Kevin LeGrett has been inside the machinery of American radio at its most powerful scale — running the West Coast as Division President for iHeartMedia, leading Los Angeles as the nation’s top-billing cluster for a decade, building iHeart Sports, and overseeing political sales strategy, plus previous high-level posts at Citadel and Infinity.
He has seen, from the inside, exactly what massive organizations can do and exactly where they stall. So when Beasley Media Group came calling earlier this year with a newly created Chief Business Officer role, the question wasn’t whether LeGrett knew the industry. It was whether the industry was finally ready for what he wanted to build.
LeGrett sat down with Radio Ink to answer that question.
Radio Ink: This is a brand-new role for Beasley. What was it that brought you back to radio and into a company that, by its own admission, has had a difficult few years?
LeGrett: To be perfectly frank, I wasn’t sure a year ago at this time I would have been in the media business. I worked for iHeart through 2024 and then in a consultant role for them in 2025. During that time, I spent a lot of time with other industries and other verticals, including a lot of time in the AI area, which was really educational and gave me a great foundation for whatever industry I went into afterwards.
I didn’t come to Beasley because I needed a seat. I came here because of the canvas. When Brian and Caroline called me, and digging into it with them—there’s excitement here.
Caroline runs this company with a rare combination of financial discipline and genuine belief in the medium. She’s one of the most respected voices in our industry for a reason. She and Brian weren’t asking me to maintain something—and I just don’t want to maintain something. They were asking me to build something.
The newly created Chief Business Officer seat was built to unify strategy, revenue, programming, finance, and execution under one clear discipline. The excitement for me was that it’s inside a company nimble enough to actually move.
I’ve seen exactly what massive scale can do and exactly where it gets stuck. At the giants, brilliant ideas too often die in a national mandate that never translates to the local street. Beasley is big enough to have world-class tools and attribution, but small enough to turn the ship in one afternoon when a partner in Charlotte or Tampa needs to win their specific zip code.
I’ve always believed that radio’s challenge was never relevance. The audience has never left. It was execution and alignment. This was a chance to take everything I’d learned running some of the largest clusters in America and apply it somewhere I could actually build fast—with an owner who wants to compete and backs her team to do it. I’ve spent my career inside the big machine. This is my chance to build something smarter and faster.
Radio Ink: Your reference to Beasley’s new “war room cadence” during your first earnings call with the company was particularly striking. What exactly does that mean?
LeGrett: The war room is a rhythm of accountability. It exists because the old model was too slow. Waiting a month for a ratings book to grade your performance is no way to run a modern media business. We run a tight weekly cadence built on shared real-time data—pacing, sales velocity, digital engagement, podcast impressions and downloads, and at-risk revenue. In these meetings, the entire leadership team looks at the same scorecard at the same time. And because we’re all together, we make decisions fast.
Culturally, it does two things I deeply care about. First, it kills the silo mentality. Digital, broadcast, events, programming, and finance are all in the same room solving the problem, which is the only way a 360-degree strategy actually works.
Second, it pushes power to the leaders closest to the action. They bring the market truth, and we strip away the corporate noise and resource the winners—the people who actually deliver month in and month out, quarter in and quarter out. The strategy flows naturally from the cadence. When everyone sees the same numbers every week, you stop debating opinions and start managing outcomes. That’s the difference between a reporting culture and a performance culture. It’s how you build trust and speed at the same time.
My job as CBO is to protect that rhythm and make sure it drives decisions, not just dashboards.
Radio Ink: When building this rhythm, where did you decide to start?
LeGrett: Like anything—whether leading a sports team or a business unit—it all starts with alignment, because everything compounds off of it. The relevance debate has already been settled by the data. Radio reaches 93 percent of US adults every month and 89 percent of the hard-to-reach 18-to-34 audience monthly. The audience never left.
So I went straight at the wall between the digital seller and the broadcast seller and started building one unified 360-degree marketing force pointed in a single direction—audience-based selling versus a product-based sales approach. Execution came next: giving those aligned teams the modern tools they need, leaning into technology and AI, along with a training and certification program, so they can actually deliver the integrated solutions we’re promising our prospects and clients. Closed-loop attribution, first-party data, real campaign optimization.
Once alignment and execution are in place, monetization takes care of itself, because a trained and unified team selling outcomes converts at a far higher rate than a fragmented one selling spots on faith and very little strategy. The sequence is the whole game. If you chase monetization before you fix the alignment and execution, you pile pressure onto a broken system and burn out your best people.
Fix the foundation first—one team with the right tools and real accountability—and the revenue flows and keeps flowing. I’ve run this play at scale before, and it works.
Radio Ink: Was there any particular place of inspiration for this model?
LeGrett: I’ll give credit where it’s due. I’ve been very fortunate to have learned from some of the giants of media and broadcasting throughout my career. When people have asked me who my role model is, I’ve always said, tongue in cheek, it’s Frankenstein—because he’s the combination of many people and many assets. I’ve had the privilege of learning this business from some of the very best: from Don Bouloukos and Mel Karmazin to Farid Suleman and Judy Ellis, to John Hogan, Jeff Howard, and Bob Pittman. And today I get to learn from Caroline.
Tomorrow, the conversation continues: LeGrett gets specific on what it will take to change the way radio sells itself to national advertisers, what he found when he walked into Beasley’s markets for the first time, and what a real reset looks like by December 31st.
