Meet The Leaders is a special 8-week series created in partnership with Point to Point Marketing. Our final feature is on the Chief Executive Officer of Townsquare Media, Bill Wilson. Follow along with the series and revisit former conversations by checking out the entire category.
Bill Wilson joined Townsquare Media in September 2010 and previously served as Co-Chief Executive Officer and Executive Vice President, and Chief Content and Digital Officer of the Company. Before joining Townsquare, he was President of AOL Media from 2006 to May 2010. During his nine years with AOL, he was responsible for the company’s global content strategy. He also held multiple positions including President, AOL Programming & Studios, and Executive Vice President.
Wilson also served as Senior Vice President for Worldwide Marketing at Bertelsmann Music Group (BMG), which he joined in 1992. His duties involved worldwide marketing including artist, digital and non-traditional marketing across more than 50 countries for the world’s biggest artists.
Bill has been recognized as one of the industry’s brightest and most influential people several times by many publications. He’s even won an Emmy Award in 2006 for the record setting Live 8 program.
In this edition of “Meet The Leaders,” we dive into his day-to-day duties guiding Townsquare Media, why the company prioritizes markets outside the top 50, the company’s plans for expected deregulation on ownership caps, and his focus on partnerships with other broadcasters to expand reach for all parties involved.
Wilson spoke with Barrett Media from his office in New York.
*Editor’s Note: Answers have been edited for clarity and length.*
John Mamola: You began your career at the inception of Townsquare Media. How would you say your role has evolved from the time you started with the company to today?
Bill Wilson: When I began at the company in 2010, I joined as the chief digital officer. My primary role at that time was to determine the strategy on diversifying our revenue streams and our assets so that broadcasts would still be relevant and important to our company but wouldn’t be the only division driving revenue and profits.
That was what I was hired to do back in 2010. Over the years my role adjusted. I became the chief content officer as well, overseeing all of the DJs and content that we create for our mobile apps and websites.
About six or seven years ago the chairman and co-founder of the company, who was the CEO, decided to relinquish the CEO duties. Then I moved into this role. So I guess about six or seven years ago I became CEO of Townsquare.
John Mamola: I’m not telling you anything you don’t already know. Townsquare Media is the third largest owner of radio stations in the country. You have around 340 stations in over 70 markets. From your seat, how do you ensure growth where everybody sees an upward trend across the country with that many stations?
Bill Wilson: As you noted, we have over 300 radio stations. We’re now in 74 local markets. A core founding principle of our strategy was to stay outside of the top 50 markets for two reasons.
One, we felt radio is even that much more important from a connection standpoint to the community. We reach, on average, in our 74 markets, one in two people just by our FM and AM signal, which is pretty incredible. In a top 50 market, the number one market share would probably be 20 to 25 percent.
You can see in smaller markets, particularly in the last 15 years, the newspaper industry has obviously gotten decimated. Plus, in the last six to seven years, cord-cutting has really decimated traditional television broadcast. More people listen to AM/FM radio today than 10 or 20 years ago, which speaks to the power of the medium, particularly in the face of everything from Netflix to Spotify to TikTok competing for people’s attention.
In terms of the revenue trajectory, I bring up that focus on markets outside the top 50 because literally every market of our company can drive positive results. On the flip side, if a market is having a bad year, it can really impact the overall financials for the company.
So it’s quite different than some of the larger public companies who have markets outside the top 50 but whose revenue and profit concentration is likely quite different, where the top 50 markets probably make up the majority of their revenue and profits.
For us, radio has been a traditional cash cow, but the revenue has been declining over the last several years. The growth is coming from digital advertising and marketing solutions from a revenue and profit perspective.
John Mamola: Do you not see that any sort of penetration into the top 50 markets would lead to revenue growth?
Bill Wilson: For the people who are in the top 50 markets and the companies that are there, I’m sure their asset base and strategy works well in the top 50 markets. For us, our growth engine is digital advertising and digital marketing solutions. The competition outside the top 50 markets is so much less than in New York or Chicago.
That’s another reason why we never went into the top 50. Not only because radio is that much more powerful, but also because our strategy for growth in revenue and profits is on the digital side. There’s a lot less competition.
We feel like we’re bringing national scale and sophistication of a full-service digital agency to smaller markets in the U.S. We think that’s highly differentiated. Not that it wouldn’t work in the top 50 markets, but we think being outside the top 50 markets is a real differentiator for us at Townsquare.
