Why Pricing Might Be the Best Path to CEO You've Never Considered with Ryan Walter

What if the pricing function isn't just a specialty discipline—but one of the best training grounds for future CEOs?

Ryan Walter, Partner at Jennings Executive Search and author of The Pricing Talent Playbook, joins Mark to explore the evolution of pricing careers, what separates great pricing leaders from average ones, and why pricing may soon become a recognized pathway to the CEO role. Ryan draws on his experience recruiting pricing talent and leading pricing teams across retail, manufacturing, data products, and industrial businesses.

If you're building a pricing career, hiring pricing talent, or wondering how AI is reshaping the profession, this episode offers a glimpse into where pricing is headed next.

 

Why you have to check out today’s podcast:

• Discover why pricing may become a legitimate path to the CEO role.
• Learn why pricing transformations often fail despite strong strategy.
• Understand how AI is changing pricing talent expectations and why curiosity may now be more important than technical expertise alone.

 

"My prediction is that the pricing function is going to end up being a path to CEO."

— Ryan Walter

 

Topics Covered:

01:00 – From Professional Musician to Pricing Leader. Learn why the skills required in professional music translated surprisingly well into pricing leadership.

03:05 – The Rare Combination Every Great Pricing Professional Needs. Why pricing success requires both IQ and EQ—the ability to work with complex data while influencing executives, sales teams, and non-technical stakeholders. Ryan explains why finding both traits in one person is surprisingly rare.

05:05 – The EQ Problem Pricing Professionals Must Solve. Mark and Ryan discuss why being right isn't enough. Learn how great pricing leaders simplify complexity, build trust, and communicate insights in ways that drive action instead of resistance.

06:50 – Why Ryan Wrote The Pricing Talent Playbook. Ryan explains the motivation behind his new book and why pricing leaders need more guidance on talent, team building, interviewing, and career development—not just pricing models and strategy.

09:20 – The Hidden Reason Pricing Transformations Fail. A fascinating hiring story reveals how a successful pricing leader was undermined when executive priorities shifted. Learn why organizational support often matters more than technical pricing expertise.

11:30 – What AI Is Changing About Pricing Right Now. Ryan shares examples of pricing leaders using AI to perform customer profitability analysis, strategic planning, and complex investigations in hours instead of weeks. The discussion moves beyond productivity into AI as a strategic thought partner.

14:30 – The New Hiring Question Every Pricing Candidate Should Expect. More companies are now evaluating AI readiness during interviews. Ryan explains what hiring managers actually want to hear—and why curiosity matters more than having the perfect answer.

17:00 – Why Pricing Professionals Change Jobs More Often. Many pricing leaders thrive on building functions, driving change, and solving messy problems. Ryan explains why some professionals leave after creating momentum—and why that's often a feature, not a flaw.

19:15 – The Two Pricing Archetypes. Are you the builder or the operator? Ryan breaks down the two common pricing career paths: the change agent who loves creating order from chaos and the operator who excels at maintaining and evolving mature pricing functions.

22:00 – Why Pricing Could Become a Path to CEO. The episode's biggest idea. Ryan explains why pricing professionals gain unusually broad exposure to strategy, systems, finance, customers, and operations—and why that experience mirrors many responsibilities of a CEO.

 

Key Takeaways:

[on pricing talent and skills ] "You need to be able to do the math and deal with the data and build models and figure out how systems work. But you also need to speak to non-technical folks in a way that they understand what your model is doing." – Ryan Walter

[on pricing talent and skills ] "It's not just how to do math. It's helping as a thought partner to come up with [pricing] strategy." – Ryan Walter

[Communication & Influence ] "You can't tell the sales leader about the R-squared. You have to simplify that down." – Ryan Walter

 

People & Resources Mentioned:

• Jennings Executive Search – Executive search firm specializing in pricing and commercial leadership recruitment.
• The Pricing Talent Playbook – Ryan's new book focused on pricing talent, career development, and building pricing organizations.

 

Connect with Ryan Walter:

• LinkedIn: https://www.linkedin.com/in/ryan-walter3141/ 
• Email: [e-mail]

 

Connect with Mark Stiving:

• LinkedIn: https://www.linkedin.com/in/stiving/
• Email: [e-mail]