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Jillian Irizarry Discusses Sales Management in an AI World

The Sales Leaders Operating System™

Release Date: 05/07/2025

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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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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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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 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]

Book a call with Matt using this link: https://calendly.com/mattmcdarby/30min 

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