John Mamola: The industry has been following the story this year of Connoisseur Media purchasing and selling stations across the country. Regarding Townsquare Media, are you interested in buying or selling any of your radio brands? How satisfied are you with where you’re currently at? Is there any consideration to purchase in the top 50 markets?
Bill Wilson: There’s really no consideration in the top 50. We’ve had multiple opportunities over the past 15 years. Assets like CBS Radio and others have come up with a heavy concentration in the top 50. We stay exclusively outside the top 50.
In terms of potential acquisitions and M&A, a lot is going to transpire. We believe deregulation is going to take place in the middle of next year. We believe the caps in terms of ownership limits will be loosened. So I think there will be a lot of activity, be it swaps or purchases.
For us, the company has been built through acquisitions. We started with only a dozen and a half markets, and now we’re in 74. That’s through, I don’t know, maybe a dozen acquisitions of radio properties. The last one was Cherry Creek about three and a half years ago. That has worked out well for us and the markets we acquired.
We know we have a strategy that works when we acquire a traditional broadcast company that may be doing some digital but isn’t proficient or doesn’t generate the majority of its revenue from digital. That said, we started a media partnership division last year. We’re now white-labeling our full-service digital agency capabilities for others in broadcast. Probably the largest partner we have is Summit, which is a private broadcaster in about nine markets. We’ve signed up over six partners who are all currently in local radio, with some in TV as well.
We see the opportunity to continue to grow our penetration into other markets we don’t own through partners in this media partnership division. Over the next three years, we’ll grow from under ten partners to probably over 25. We may do acquisitions, but it’s interesting because we have two paths.
We can move into new markets through acquisitions, but we can also move into new markets without deploying capital to purchase assets by partnering with others in local media. It could be broadcast television, radio, or outdoor.
It’s going to be a very interesting couple of years for the industry with deregulation, acquisitions, and swaps.
John Mamola: With the expectation that deregulation will happen by mid-next year, are you having conversations internally about strategy on potential targets or potential markets you want to look into if those caps do indeed come off?
Bill Wilson: Yes, 100 percent. We’ve been war-gaming this for about six months now.
We have a map. Who we currently compete with. Which markets we’d be most interested in. Who owns those markets. What the media landscape looks like. Whether there is a local television station and who owns it. How many there are. Is there a local newspaper? Is there a heavy presence of outdoor? We go pretty deep. Not only the strategy but the details.
We’ve also had informal conversations with others in the industry about what they’re thinking. We’ve started the process. Whenever those rules get changed, we’ll be in a position to act accordingly.
John Mamola: Townsquare struck a partnership deal with Audacy in Michigan recently, which led to the creation of the Detroit Sports Network with 97.1 The Ticket. How did that situation with Audacy develop and come to fruition?
Bill Wilson: Kelly Turner, who was named the CEO of Audacy earlier this year, and I go way back. We worked together at AOL Time Warner in the mid-2000s.
When she moved into that role, she and I had dinner with Chris Oliviero and Erik Hellum, who is our COO at Townsquare. We know Chris really well, not only from Audacy but from his CBS days.
We sat down and had a great conversation about the industry, where Audacy was going under Kelly’s leadership, and what our priorities were. It was a natural extension of that conversation to explore opportunities where we could both benefit.
97.1 The Ticket in Detroit is one of the best sports stations, if not the best, in the U.S. We knew Audacy and The Ticket didn’t have a presence in other Michigan markets. There was clearly an appetite for this type of programming. So we proposed extending their brand and coming up with a financial arrangement that worked for both sides.
That’s how it came about. I think we’ll be doing other things with Audacy as well moving forward based on Kelly’s leadership and shared interests.
John Mamola: In addition to the Michigan arrangement, you also have a deal with iHeartMedia in Minnesota. You’re featuring programs on KFAN that you’ve clearly seen value in for regional opportunities.
What are the advantages of this model as opposed to utilizing a national sports network? Is this a model you’d explore in other markets? For example, you mentioned Audacy. They just launched the Wisconsin Sports Radio Network using their Milwaukee brand at 105.7 The Fan as the flagship.
Do you see other opportunities around the country in states or regions that have a singular dominant market that could spread wealth for everyone involved?
Bill Wilson: That’s definitely an obvious one. So yes, I’d say that’s a starting point. Currently we don’t have stations in Wisconsin, but that is a starting point.
