How To Succeed on the Road to Senior Leadership

In this episode, Mike Crandall sits down with Ryan Jacob, President of GRA Services, about succeeding on the road to senior leadership using Sandler’s Success Triangle: Attitude, Behavior, and Technique. Ryan describes developing optimism, curiosity, and emotional discipline; practicing consistent follow-through and data-driven processes; and applying Sandler’s techniques like Up-Front Contracts and Reversing—first as a sales student and contributor, then as a Leader.

As President, Ryan reframes these tools internally to sell change, align expectations, reduce defensiveness, and build trust, emphasizing that teams feel leadership’s emotions and follow consistent actions. He highlights GRA Services’ rapid growth supporting utility infrastructure with a pole-setting foam product, and credits the Sandler communities’ shared language for accelerating execution and decision-making.

Core takeaways from this episode: Maintain an “Abundance Mindset” with emotional discipline. Model consistent behaviors to shape culture. And use clear Up-Front Contracts to eliminate confusion and resentment.

 

Chapter 1: Opening and Podcast Framework

00:00:02 – 00:00:39 Dave Matson introduces the “How to Succeed” podcast and its focus on the Success Triangle: attitudes, behaviors, and techniques. He sets the expectation to explore how top performers think and act to reach and maintain success.

Chapter 2: Meet the Host and Guest; Topic Setup

00:00:39 – 00:02:06 Host Mike Crandall introduces himself and his guest, Ryan Jacob, president of Gray Services. The episode’s theme is succeeding on the road to senior leadership through BAT (Behavior, Attitude, Technique), framed by Ryan’s long journey from sales student to company president.

Chapter 3: Ryan’s Early Sales Roots and Mentorship

00:02:06 – 00:02:59 Ryan shares his background in professional selling and his connection with Mike through UCO’s collegiate sales program. He explains how early mentorship and applying learned concepts at work led to tangible results and an enduring professional relationship.

Chapter 4: Attitude Foundations as a Sales Student

00:02:59 – 00:05:27 Ryan emphasizes embracing struggle, maintaining optimism, and staying calm and curious. He highlights asking strong questions, using disqualification when appropriate, and building momentum through repeated effort as core attitude differentiators.

Chapter 5: Behaviors that Create Opportunity

00:05:27 – 00:07:05 Consistency and follow-through become Ryan’s standout behaviors, often winning opportunities others missed. He recounts showing up, honoring commitments, and leveraging initiative to access professional circles despite student constraints.

Chapter 6: Techniques that Accelerate Early Success

00:07:05 – 00:09:19 Key techniques include strong upfront contracts, reversing and negative reversing to deepen discovery, and sorting versus selling. Ryan stresses asking hard questions calmly and iterating relentlessly to internalize and scale effective methods.

Chapter 7: Attitude as a Top Individual Contributor

00:09:19 – 00:11:28 Curiosity lowers defensiveness and fosters honest conversations, contrasted with pushy selling stereotypes. He underscores the importance of “not needing the sale” to avoid “commission breath,” particularly when pipeline is thin.

Chapter 8: High-Value Behaviors in Sales Execution

00:11:28 – 00:13:21 Ryan details embracing discomfort, intelligent prospecting, and a repeatable system mindset. He uses data-driven reflection to refine processes, evaluate outcomes, and adapt continuously to improve win rates.

Chapter 9: Techniques for Complex, Long Cycles

00:13:21 – 00:14:51 Professional sorting becomes critical in long enterprise cycles, building relationships far ahead of renewal or change windows. Strategic timing and positioning are essential to influence multi-year opportunities.

Chapter 10: Transition to Senior Leadership and Gray Services Overview

00:14:51 – 00:17:18 Ryan describes Gray Services’ two-part foam solution for faster utility pole setting, enabling grid expansion amid rising electricity demand. He outlines the company’s 1994 origins, rapid scaling, automation plans, and facility expansion.

Chapter 11: Leadership Attitude Under Pressure

00:17:18 – 00:18:59 Leadership amplifies BAT principles: actions over words, leading by example, and using action to drive emotion. Responsibility for livelihoods raises the stakes for mindset discipline and consistency.

Chapter 12: Selling Change Internally

00:18:59 – 00:21:12 Ryan discusses projecting steady, positive energy as teams feel leadership’s emotions. He uses upfront contracts and curiosity to lower defensiveness, invite collaboration, and co-create change with long-tenured staff wary of disruption.

Chapter 13: Behavior Consistency Builds Trust

00:21:12 – 00:23:16 Doing what you say you’ll do establishes credibility across the organization. Ryan highlights modeling small actions, like picking up trash, to signal standards and align culture amid rapid transformation.

Chapter 14: Leadership Techniques for Clarity and Accountability

00:23:16 – 00:25:58 Upfront contracts shift from sales to internal alignment, clarifying goals, timelines, and expectations to reduce confusion and resentment. Structure makes hard conversations fairer and more consistent, while reversing elicits candid input from those closest to the work.

Chapter 15: Community, Faith, and the Power of a Shared Language

00:25:58 – 00:31:08 Ryan shares how faith, patience, and unforeseen succession accelerated his leadership path. He leveraged the Sandler community for trusted expertise, enabling faster decisions and execution by “cutting through the fluff” with a common framework.

Chapter 16: Final Insights on BAT for Senior Leadership

00:31:08 – 00:37:08 Ryan’s closing guidance: cultivate emotional discipline and an abundance mindset (attitude), recognize that culture mirrors leadership habits and consistency (behavior), and use clear upfront contracts to set expectations and reduce confusion (technique). He credits Sandler’s systems, community, and common language for sustained growth.

Chapter 17: Close and Credits

00:37:08 – end Mike thanks Ryan and wraps the episode, reinforcing the theme of succeeding on the road to senior leadership. The podcast credits acknowledge Sandler Systems, LLC and direct listeners to local trainers or the website for more information.