The Industry According To: Keith Dakin, Connoisseur Media

Thank you for checking out The Industry According To. Every Tuesday, we speak with a different expert or leader from the music industry — label executives, artist managers, programmers, talent, artists, consultants, and beyond. To appear as a future guest, email Keith Blackbox Group at keithblackboxgroup@gmail.com.

Today we sit down with one of the most versatile and respected programmers in modern radio. He is a leader who has worked inside small, fast-moving companies and larger, multi-market organizations. At these organizations, scale and culture truly matter. Keith Dakin has spent over 25 years in the industry, working at several broadcasting companies, including a high-impact run programming the legendary WFNX/Boston. Throughout his career, his stations have been dominant. Furthermore, they have been nominated for more than 10 Marconi awards. Currently, Keith is the SVP of Programming for Connoisseur Media. He oversees a wide mix of formats, talent, digital strategy, and brand development at over 200 stations across nearly 50 markets.

So, let’s dive in.

*Editor’s Note: Answers have been edited for clarity and length.*

Hundreds of Stations Overnight

Keith Cunningham: You go to sleep responsible for a dozen stations. You wake up the next morning responsible for over 200. Many are in markets you’ve never been to. What’s your process for getting to know that many brands quickly? How do you decide which ones need attention first?

Keith Dakin: Ha! It’s been a wild year, for sure. Step one was to figure out who’s who and what’s what. Most importantly, I needed to determine where exactly Saginaw, Michigan is located. Once I finished that task, the summer of 2025 was a summer of a thousand phone calls. I tried to meet, via Zoom, every single PD, OM, and morning show we had. Afterwards, I have, basically once a month, tried to hit one or two markets. I’m writing this from the plane leaving the Bay.

What we found from the start was that Alpha had really cut back these markets. Indeed, OMs and PDs were desperately needed. We started to fill those holes. Ross MacLeod in Portland was our first hire. One of our biggest markets needed a leader. Moreover, he was the perfect fit.

We moved from market to market doing the same thing. Specifically, we targeted San Jose, Palm Springs, Dayton, and Long Island. We adjusted stations, hired people, and tried to focus on our mission. Our mission was to get back to doing what radio does right — connecting on a local level.

Culture Shock

Keith Cunningham: When new owners take over a company, skepticism is usually the default setting inside clusters. What were the first messages you delivered to hundreds of stations? These stations didn’t know you or Connoisseur. Furthermore, they weren’t sure what the future looked like.

Keith Dakin: I made the same joke you did at the start of this article: “Yesterday we had 13 stations. Now we have 213. So bear with us.” My message — and certainly my CEO Jeff Warshaw’s message — has been crystal clear. We are a company that is going to do radio in the way we all grew up loving radio. We are going to be in parades and in front of shows at the amphitheater. Additionally, we are going to stop being wallpaper. We are going to connect on a one-to-one level. Finally, we are going to create and make stars.

Scale vs. Identity

Keith Cunningham: One of the biggest criticisms of consolidation is that stations lose their identity. Consequently, they start sounding the same — same imaging, same promotions, often the same voicetracked DJs. How do you scale without flattening brands into generic versions of each other?

Keith Dakin: Is it having a ton of meetings and saying “stop using AI to make your social media graphics”? Because I’ve certainly done that.

Generic, boring radio will be the end of us. It is not Spotify. It is not corporations. It’s not that young people don’t care. Rather, it is doing cookie-cutter, bland radio. Yes, we have national contesting and DJs that do multiple markets. Yes, we utilize super hi-fi. However, I spend every call encouraging these PDs to disrupt, to create, and to make memorable radio. What did you do this week that someone will talk about in their group chat? If the answer is nothing, then we are doing it wrong.

We can all give away the flyaway to Metallica in the Sphere. Yet, how are you — The Fridge in Dayton — going to make it your own? How are you going to make it stand out?

Evolution

Keith Cunningham: You’re in a rare position. You can drive evolution across hundreds of brands at once. When you think about radio’s next chapter, what’s the first area you believe needs to change?

