How a Multi-Certified Executive Coach Turned One Conversation into a $100K Contract

When Dr. DeBorah Byrd left her corporate role 7 months ago to pursue executive coaching full time, it was a bold leap into new territory.

She wasn’t new to business. In fact, she had already built a thriving accounting and tax practice over two decades.

“Accounting was easy because people always need it,” she said. “But coaching? You have to clearly articulate your offer, your impact, and your value.”

What happened next confirmed she made the right move.

A single conversation over lunch led to her first $100,000 coaching engagement.

And the frameworks she learned through Coach Builder helped make it possible.

“The system provided me with the structure, clarity, and confidence I needed to communicate effectively what I do and how I help,” she said. “Instead of guessing, I had a proven framework that actually works.”

Now, she’s using that same clarity to help her clients reset their strategy, rebuild their leadership systems, and finally run businesses that work—without burning out in the process.

From Finance Expert to Executive Coach

With a doctorate in Psychology and nearly 30 years of experience in finance and strategy, DeBorah has always been someone her clients trusted to bring clarity to complex problems.

She launched her accounting firm over 24 years ago. But as time went on, she realized the conversations were shifting.

“I felt like I needed a couch in my office,” she said. “I was their therapist.”

So DeBorah leaned in.

She got certified as an executive coach and founded The WIN Connection, where she blends leadership coaching, mindset work, and proven business frameworks to help entrepreneurs and teams solve the right problems and grow without burnout.

She’s been coaching now for 15 years.

DeBorah’s doctorate in psychology focused on how stress impacts entrepreneurs, particularly how prayer and mindset influence performance.

That research eventually evolved into the 6 core pillars of her coaching approach: emotional intelligence, financial mastery, strategic vision, communication, spiritual alignment, and marketing.

A Customized Coaching Process That Creates Real Results

DeBorah doesn’t believe in one-size-fits-all solutions.

Every engagement begins with a two-page intake that helps her identify each client’s pain points, motivation, and readiness to change.

“I also want to test, are they expecting me to do all the work?” she says. “Because if there’s no buy-in, I don’t want to work with them.”

From there, she customizes their journey from 90-day accelerators to full-year mentorship programs that include group coaching and one-on-one strategy sessions.

When corporate clients need more, DeBorah builds strategic leadership development programs tailored to their specific pain points.

How Coach Builder Helped Scale Her Impact

Even with years of experience and solid client results, DeBorah found herself rebuilding new tools for every engagement.

It worked, but it wasn’t scalable.

That changed when she joined Coach Builder in 2024.

“I was creating a lot of my own frameworks,” she says. “But when I saw the tools you had … I said, this is going to be amazing.”

Now as a Small Business Flight Plan Certified Coach, StoryBrand Certified Coach, and Full Focus Planner Certified Coach, DeBorah uses ready-made frameworks and tools like the Business Assessment to streamline her client onboarding and increase her impact.

“It gave me more tools in my toolkit,” she explains. “And for my clients, it gave them a starting point.”

Big Win: How One Lunch Led to a 6-Figure Deal

Just 6 months after leaving her corporate job, DeBorah closed her first $100,000 executive coaching engagement.

It started with a simple lunch meeting with a former classmate who now leads HR for a large organization.

“She reached out to me and said, ‘I think I need you,’” DeBorah said. “They wanted her to build a leadership development curriculum, but that wasn’t her lane. I told her, ‘I’ve got it.’”

DeBorah quickly identified the company’s biggest issues. They had a 30% retention problem, no clear communication across teams, and over 30 managers all using different systems.

She used Coach Builder tools to assess the situation, craft a plan, and propose a long-term solution.

“I’m gutting it out and starting over,” she says. “And once the systems are in place, I’ll offer to stay on to maintain them. They still need someone checking in every quarter to make sure everything’s running well.”

It’s a win that not only validated her decision to go full-time with coaching. It also gave her a repeatable blueprint for scaling her business.

It’s a clear example of how her expertise, and the frameworks she now uses, positioned her as the solution a company didn’t even realize they needed.

Relationship-Driven Growth

DeBorah’s client pipeline isn’t built on ads or cold DMs. It’s built on value and service.

She’s part of six networking groups, regularly teaches in business communities, and uses webinars to move people from interest to engagement.

“A lot of my teaching is free because I’m part of the group,” she says. “But then I invite them to a webinar … and that’s where I make my offers.”

She’s also found that collaboration is one of her most effective strategies.

By co-hosting events and teaching alongside others, she’s able to multiply her reach and serve audiences who already trust her partners.

“When you collaborate, your sphere of influence is a lot wider,” she says. “You’re able to help a lot more people.”

What a Week in Her Coaching Business Looks Like

DeBorah runs her week with the same clarity she brings to her clients. Her time is blocked into three major focus areas:
 

 
Even her social media posting is streamlined.

“I can do all 9 platforms within an hour,” she says.

What’s Next for The WIN Connection

DeBorah is fast becoming the go-to consultant for companies looking to fix more than just their performance.

She helps them solve the deeper issues: misalignment, culture, and communication breakdowns.

“They’re trying to blend HR and learning development, but most don’t have the staff or tools,” she says. “That’s where I come in.”

With a fully systemized coaching business, scalable offers, and the clarity to lead with confidence, DeBorah is building a company that wins. All without sacrificing her time, health, or values.

“You don’t need more hustle,” she says. “You need a reset. Let’s win together.”

Takeaways from DeBorah’s Success

If you’re a coach with a strong background but too many custom tools and not enough clarity, DeBorah’s journey offers a proven path forward.

Here’s what she learned so you don’t have to:
 

 
Ready to turn your coaching skills 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.