Meet The Leaders is a special 8-week series created in partnership with Point to Point Marketing. Today’s feature is on the Senior Vice President of Programming with Connoisseur Media, Keith Dakin. Follow along with the series and revisit former conversations by checking out the entire category.
Keith Dakin has built a distinguished career in radio spanning more than two decades, developing a reputation for programming excellence, creative thinking and an ability to grow brands across multiple formats. After studying at Syracuse University’s S.I. Newhouse School of Public Communications, he launched a career that took him from Cox Media’s Richmond, Virginia, operations to programming Boston’s influential WFNX. Today, he serves as senior vice president of programming for Connoisseur Media.
His accomplishments include 11 Marconi Award nominations and a win, as well as developing The Anna and Raven Show into a nationally distributed program heard on more than 100 stations. He has also created successful revenue-generating events, ranging from community pizza festivals to large-scale concerts, while delivering consistent ratings results.
In this edition of “Meet The Leaders,” we dive into the challenges of taking on so many stations through acquisition, how to scout talent today, the characteristics of leaders. Also, we dive into his working relationship with CEO/Founder of Connoisseur Media, Jeff Warshaw and where he sees AI playing any significant role in radio for the future.
Dakin spoke with Barrett Media from his offices in Connecticut.
Editor’s Note: Answers have been edited for clarity and length.
John Mamola: You’ve been with Connoisseur Media for over a decade and have seen the company grow from the inside out. With the company’s acquisition of Alpha Media, you saw that growth rapidly increase from 13 stations to over 200. It wasn’t a slow climb by any means.
How did the experience prior to the acquisition prepare you for the task of taking on that amount of growth so quickly?
Keith Dakin: Over my time period, sort of in the role of head of programming for Connoisseur, even the original version, we had big markets like Long Island. Then over the years some of them came and went. We had smaller markets that I did stuff with, like Frederick, Maryland, and some stations in Pennsylvania.
No one’s ready to go from 13 stations to 200 stations. But I’ve been used to dealing with both big and small markets and the challenges of both. As well as big talent, as well as people doing 50 jobs in the smaller markets.
So, I was sort of ready for it. It was just such a massive scale.
John Mamola: What was the biggest challenge for you, but also what was the biggest benefit from working through that process?
Keith Dakin: It was a hundred percent getting to understand and know the brands.
It’s beyond just radio station name and frequency. Understanding how much The Big DM means to Columbia. 101.9 KINK in Portland, which I sort of knew about because it’s such a famous radio station. Understanding their legacy and history.
Then it’s almost like if you move to a new city and start to follow their baseball team. All these baseball teams have so much lore from the past. You can’t move to Boston and be a Red Sox fan but not understand [Carlton] Fisk’s home run and Bill Buckner’s ball through his legs.
This is what it was like with these radio stations. What are they? What were they, and what did they become? That summer of 2025. It was just educating myself on these stations and what they’re about.
John Mamola: With all these conversations that you’ve had with the local leadership in all these markets, what are the characteristics that you’re looking for when you’re building those working relationships with so many people in those markets?
Keith Dakin: The number one thing — and I’ve said it sort of in other interviews — is urgency. When I’m looking to hire, not for on-air so much, but when we’re looking to hire programmers or even promotions people, I just need them to be doers. I need them to react. Like, text back quickly. Sounds stupid, but that sort of thing.
When we need to do something, I don’t want to talk about it for five weeks. I want to start doing it. If we get the green light to hire, let’s get the ad out, start interviewing, and bring people in. Let’s not sit around. Sometimes we just got to do things. If you look at the people we’ve hired since we started, they all have that quality. They’re doers, go-getters with a passion for radio. They respond.
If any of my people aren’t responding, then we’ve done something wrong. I want people to get it heard.
John Mamola: What’s the day-to-day like now for you? Because I imagine all these added stations and all this added oversight, I imagine the schedule has to have changed just a little bit right now.