Keith Dakin: Attitudes. If you think radio is ending, if you think today’s the day you’re getting fired, or if you think that no one cares anymore, then you should do something else.

The news is bad. I get it. However, if you are still here and still get to wake up every morning and work at a radio station, let’s make it the best radio station. We’ve hired hundreds of local salespeople around the country since we started. I need my PDs and jocks to preach innovation, success, and excitement. When you talk to Jazzy at KMVQ in the Bay, you want to go out and sell 15 packages immediately. You are energized! Moreover, I need everyone to be like this.

The attitude that the sky is falling will get us nowhere.

Local Talent in a Voicetracked World

Keith Cunningham: Alpha Media was the first company to put an AI DJ on the air. Voicetracking is decades old. And now companies are offering full 24/7 AI-driven programming. How important is live and local talent to Connoisseur’s strategy now? Additionally, with full-station AI already here, how far do you think this goes?

Keith Dakin: Phil Becker did a lot of things at Alpha. But boy, this is the one that keeps coming up. I hope he does something nuts with Cox, so we can stop talking about this! Ha.

There is a big difference, to me, between having someone like Kenzie — based in Saginaw — voicetrack a bunch of our markets and having a robot do it. I’m 100% anti-robot. Perhaps someday this quote will come back to haunt me (hopefully not in a Terminator 2 sort of way). But I can’t imagine that the public wants a fake person on the air.

Now, if you are a morning show and want a parody song or a quick stinger jingle, and you want to use AI, have it. Many shows use actors as callers anyway. If a robot can do that and sound real, I guess I’m fine. But replacing real jocks? No way.

The argument I keep having relates to listener testimonials. Many PDs I speak with say they want to create them in Eleven Labs. “They sound real,” they say. I just don’t think they do. Do you, fake robot, really love the guitar solo in Even Flow? Isn’t it just so much better to have the street team interview real people at one of your events? These people can say, “I love when PLR plays Jaded after Brain Stew when I’m driving on 95 in New Haven.”

The Talent Pipeline

Keith Cunningham: The talent bench is thin. When you need to fill a slot in a small market, where are you looking? And what do you do if the right person doesn’t exist or doesn’t fit the budget?

Keith Dakin: Talented people are everywhere. For example, our morning show co-host in Portland was a reality TV star. Anna — of the Anna and Raven Show — was a stand-up comic, real estate agent, and English teacher. Furthermore, Iris in San Antonio was the receptionist.

We just need to hunt for them. No one is graduating from Syracuse and sending out 82 cassettes to every alternative station in the country like I did. That part is over. So now we, as programmers, need to find them in our towns.

You have influencers, podcasters, and fake internet celebs in every town — big or small — in America. Go find them. Put them on the air. Then you, successful radio professional, teach them how to be great. Find the stars. Teach them how to run the board.

Data & Gut

Keith Cunningham: While there are countless PDs under your watch, you’re responsible for the performance of hundreds of stations. What data matters most to you when building strategy for brands that are struggling? And when does gut override the numbers?

Keith Dakin: It’s revenue. We have to stop worrying day in and day out about the ratings. I have some stations in two-book diary markets. Is that really a roadmap to success? Oh, we were up in Palm Springs in Fall 2025. But it won’t be until six months later until we get another report card. It is no way to determine where you are at.

So, judging our success by revenue is what makes the most sense. Then we can look at things like: Are the DJs stars in their market? Does the morning show have a million endorsements? Is there a buzz on the street? Do our NTR events sell out? Do people interact with our social?

Z93 in Dayton is my favorite example. We flipped that JACK station to Z. Z was a very successful Top 40 that ended many years ago. The excitement of the return of that brand was like nothing I’ve ever experienced. PD Java Joel and I were basically flabbergasted by the response. Now, almost a year later, it still feels great.

Artists and Labels

Keith Cunningham: Aspiring artists have endless platforms — YouTube, Spotify, TikTok, you know all of them — what advantages does radio still bring to labels and artists that those other platforms don’t?