We also work with iHeartMedia, as you noted, so there are opportunities there too. We look at all the best programming we generate from our own personnel. Then we supplement that with great brands from great partners like Audacy and iHeart.
John Mamola: Townsquare has been a leader in building brands in the digital content frontier for years. It’s impressive how much the company has invested in building the digital ends of your radio stations.
You’ve often referred to the radio side of the business as the “Trojan horse” to assist in building the digital side. Moving into 2026, could the reverse also be true? Could the digital entities you’ve built lift the radio properties in your markets?
Bill Wilson: It’s a great question. We have digital brands like “Taste of Country,” the number one destination for country music fans in the U.S. in terms of mobile app and website traffic. Also we have similar brands for other genres like “Loudwire,” a hard rock brand.
We partnered with Compass Media and extended those brands from pure digital to radio. We’ve grown that into nighttime and weekend shows branded as Taste of Country Nights and Loudwire Nights. We also have XXL, the number one hip-hop brand in the U.S.
Compass has syndicated them to dozens of markets outside of Townsquare, extending the footprint of our digital properties. I expect more of that moving forward.
We are very active in taking all of our assets and figuring out which platforms will extend our reach and interest consumers. Our ratings on these radio programs that started as digital brands have performed well.
John Mamola: Am I right on this? I saw over half the company’s total revenue is tied to digital this year. Is that correct?
Bill Wilson: Yes. Importantly, not only the revenue. It’s about 55 percent of our revenue, but also about 55 percent of our profits being driven by our two digital divisions. Many companies are working hard to diversify their revenue base, which I applaud.
One thing that differentiates Townsquare is that our profit margin on our digital properties and divisions is equal to, if not greater than, our broadcast business. There was a term in the last 10 to 15 years where people said you were trading broadcast dollars for digital pennies or dimes.
For us that couldn’t be further from the truth because of the profit margin.
Going back to your question, yes, the majority of our revenue and profits are driven by our digital divisions. That will continue. Over the next three to five years, I think we’ll be approaching 80 percent of our revenue and profits coming from digital, with digital growth remaining strong.
John Mamola: I want to ask you about evaluating the performance of a Townsquare employee. How do you determine if your market managers, programmers, and everyone at your local radio stations have had a successful year with the revenue trend leaning more digital than traditional?
Bill Wilson: We’re quite blessed to have a tremendous executive team. We have regional vice presidents managing local markets, and each market has a dedicated market president. We’ve had great tenure and loyalty throughout the ranks, which has helped us transform from a traditional broadcast company to a digital-first local media company.
In terms of measuring success, one important thing as a leader is making sure everybody knows their responsibilities and how they can measure their own success. It’s one thing if I can measure it, but I want each team member to know if they’re doing a great job.
There’s data they can look at without talking to their manager. They know if they’re achieving their goals. We give them goals at the beginning of the year and adjust if needed.
For local DJs, in the past it was almost entirely ratings driven. But many markets we’re in aren’t even rated anymore because Nielsen has exited several markets.
We still look at research indicators: inbound calls, brand connectivity, social media engagement.
If you’re a local DJ, your role changed in 2010. You not only host a local show that informs or entertains, but you also write content for our websites and mobile apps.
They receive real-time feedback on what they’re writing and how it’s connecting with the audience. They use that feedback to understand what resonates. If they are rated, they get a book two to four times a year, but with real-time data they know instantly what connects.
That’s crucial for a company with so many markets and over 2,000 team members. Everyone must know what success looks like for the company and for their own role.
If you’re a salesperson, it’s not just how much revenue you generate but how much new business you generate. We’re agnostic about what people sell. We don’t push broadcast over digital or vice versa. It’s about selling what’s best for the client to ensure repeat business.
We focus on clarity—knowing your role, your responsibilities, and what success looks like.
John Mamola: In markets where you have competition from the top two groups, what do you consider the point of differentiation? What does a Townsquare product or personality have that’s a must-have for a client?
Bill Wilson: From a pure broadcast perspective, I think we’ve done a tremendous job protecting the local nature of our content. Syndicated and national content can work, but our focus on local is what differentiates Townsquare.
From a client perspective, we offer a full-service digital agency. We sell solutions that work on our websites and mobile apps, and we have a full programmatic division. That’s the division we white-label for others.
Five years ago, we couldn’t sell a television commercial. Now it’s the fastest-growing revenue in the company.