Keith Dakin: On May 4 of 2024, I was doing logs, sometimes on the air. Also writing imaging for Connecticut radio stations and all that.
Now, it’s like a thousand phone calls. Basically I talk to my format coordinators every week. I talk to the regionals every week. Basically one-on-ones. I talk to a lot of the operation managers and market managers every week, on top of our key air talent. I do a lot with The Anna & Raven Show, who we have syndicated on a hundred radio stations now.
Then, I’m actively involved in conversations with Jeff [Warshaw – CEO, Founder Connoisseur Media]. Jeff lives here in Connecticut, where I live. I’m talking to him a couple times a day about everything from business to his favorite songs to various markets. He’s traveling as much as I am, so we compare notes about the markets and all that.
John Mamola: What’s your working relationship like with Jeff [Warshaw]? How has it evolved over your time working with Connoisseur Media?
Keith Dakin: It’s wonderful. My relationship with him is like no relationship I’ve had in radio. When you think of people that own radio companies and CEOs, you don’t think they’re going to call me and tell me that bit was great. Or they’re going to be in a market and wonder why this song is playing.
His passion for what we’re doing and what comes through the speakers, on my end, is unbelievable. On top of it, like, he knows all the players. He has been to every one of these markets. He’s treating these stations like he always treated Connecticut, which was a station in his backyard. Now all of America is his backyard. He has made personal relationships with a lot of these jocks, and certainly the market managers.
It is wild. It’s very impressive.
John Mamola: I love Jeff’s [Warshaw] passion for investing in people. Connoisseur Media is a company that continues to build stations with impact in local communities by investing in local talent.
Yet, the greater majority of the industry continues to cut costs and people. From your chair, what is it about the formula that Connoisseur Media provides that drives that mantra of investing in local talent, where others don’t?
Keith Dakin: This is all a very difficult business.
We are in a business that, as much as we try, is not growing the way we want it to. I desperately am hoping for radio [to] become [vinyl] records. That people want to be into it. Young people think it’s cool, and we become the next big thing.
So, we’ve done everything we can to establish our footprint in these local markets. Hire OMs and salespeople and make sure we have morning shows. Now we just got to hope it works. It’s been the big experiment to go back to doing radio the way it was.
With a business that, to be honest, seems to be shrinking. Let’s hope it lasts. That’s what I’m hoping for. We have a lot of opportunities out there with the digital side of things. We own a company called Next Rodeo that does media buying, and it almost works as a de facto ad agency.
If we have a larger web and a bunch of different opportunities to bring in revenue, I think that can help us do what we want. But, you know, everybody knows. It’s extremely tough.
John Mamola: When you go into these individual markets and you talk to talent and leadership, do they feel and believe in that manta of the company investing in local people. Does it resonate in every single market that you go into?
Keith Dakin: It does. The Alpha stations had a lot of challenges. We’ve tried to turn the ship around here, and we’ve tried to fill some holes and do a bunch of things to make these markets feel whole, or at least a little bit better.
There’s always going to be a situation where we use technology. For instance, we use Super Hi-Fi to help us with some of the costs. But, if you walked into a market, that you would say they’ve got a real morning show. They’re doing things. They’re on the streets, have handouts, and stuff like that.
I would think the markets, if you talk to them one-on-one, feel better than they did two years ago.
John Mamola: You brought up digital. Podcasting consumption and usage continues to surge where the on demand is overtaking the live usage. Other broadcast companies have been investing in building their own podcast networks with their digital strategy. How satisfied are you with where Connoisseur Media is so far when it comes to that wing of the business?
Keith Dakin: I think we could certainly do more. All our big shows podcast. We have some specialized podcasts as well. The future for us is getting our key talent to do podcasts of things that they’re interested in, and then we can promote it over the air.
We’ve been really spending the last year trying to get all of our kind of ducks in a row. A podcasting strategy and building out podcasts that are less greatest hits of any of our talk shows, it’s something that we need to focus on moving into the next year.
