.

The result?

After 5 years, they had achieved 98% of those “impossible” targets that everyone had initially dismissed.

When it came time to plan the next 5 years, something remarkable had happened.

The entire leadership team’s mindset had fundamentally shifted.

As Craig explains:

“The whole vibe was different because everybody realized if we put this down in writing, we focus on it, we revisit it, we do this one year at a time, we are going to be able to achieve this goal.”

They had transformed from skeptics into believers—not in magic, but in the power of systematic planning, consistent execution, and disciplined follow-through.

This client relationship exemplifies Craig’s approach: building long-term partnerships that create lasting transformation through proven frameworks and accountability.

Craig’s Blueprint for Scaling

Today, Craig operates a sophisticated coaching practice with 2 distinct service levels:

Enterprise Level: Three-day strategic planning retreats for larger companies, followed by ongoing monthly business reviews and framework implementation—relationships that last for years.

Group Coaching: Expanding from 1:1 to group programs implementing proven frameworks like Small Business Flight Plan, creating accountability through peer groups.

“What I’ve really found over the last five years is there’s only so much of me to go around. I can only charge so much to do one-to-ones and I only have so much time. For smaller businesses, I can come in on a much more accommodating price point, help a lot more people, and not make myself crazy.”

Key Takeaways from Craig’s Success

If you’re sitting in a corporate office right now wondering if you could make it as a coach, Craig’s story should give you hope and a roadmap. Here’s what he learned the hard way so you don’t have to:

And thanks to Coach Builder, she’s doing it with a system that works, a community that inspires her, and a growing toolkit of frameworks that help her clients experience real transformation.
 

 
Ready to turn your expertise into a business that works? Coach Builder provides the frameworks, structure, and community support to transform your knowledge into a scalable coaching business. Schedule a call.