In this episode of The KeyHire Small Business Podcast, host Corey Harlock sits down with Charles Fry, Founder and CEO of Codexitos, to tackle one of the most challenging transitions for small business owners: moving from founder-driven sales to building a professional sales organization.

Charles has been in technology since before the internet took shape, founding and growing multiple companies over the decades. With deep experience in scaling businesses, he shares the real-world lessons he’s learned about letting go of being the “only salesperson” and building a sustainable sales team that drives growth.

Together, Corey and Charles dive into:

• Why so many businesses rely on the owner as the primary salesperson—and why that creates a ceiling for growth.
• Why your first sales hire is the most critical and must set the pattern for future hires.
• The danger of bringing on a “sales manager” too early when what you really need is a producer.
• The importance of defining a sales style and methodology that reflects the founder’s vision before expanding the team.

Charles introduces his framework of three phases for founders transitioning out of being the sole salesperson:

1. Zero to One – Hiring your first professional salesperson who mirrors the sales style you want replicated.
2. One to Few – Expanding the team in a way that avoids chaos from conflicting approaches and ensures consistency.
3. Scaling Up – When a larger sales team requires true sales management (though that’s a topic for another day).

Throughout the conversation, Charles emphasizes the nuances of leadership in sales: balancing the founder’s natural ability to “close deals” with the need to empower a team, maintaining patience with new hires as they learn, and putting systems in place to measure performance. He stresses the value of having a clear sales methodology—whether Challenger, SPIN, or another approach—so everyone is speaking the same language and working from the same playbook.

As a mentor once told him, the role of the CEO is ultimately to be the “Cash Extraction Officer.” Charles explains how founders can best serve as closers—brought in for the final inning when their authority and vision matter most—while the sales team does the heavy lifting of qualification and relationship building.

For business owners feeling trapped as the sole driver of revenue, Charles provides actionable steps:

1. Define the sales model and methodology that represents your business.
2. Engage outside help to objectively profile and vet your first hire.
3. Have candid, direct conversations with candidates and hires.
4. Establish clear timelines and budgets for success based on your industry’s sales cycle.

If you’ve been struggling to step out of the salesperson role—or if you’ve felt the frustration of bad hires, inconsistent results, or being the “rate limiter” on growth—this episode is packed with strategies to help you break free from founder-led sales and build a scalable, repeatable sales engine.

Send us a text

KeyHire Solutions helps small business owners scale smarter, not harder. From hiring the right talent to building systems that work, we give you the strategies and support to grow your business without burning out.

Learn More at www.KeyHire.Solutions

Listen on: Apple Podcasts Spotify