I will say that the morning show stuff, basically all of our big ones do it. It all does very, very well. It’s been very successful, especially when you look at markets like San Francisco.
John Mamola: In addition, more people are consuming podcasts and live programming on video than ever before. The streaming platforms hold live content at a high value. I would imagine that’s also part of the digital strategy that you’re continuing to develop.
Keith Dakin: Yeah, and we’re doing it. A lot of our big morning shows are already doing that. I think it’s awesome. This is such an old reference but remember when Howard Stern was on E!? I was so into that, and now every one of these shows could do it.
John Mamola: Big part of any programmer’s role is scouting talent. There are so many more avenues to look for people and bring into your brand. Where do you look for that next generation of talent?
Keith Dakin: I joke that I sent out 85 demo tapes the day I graduated college to the 85 alternative stations in the country at the time.
Nobody is doing that anymore. A lot of what we’re looking for when we put a job out, I’ll hunt. Social media, YouTube, podcasts. That’s where we’re gonna find the people, and then we teach them radio.
The smartest thing is, as far as on-air goes, you find somebody that is interesting, compelling, could tell a good story, is a nut. We could teach him how to run the board. They don’t need to go to Syracuse and know how to do these things anymore. We just need big personalities that we can train to do things.
That’s where we’re kind of finding everyone in that space. Yes, there are certainly great DJs that have been out of work that are from radio. I get those resumes, too. But, it’s great to have a balance.
Where we’re finding people now, it is definitely not showing up at our door. It’s like the joke about sales. In the old days, the fax machine would just come in with orders. Now we have to hunt a little more. We got to work our ass off a little more to find people that are great.
John Mamola: I read an interview you did with our own Keith Cunningham where you said it was hard to get talent to move away from the markets where they already live. There’s lots of factors that go into that, and they’re not all the same.
What’s the balance for Connoisseur media when it comes to talent living in the market they broadcast from? Is it a hard line on desiring all talent on our stations to live in the markets they broadcast?
Keith Dakin: No. For instance, we have a woman named Kenzie, and she lives in Saginaw, Michigan. She voice-tracks in a number of our different markets because she’s awesome.
But the difference between Kenzie and others is that she researches the market, talks to the PD, knows what’s going on, and passionate about what’s happening in these markets. I do think if you are a morning show, you should probably live in the market. Unless we’re doing a syndicated morning show thing. But, I just don’t know how our morning show in Portland sounds like Portland without sort of being there.
But, for these other dayparts, if you have the right person that commits, cares, and uses all the tools available to them to sound local, I think it’s okay. What I want in a perfect world? Does everybody live in the market, and everybody goes to every parade? Yes.
I know that’s just not a reality. You just got to find the right talent that will commit to sounding as local as possible.
John Mamola: Big part of the new brands that Connoisseur Media acquired. There’s a lot of AM radio stations that came along with that.
Congress continues to work on the AM Radio for Every Vehicle Act. I know Connoisseur Media has been a big supporter of the legislation. However, what’s the plan with more investment in the viability and brand awareness of those AM bands from a company perspective?
Keith Dakin: Definitely. One of our biggest stations, KTSA in San Antonio, is on AM. They are the news source for San Antonio. We’ve got a local morning show in the Texas Broadcasters Hall of Fame. They break the news. These AM stations, should be everything. They should be where you turn if there’s a disaster.
But they should also be where you turn for the local election. Right here in Connecticut, our AM station, WICC — Melissa, who does the morning there, has had all the candidates on this week. The AM stations and shows, besides the syndicated ones, the local ones should really have a connection to everybody that matters in their community.
If there is an emergency, they know the mayor, the fire chief. That’s what these guys have to do. Not only are they doing emergency coverage, with no local newspapers anymore, they are really the connection to the city. They’re not just a Patch website written by AI.
John Mamola: Speaking of AI, it’s a big-ticket item right now for any company, brand, and talent. Alpha Media was the first company to launch an AI talent at one point. Granted, that’s gone now.
