Episode 5
Runtime: 39:51
February 20th, 2026
In this episode of Crushing It, Jonathan Trimble and Rob Cochran sit down with Kevin Browett, a seasoned fractional CEO and transformation executive whose career spans pharmacy, retail, healthcare, media, and technology-driven organizations . With decades of experience leading turnarounds and scaling complex enterprises, Browett shares what it really takes to walk into chaos—“Legos all over the floor”—and build a high-performing organization from the ground up.
The conversation dives deep into the mechanics of transformation: diagnosing the true product a company delivers, aligning process and technology to support it, and making the hard people decisions that determine whether a business stagnates or accelerates . Browett explains why ego is often the hidden obstacle in executive teams, how over-communication and listening build buy-in, and why winning leaders must give credit away to create loyalty. Through stories from Kmart, healthcare, and private equity environments, he illustrates how trust is earned—not declared—when stepping into legacy cultures resistant to change.
This episode also explores one of leadership’s most difficult truths: sometimes the culture cannot be changed. Browett candidly reflects on moments when persistence becomes counterproductive, and how leaders must discern whether they are building momentum—or eroding themselves against an immovable wall . It’s a rare and honest discussion about knowing when to push harder and when to step away.
The discussion closes with a forward-looking perspective on technology and AI as tools for operational efficiency and smarter decision-making, not replacements for human leadership . For founders, executives, and operators navigating growth, dysfunction, or reinvention, this episode delivers practical insight into building teams that win, cultures that endure, and leadership habits that scale.
What it really takes to lead a business turnaround
How to win over resistant executives without triggering ego battles
Why culture—not strategy—is often the real barrier to growth
The difference between managing performance and leading people
When persistence becomes self-sabotage—and how to know when to walk away
Kevin Browett is a seasoned executive and fractional CEO with more than four decades of experience leading transformation across healthcare, retail, media, and technology-driven organizations. With a foundation in pharmacy and enterprise operations, Kevin has built a reputation for stepping into complex, high-pressure environments and restoring clarity, performance, and growth. His leadership career includes senior roles at major national retailers and large healthcare organizations, where he has overseen multibillion-dollar divisions and driven large-scale operational change.
Throughout his career, Kevin has specialized in business turnarounds, operational excellence, and building high-performance leadership teams. Known for his practical, people-centered approach, he focuses on aligning product, process, technology, and culture to unlock sustainable results. Whether modernizing legacy systems, restructuring executive teams, or guiding acquisitions, Kevin brings a disciplined yet adaptable framework that helps organizations move from chaos to cohesion.
Today, Kevin works as a fractional executive and advisor, partnering with companies across industries to navigate growth, cultural transformation, and strategic reinvention. He is also a leadership writer and mentor, sharing insights drawn from decades of real-world executive experience. His work centers on one core belief: winning teams build winning businesses—and leadership is earned through trust, humility, and execution.
Jon is a former FBI Special Agent and cybersecurity executive whose career focused on intelligence, analytics, and technology development. A graduate of the U.S. Coast Guard Academy, he brings a strategic, systems-level perspective to how leaders understand risk and make decisions in complex environments.
Rob is a former FBI Special Agent who led and supported extensive international cyber investigations involving complex threat actors and cross-border risk. A graduate of the U.S. Military Academy at West Point, he brings an operational, real-world lens to conversations about resilience, accountability, and leadership under pressure.
Together, Jon and Rob bring FBI-honed lessons about risk and resilience to every conversation.
Interested in being a guest on Crushing It?
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