Keith Dakin: I think we all say it. Radio is the megaphone. You can have a massive streaming hit. But your aunt won’t know it until the radio plays it. When KLLL in Lubbock plays your song, everyone in town now knows it. When WALK gets on a record, you know that you have reached the mountaintop. You will hear that song at every wedding for the end of time.

I also believe that we can still break records if we would just do it. Fifteen alternative stations added Phoebe Bridgers when her new song came out. Her new, accessible, alt-friendly song. Why didn’t everyone? Who is bigger than Phoebe Bridgers in the alt space? She opened for Taylor Swift, sold out arenas everywhere, and basically has been a template for a million new pop superstars. We just have to remember that sometimes we can take chances here. (And by the way, playing Phoebe Bridgers is not taking a chance.)

Lessons From Alpha

Keith Cunningham: Acquiring a company comes with surprises — culture, systems, talent, politics, and the stories that come with any acquisition. What did you learn from inheriting Alpha Media? How did this change or help how you lead today?

Keith Dakin: The number one thing I’ve learned is from watching Jeff. He has made it his mission to go to every market — from Fort Dodge, Iowa to Anchorage, Alaska. He has been clear, concise, and direct with what his vision is. Moreover, he has been clear about what he expects from people.

I think you could take any one of our programmers and say, “What is this company about?” They would all give you a similar answer. There is no grey area here. People know what is expected of them. Furthermore, they know they are here to deliver it.

So knowing the mission from the very top makes it very easy for someone like me to help get us there. I’m sure that all the PDs feel the same way: “I need to be here every day and have urgency, be sales-friendly, and a creative mad scientist. I need to impact the community as much as possible. Perfect. Let’s get it.”

Where’s the Weakest Link?

Keith Cunningham: Compared to when you started in the industry, radio has fewer resources, smaller staffs, and less experience inside clusters. What’s the weakest link in radio right now — and what’s the fix that isn’t being fully addressed?

Keith Dakin: It’s simply passion. We just need to get that thrill back.

It starts with market managers. If you have a great market manager that loves the industry and is obsessed with their radio stations, goes to the events, and laughs with your morning shows, then everything else falls in line.

One of our regionals is Kristin Okesson. She is also the direct MM of Long Island and Connecticut. Next week, she will be putting wristbands on listeners at their giant pizza event. Guess what? She’ll be happy to do it.

She has passion. In turn, the sales managers and PDs have it. Then it trickles down to the on-air staff and sales folks. All of a sudden, we are swimming in the same direction. Maybe we aren’t talking about how it was better in 1989.

The Revenue Lever

Keith Cunningham: Programming and sales have never had to work closer together. Given the revenue pressures the industry is facing, what’s the one lever radio needs to pull? How can we grow revenue — not just protect what’s left? Is there one the industry is ignoring?

Keith Dakin: Build big morning shows. Have massive events. These morning show NTR drivers aren’t a fix that is going to save our industry. But will it help us hit August? Maybe. If you have and build stars and believe in them and trust them, the rewards will be never ending. Chaz and AJ in CT never have an event that doesn’t sell out. In four hours, they raised almost 200K in cash and toys for kids. These type of shows make a difference.

If podcasts — PODCASTS! — can sell out theaters, why can’t we?

The Toughest Call

Keith Cunningham: You and the corporate team have had to make some tough decisions. Personnel changes, format flips, station sales. What’s been the toughest call you’ve had to make since Connoisseur acquired Alpha?

Keith Dakin: It’s less of a call but something that has become really interesting to me. People don’t want to move. I’ve had great job openings and talked to some very talented people. But when it comes down to it, they don’t want to leave wherever they live. This is true even if they are out of work. I believe so many radio people have been burned by layoffs over the years. They would rather do a million side hustles than leave Indianapolis or wherever. It has been fascinating trying to hire. At the finish line, I hear: “I just can’t leave where I’m from.”

And believe me, I get it.

The Blank Slate

Keith Cunningham: Last question: blank slate. Say anything you want to any sector of the music industry. What do you want them to hear?

Keith Dakin: Don’t count us out.

Barrett Media produces daily content on the music, news, and sports media industries. Sign up for our newsletters to stay updated and get the latest information right in your inbox.