Steve Caton Shares When to Sell, When to Coach, and When to Hire: Strategic Sales Management That Drives Growth

Two Tall Guys Talking Sales

In this powerful episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey are joined once again by Steve Caton, CEO of Altezza Solutions, for a thought-provoking conversation that zeroes in on one of the toughest decisions in sales leadership: when to sell, when to coach, and when to hire. Whether you’re a business owner, VP of Sales, or a player-coach juggling a quota and a team, this episode brings clarity to the strategic inflection point where growth hinges on letting go. With frank discussion, lived experience, and tactical advice, Kevin, Sean, and Steve guide you through the complex terrain of sales management, revenue generation, and scaling your team without sacrificing results.

Key Topics Discussed:

• [00:01:58] The pros and cons of player-coach sales roles, and why this model often fails without intentional strategy

• [00:05:34] How to create a psychologically safe sales environment where learning from failure drives sales success

• [00:07:11] Steve Caton’s personal transition from sales operator to CEO—and how it triggered exponential business growth

• [00:09:20] The difference between hiring to "swim faster" and hiring to scale—how business acumen guides the decision

• [00:13:00] Real-world use cases for fractional sales roles to test new markets or offerings without disrupting core revenue streams

Key Quotes:

• Kevin Lawson [00:04:57]: “Sometimes you have to let people fail. You can’t push them into failure, but you do have to give them the room to learn. The challenge is, as a leader, you're still accountable for that failure.”

• Sean O’Shaughnessey [00:04:01]: “It’s much easier to do one thing well. Let great salespeople sell and great managers manage—don’t dilute either role.”

• Steve Caton [00:08:30]: “I made the decision to stop selling before I could afford it. Why? Because I knew the payoff would be big. Sometimes, you just have to invest in your business to grow.”

• Kevin Lawson [00:11:34]: “A sales process with control metrics, plus intentional feedback loops, informs exactly how and where your business should grow.”

Additional Resources:

• Steve Caton https://www.linkedin.com/in/scaton/

• Altezza Solutions: www.atezzasolutions.com

• Book Mentioned: Great by Choice by Jim Collins (for the “bullets before cannonballs” strategy) https://a.co/d/1j6R6vt

A Significant Actionable Item from this Podcast: Reevaluate your team structure and decide: are you scaling or surviving? If you're a business owner or sales leader wearing multiple hats, it's time to assess whether you're enabling growth or capping it. Consider where your time is most valuable—rainmaking, coaching, or closing—and invest in building the right team around you. Start with fractional or part-time hires to test new roles or markets, then double down when the data supports it.

Closing Summary:This episode cuts through the noise around sales team building with a refreshing mix of vulnerability, experience, and strategic depth. Whether you’re weighing your first sales hire or deciding to step out of the player-coach role, Two Tall Guys Talking Sales delivers real-world sales strategies that help you align your messaging, sales processes, and revenue management decisions with long-term growth. Don’t miss this one—it’s 15 minutes of business-building insight that could change the trajectory of your sales organization. Hit play now and discover how letting go might be the smartest way to grow.

To understand if your company is doing a great job in sales, take this quick and easy assessment: https://newsales.expert/b2b-sales-capability-assessment/

You can reach out to Sean at New Sales Expert, LLC - [email protected] - https://www.linkedin.com/in/soshaughnessey/

You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - [email protected] - https://www.linkedin.com/in/kwlawson/

You can book time on Kevin's calendar at https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin

You can book time on Sean's calendar at http://newsales.expert/sean-oshaughnessey-calendar/