Competitively, even the larger players in top 50 markets don’t offer the breadth of products, insights, or first-party data that we do. Our reporting not only shows how media spend works but how marketing messages perform. Clients can use that for things like in-store merchandising.
We’re highly differentiated in breadth, sophistication, and data. We invest heavily in data and provide insights based on it. We know it’s differentiated because we’ve seen other reporting from broadcast, TV, and outdoor companies.
Having first-party data, a data warehouse, and audience insights is highly valuable for clients.
John Mamola: Back in June, you said you were frustrated with the company’s stock performance because it was being classified in a neighborhood that you said doesn’t live anymore, which you said was the radio industry. Where is your confidence level moving into 2026 that shareholders will take greater notice?
Bill Wilson: I think it’s important because sometimes our vernacular gets misinterpreted. Particularly on earnings calls, I try to highlight this.
We love broadcast radio, and would not have the success we have in digital without the power, connection, and companionship of local radio. We don’t view radio as the growth engine, but as a core part of our DNA and offering. It’s highly differentiated and high impact for both audiences and clients.
I want to be clear about that. Sometimes people say Townsquare doesn’t love radio and is focused on digital. The reality is we love radio and we’re really into digital. Those statements are not in conflict.
In terms of the stock price, we have not performed at the level we wanted this year. Our broadcast business is down roughly eight percent year to date, and the industry is down low double digits from a spot perspective. It’s a challenging environment. There are great broadcast companies with different strategies and assets.
Over time, something important to note is that many companies in the broadcast space are highly leveraged with much higher debt loads relative to profit. Our perspective is to stay focused and execute. Over time, shareholders will be rewarded with a higher share price.
In the meantime, we have a high-paying dividend. The yield is now in the double digits. Investors are being rewarded with a hefty dividend while they hold the stock and look toward future appreciation.
As long as we consistently grow profits and revenue minus political spending each year, the stock price will take care of itself. That’s our focus: consistent organic revenue and profit growth over the next five years.
John Mamola: Is there anything that can be done to turn the revenue story around for the broadcast end of the business?
Bill Wilson: I think there’s an opportunity for stabilization of pure broadcast spot. Once stabilized, I think there is potential for growth. A key part of that is utilizing talent.
Doing endorsements has a significant impact for clients. About five years ago, broadcast television was the number-one-reached medium at 96 percent of America. Now radio is number one with over 90 percent penetration. More people are listening today than 30 years ago.
The important part is doing something that stands out. Endorsements, live reads, and other elements. We’ve seen positive results in client testimonials.
I definitely see the opportunity over time to reverse the trends of the last 10 years and stabilize and potentially grow.
John Mamola: What excites you about your job and lights the fire within you for a big 2026 for Townsquare Media?
Bill Wilson: I couldn’t be prouder of the team. We have an amazing team across the company. I feel blessed, privileged, and honored to represent them.
What drives me today is the same thing that brought me to the company 15 years ago: making sure these communities are served with great information, news, and content. And making sure clients and businesses can partner with us so we can help them achieve their goals through our broadcast and digital platforms.
What sparks me is that I joined the company in 2010 because I loved radio. As a kid, I’d listen to the radio all the time. When other people were watching TV at night, I’d have my headphones on listening to great radio. I joined because I wanted to make sure radio always has a place and is important in the U.S. and in these markets.
That still drives me today.
I want to make sure that if you’re a DJ, you’re relevant 30 years from now. Relevance looks different today than 30 years ago, but you’re even more relevant now. Thirty years ago, your brand was primarily on air and at remotes. Now your brand is across all social platforms, and the reach is significant.
That’s what sparks me. I want to ensure the broadcast industry is thriving 30 years from now. The only way to do that is to look at your assets and ask how we can continue to drive profits and revenue, even if it’s not coming specifically from broadcast.
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.
John Mamola is Barrett Media’s sports editor and daily sports columnist. He brings over two decades of experience (Chicago, Tampa/St Petersburg) in the broadcast industry with expertise in brand management, sales, promotions, producing, imaging, hosting, talent coaching, talent development, web development, social media strategy and design, video production, creative writing, partnership building, communication/networking with a long track record of growth and success. He is a five-time recognized top 20 program director in a major market via Barrett Medi’s Top 20 series and has been honored internally multiple times as station/brand of the year (Tampa, FL) and employee of the month (Tampa, FL) by iHeartMedia. Connect with John by email at John@BarrettMedia.com.
