When you start talking about the programmers who have helped shape the modern sound of Top 40 radio, one name that deserves real respect in the conversation is Dylan Sprague. In a format that evolves almost daily—where a song can explode overnight on streaming platforms and disappear just as fast—it takes a very specific skill set to stay ahead of the curve. You have to understand music, audience behavior, and the science of momentum. More importantly, you have to understand the culture surrounding pop music. Sprague has spent much of his career doing exactly that, quietly building a reputation as one of the most respected programmers in the Contemporary Hit Radio format. Today he serves as Senior Vice President of Programming for iHeartMedia in Boston while also helping guide the company’s national CHR strategy. That’s no small assignment when you consider the number of major markets and heritage brands operating under the iHeart umbrella.

 

Sprague’s current home base is the legendary Boston Top 40 powerhouse KISS 108. If you know radio history, you know that KISS 108 isn’t just another station on the dial. For decades it has been one of the most influential CHR stations in America, a brand that has launched artists, hosted massive concerts, and shaped the musical tastes of generations of listeners in New England. Programming a heritage brand like that comes with enormous responsibility. Listeners expect the station to sound fresh while still respecting the history that made it famous in the first place. Under Sprague’s leadership, the station continues to maintain its place as one of the premier Top 40 brands in the country, balancing today’s biggest hits with the kind of personality-driven radio that keeps audiences coming back.

 

Like many great programmers, Sprague’s path to the top didn’t begin in a corner office. It began in the trenches of radio, learning the format from the inside out and working alongside some of the best programmers in the business. One of the stops along the way was Kansas City, where he worked at KMXV-FM, better known to listeners as Mix 93.3. At the time, the station was under the leadership of legendary programmer Jon Zellner, and the building was filled with the kind of energy that makes great radio possible. In fact, many people in the industry still point to that era as one of the strongest periods in the station’s history.

 

I remember those days well. I had the chance to meet Dylan in Kansas City back in the 1990s when he was working under Zellner at Mix 93.3. Anyone who spent time around that station during those years knows what a special run it was. The station was firing on all cylinders—great music flow, strong personalities, and a programming strategy that understood exactly what the audience wanted. Those might have been the best years in the station’s history, and Sprague was part of the team helping make it happen. Even then you could tell he had the instincts of someone who understood the bigger picture of radio programming.

 

As his career progressed, Sprague continued sharpening those instincts and expanding his influence within the CHR format. His ability to analyze audience behavior, evaluate music trends, and coach talent made him a natural fit for leadership roles. Eventually that path led him to Boston and one of the most iconic stations in Top 40 radio. At KISS 108 he stepped into a position that has historically been held by some of the most respected programmers in the industry. Carrying that torch requires both confidence and discipline, because the expectations are high and the competition in a major market like Boston is relentless.

 

At the same time, Sprague’s responsibilities grew beyond a single station. Within iHeartMedia he became a key voice in the company’s corporate programming structure, helping shape strategy for CHR stations across the country. Serving as Senior Vice President of Corporate CHR Programming means evaluating music, guiding programmers in multiple markets, and helping ensure that the format continues evolving in a way that connects with today’s listeners. It’s a role that blends creative instincts with analytics and long-term planning—skills that only come with years of experience inside the format.

One thing that makes Top 40 radio unique is the speed at which it moves. Songs rise and fall quickly, artists come and go, and audience expectations change with every generation. Successful programmers have to anticipate those shifts rather than simply react to them. Sprague has shown an ability to stay ahead of those trends while maintaining the core fundamentals that make great CHR radio work: tight music clocks, compelling personalities, and promotions that make listeners feel like they’re part of something bigger than just a playlist.

 

Another part of Sprague’s legacy is the mentorship that happens behind the scenes. Corporate programming roles often involve helping younger programmers find their voice and understand how to balance creativity with strategy. Radio has always been a business where knowledge gets passed from one generation to the next, and people who have climbed the ladder themselves tend to be the best teachers. By helping guide programmers across multiple markets, Sprague plays a role in shaping the next wave of Top 40 leadership.

 

From Kansas City to Boston and now across the national CHR landscape, Sprague’s career reflects a steady climb built on knowledge of the format and respect for the audience. He’s part of a generation of programmers who grew up studying the great Top 40 stations of the past and then found ways to adapt those lessons to the digital age of streaming, social media, and rapidly shifting music consumption habits.

 

Now let me bring it back to the Just Plain Steve perspective for a moment, because radio is a relationship business. You meet people along the way, sometimes early in their careers, and years later you look up and realize they’ve become one of the format’s major leaders. That’s the case with Dylan Sprague. Seeing him now guiding one of the most famous Top 40 stations in America and helping shape the CHR strategy for iHeartMedia says a lot about the path he’s taken since those Kansas City days.

The truth is, Top 40 radio has always been powered by programmers who can hear the future before everyone else does. They’re part music fan, part strategist, and part showman. When you find someone who can balance all three, you’re looking at a real power player in the format.

 

That’s why when the conversation turns to Top 40 Power Players — Past and Present, Dylan Sprague belongs on that list. From the halls of Mix 93.3 in Kansas City to the studios of KISS 108 in Boston and the national programming table at iHeartMedia, his career tells the story of a programmer who understands both the history of Top 40 and the direction it’s heading next.

And from where I’m sitting, that’s about as Just Plain Steve as it gets.