Jillian Irizarry Discusses Sales Management in an AI World
The Sales Leaders Operating System™
Release Date: 05/07/2025
Integrating Trust, Systems, and Alignment— Key Themes for Effective Sales Leadership
The Sales Leaders Operating System™
In this special 65th episode, host Matt McDarby recaps the most impactful lessons that have emerged in recent months, reflecting on key recurring themes with a fresh focus: how trust, effective sales systems, and strategic alignment form three core pillars of effective sales leadership and high-performing sales teams. Drawing on insights from conversations with industry expert guests—namely Charles Green, Matt Buchalski, Bruce Wedderburn, Chris Jennings, Jillian Irizarry, John Golden, Corey Schwitz and Dave Levy—Matt outlines how to intentionally build a trust-driven culture, implement...
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Bruce Wedderburn on Embracing Tension in Sales Leadership
The Sales Leaders Operating System™
In today’s episode, host Matt McDarby welcomes Bruce Wedderburn, an incredibly talented sales executive and leader whose career spans roles at Dale Carnegie, Huthwaite, Miller Heiman, Integrity Solutions, and now MindGym, where he serves as SVP of Sales. The conversation is about what it really takes to lead high-performing sales teams in today’s rapidly changing environment. From navigating the daily tensions between accountability and autonomy to the crucial importance of coaching—not just on metrics, but on true value creation—Bruce shares practical advice, real-world stories...
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Jillian Irizarry Discusses Sales Management in an AI World
The Sales Leaders Operating System™
In this episode, host Matt McDarby welcomes Jillian Irizarry, head of specialist sales at Pegasystems. Jillian brings nearly 20 years of experience in software sales and leadership, sharing practical strategies that sales leaders can put to work immediately. Jillian explains how the “4 Ps” framework— Purpose, Picture, Plan, and People—helps teams achieve clarity and results in times of change. You will learn how to adapt your leadership style to fit individual team members, embrace new technologies, and create a culture where teams feel empowered to innovate. Jillian also offers...
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Navigating Sales Systems with Chris Jennings
The Sales Leaders Operating System™
Today, host Matt McDarby sits down with Chris Jennings, an author and seasoned sales trainer with a rich background that spans roles from field sales rep to independent practice owner. With his competitive spirit and experience, Chris shares his perspective on the importance of systems thinking in sales organizations. Sales leaders will appreciate Chris’ discussion on key components of his sales system such as “Go Live” dialogue and leveraging special teams to boost organizational performance. He also explores how clarity in activities and coordinated leadership can drive team success....
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Nurturing A Trust-Driven Sales Culture with Charles Green
The Sales Leaders Operating System™
Today, host Matt McDarby welcomes Charles Green, renowned author of Trust-Based Selling and coauthor of The Trusted Advisor and The Trusted Advisor Fieldbook. Charles shares his wealth of expertise on trust-based selling, providing actionable insights for sales leaders aiming to enhance team performance through trust building. Together with Matt, Charles breaks down the nuances of trust and how personal virtues and institutional values can create a framework for sustainable trust building in organizations. You will learn practical ways to foster strong, trust-filled relationships both...
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Building Cohesion In Revenue Teams with A. Lee Judge
The Sales Leaders Operating System™
In this episode, host Matt McDarby is joined by A. Lee Judge, an experienced executive in digital marketing and founder of Content Monsta. Lee brings a fresh perspective on aligning sales, marketing, and customer success teams to drive results. Lee introduces his CASH system—focusing on communication, alignment, systems, and honesty—as a way to strengthen collaboration and efficiency in revenue-generating teams. You will gain practical insights on the evolving role of sales in the buyer's journey and the importance of data-driven decision-making. With actionable strategies, this episode is...
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Building a Recruitment Culture with Ben Gotkin to Optimize Sales Team Performance
The Sales Leaders Operating System™
In this episode, host Matt McDarby talks with seasoned recruiting expert Ben Gotkin, principal consultant at Recruiting Toolbox. Together, they explore the essential function of talent acquisition and its direct impact on building elite sales teams. Ben highlights the need for a strategic approach to recruiting, focusing on speed and quality in the hiring process. He offers practical advice on the challenges of identifying the right talent and the significance of going beyond surface-level assessments to understand candidates' capabilities, with valuable lessons on avoiding biases, improving...
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Cultivating Trust and Motivation in Sales with Matt Buchalski
The Sales Leaders Operating System™
In today’s episode, host Matt McDarby is joined by Matt Buchalski, a seasoned sales leader who has developed a unique system called "Trust and Motivate," designed to drive success through building trust and inspiring teams. Matt Buchalski has over a decade of leadership experience at companies like HPE and RealPage. In this discussion, he shares his operating rhythm, the critical questions he asks his team and colleagues to ensure clarity and alignment, and the importance he places on training and coaching. You will learn how he manages common challenges such as selfish behavior and...
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Insights On Revenue Leadership with Corey Schwitz and David Levy
The Sales Leaders Operating System™
In this week’s episode, host Matt McDarby dives into the minds of two exceptional founders and leaders: Corey Schwitz, founder of Skydog Ops, and David Levy, co-founder and Chief Business Officer at Aircover. Corey and David bring a wealth of knowledge and experience in building effective revenue systems and leading high-performing teams and will share insights on the importance of building a solid foundation for any organization, hiring the right people, clear communication and prioritization. From early-career experiences rooted in venture capital and tech to running successful businesses...
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How Focus and Alignment Saved An Iconic Brand In Sales with John Golden
The Sales Leaders Operating System™
In this episode, host Matt McDarby welcomes John Golden, an industry veteran with extensive experience in sales, strategy, and marketing. John shares practical insights from his time at notable companies like SmartForce, Skillsoft, and PipelinerCRM. The discussion focuses on the importance of clarity, focus, and alignment within sales teams, using real-world examples from John and Matt’s tenure at Huthwaite, the home of SPIN Selling(™). You will gain actionable advice on effective communication, fostering team alignment, and managing through complexity. This episode offers straightforward...
info_outlineIn this episode, host Matt McDarby welcomes Jillian Irizarry, head of specialist sales at Pegasystems. Jillian brings nearly 20 years of experience in software sales and leadership, sharing practical strategies that sales leaders can put to work immediately.
Jillian explains how the “4 Ps” framework— Purpose, Picture, Plan, and People—helps teams achieve clarity and results in times of change. You will learn how to adapt your leadership style to fit individual team members, embrace new technologies, and create a culture where teams feel empowered to innovate. Jillian also offers insights on breaking the good habits that may be limiting growth.
This episode is a must for sales leaders focused on driving real impact and developing high-performing teams.
Show highlights:
- Listen to Jillian Irizarry’s reflections on the 4 Ps of change management. [03:46]
- How to drive team adoption of leadership frameworks. [05:51]
- How Pega implements new tools using experiential learning. [08:59]
- Tips to encourage innovation to empower the growth of team members. [11:09]
- The power of breaking good habits for reimagined systems and new realities. [13:33]
- What are your personal drivers that can make you a better leader? [19:48]
- Jillian Irizarry’s key mentorship lessons – success leaves clues. [23:34]
- Bonus tip on what to do when you forget someone’s name. [26:47]
- Wisdom to rearchitect your purpose in an AI sales world. [29:03]
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