But we’ve seen a lot of radio brands offer a human promise to its listeners while AI music continues to surge in popularity, especially with the younger demos. How do you balance the promise of non-AI content with a growing popularity and genre of AI music?
Keith Dakin: I’m fine with people using it [AI] for show prep. Putting some things together. It’s been a great tool to come up with morning show content. It is a great tool to aggregate local content so they know what they’re talking about. Side note: they should probably research it make sure it’s accurate.
It’s real helpful in that regard. But, I’m really on the fence about using it for anything else. I hate using it for voices, even for fake listener testimonials. I would much rather have real people do it. Around the country you hear, “I love Pearl Jam,” but it’s the robot.
As far as music goes, that’s really a case-to-case basis. Personally, I’m against it, but I’m a hundred. So, maybe I’m wrong. At this point, I think we’ll take it one step at a time and see what comes up then go from there. For some of these editing tools and to make cool graphics, okay, sure.
Would I much rather have a real graphic designer doing real graphics than that AI slop-looking stuff? Of course.
John Mamola: Could you see a day where AI music has its own format on terrestrial radio, where humans are in between songs?
Keith Dakin: Music in general, with the Spotify, Apple Music era, and then TikTok only playing 30 seconds of songs. I have a 19-year-old and a 15-year-old, and it changed the way they interpret music, except they have a nut father that yells about things all the time.
These are fake songs. We should listen to Rage Against the Machine. What are we doing?
I guess never say never. If all of a sudden these AI songs become the biggest thing in the world, you don’t want to miss the boat. You want to be part of the whole thing, right? But geez, U2 is my favorite band because of their lyrics and because of how much passion they have. These robots, oh, I don’t know. I don’t love anything [about it].
John Mamola: You’ve been programming for a while. There’s debate about Nielsen and ratings, and if they’re still as relevant, or relevant at all, nowadays. From your seat, are they just as relevant today as they were maybe a year ago, five years ago, ten years ago?
Keith Dakin: I think ratings have their place. It’s a good barometer of where you’re at. Usually when you see the number one station in town, you say to yourself, “Oh, yeah, that’s right. That feels like number one.”
There’s still a lot of flaws. I’m interested to see what the DTS folks come up with. I’d love to be able to look at my streaming stats that are real and not estimates. But, this is what we’ve all grown up with. Until somebody comes up with a better mousetrap, I think we’re kind of in it.
I would love to see other options. I think we all would. Jeff’s [Warshaw] been an active voice with the Nielsen folks. He’s on their board, and I think he’s tried to push for more change. The stuff they’ve done in a lot of those markets where it’s been continuous diary measurement, I thought was a step in the right direction.
I would love to see a place where people aren’t writing in paper diaries anymore in some of these smaller markets. A lot of times it’s very frustrating. I have a lot of markets that are two book diary markets. That’s tough to live with. It’s kind of the devil we know, but I would love to see some improvement. Either by them or some competitors or whatever.
John Mamola: Now, looking ahead to 2027, top challenge and top item that you’re most excited about with Connoisseur Media?
Keith Dakin: Top challenge is obviously going to be driving revenue. That’s the number one thing. We talked a little bit about ratings, but really the thing that we should all be judged on is, are we driving revenue? Is there cash flow?
Are these radio stations making money? That’s the number one focus for me in 2027. How can I, and then my programming team, help drive revenue to these radio stations? What can we do better? The number one item I’m looking forward to personally is working with these talent and watching them grow.
Anna & Raven was sort of my project. In 2014, that show started. Kevin Begley and I started it here in Connecticut. Watching them grow to a hundred stations now, making them better and more awesome. Plus, having their ratings go up and driving revenue — that’s the thing I’m most excited to see.
Building more shows and watching them become successful across the entire Connoisseur Media landscape.
To learn more about Point-To-Point Marketing’s Podcast and Broadcast Audience Development Marketing strategies, contact Tim Bronsil at tim@ptpmarketing.com or 513-702-5072.
