Meet The Leaders is a special 8-week series created in partnership with Point to Point Marketing. Our second feature is on the Chief Business Officer and Market President for Audacy New York City, Chris Oliviero. Follow along with the series and revisit former conversations by checking out the entire category.

Chris Oliviero has built a career as one of the sharpest executives in the radio industry. Following leaving the business in 2018 after serving in several key roles with CBS Radio and Audacy (formerly Entercom) based in New York City, Oliviero returned to his home during the COVID-19 pandemic as the brand’s market president. Since rejoining Audacy, he has been elevated to the position of Chief Business Officer. His role includes serving as market president over the company’s New York City cluster.  

In this edition of ‘Meet The Leaders,’ we explore how Oliviero juggles both roles, Audacy’s new distribution partnership with iHeartMedia, Ryan Hurley’s tenure as program director of WFAN, what continues to motivate him, and how he views the health and future of the radio industry. 

Chris Oliviero spoke with Barrett Media from the Audacy offices in New York City, NY.

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

John Mamola: In March, you were elevated to the role of Chief Business Officer with Audacy. What does that entail, and how does it affect your typical day-to-day as market manager with Audacy in New York?

Chris Oliviero: I always joke with people about the CBO title; my middle name is not Brian or Brandon. It is an interesting new job and didn’t exist previously. As you mentioned, it’s now my second job while still remaining the New York market president.

Overall, from just an operational standpoint, my role as CBO oversees both our revenue and our content operations. You might notice I didn’t say our broadcast content or our digital content, because those distinctions are gone. We are one organization, one content org and one revenue org, so overseeing both that.

Spiritually, part of the job is strategic to have one eye on today, but also one eye on tomorrow. To make sure that Audacy is positioned to be a dominant, relevant player in the media space as it moves forward. That comes down to making sure that Audacy, in any incarnation moving forward, is a must-have for both audiences, and then obviously a must-have for marketing partners.

That’s kind of how I look at the CBO role, in addition to that New York market president job.

John Mamola: Is there anybody within the entire industry you look to as an example of a skill set or trait that you steal and apply to your day-to-day with the CBO role?

Chris Oliviero: Regardless of the position I had from the very beginning of my career, all the way through being the head of programming at CBS [Radio] to being the market president to now being CBO, I’ve always had people that I’ve admired. Either I directly worked with them or competed against, and tried to take some of their best attributes and make them my own.

A lot of them were not even necessarily based on business, but how they handled themselves. How they carried themselves, treated people, and helped build culture.

I look back at my career; there are too many to name. Trust me, I’m a thief. I steal from talented people around me.

MAJOR Radio Industry News: @Audacy has announced David Field is stepping down as President and CEO and as a member of the Board of Directors. The Company’s Board has appointed Kelli Turner, a current Audacy Board member, as interim President and CEO, effective immediately. pic.twitter.com/GjfYjkD7Ie

— Barrett Media (@Barrett_Media) January 29, 2025

John Mamola: Audacy senior leadership within the company has shuffled a bit this year. With David Field stepping down and Kelli Turner taking over as the new president and CEO. How would you say that transition has gone so far?

Chris Oliviero: It’s been really smooth. All that credit goes to the employees of the company, not just centrally, but locally in the 45 markets that we operate.

There was a significant amount of change in the spring, a significant number of departures of longtime colleagues at the senior level. When that quantity of change usually happens, human nature is people get nervous. They start to get siloed, and they lose focus. That did not happen this year.

I’d like to say that’s a result of me or Kelli [Turner]. Honestly, it’s a result of the everyday employees who picked themselves up and said change is inevitable in the business, got to move forward, and stay focused on what I own.

That doesn’t mean they didn’t have a relationship with the people that left, but they were able to separate that. There was a job to do, and we moved ahead. So, kudos to them.

John Mamola: You’re currently serving both in local management and on a national scale. For you, what’s the difference in approach between the two? Can you separate the two, and are there differences or similarities in your approach with both?

Chris Oliviero: This has always been something that I’ve been able to point to throughout my career when I’ve had either a corporate or central job versus a local job. The biggest difference is in the local job, you’re able to see your impact, good or bad, quicker. You’re on the ground and face-to-face with your direct reports. You get dirtier in a local job, and I say that in a good way.

Sometimes in a central job, you’re one layer removed. It’s a lot of trying to make sure that people hear the strategy and then hope that the execution takes place.

In the local market, you feel it and you see it on an everyday basis. That’s kind of why I think I benefit from doing both right now. I can see what goes on in the local market, like New York. I can then extrapolate the same feeling that my colleague might have in the local market in Houston or San Francisco, then bring that point of view to the central corporate table.

That’s a benefit. Physically and health-wise, how long can I do both? We’ll see, but I’m enjoying doing both.

John Mamola: One of the more interesting announcements Audacy made this year was in June when you announced the content distribution partnership with iHeartMedia.

Give us a peek behind the curtain. Explain the thought process behind that announcement when you’re approaching a content agreement with a direct competitor.

Chris Oliviero: I’m glad you recognize that because I think that deal early on set the tone and sent the message of what we want the new Audacy to be.

We’re going to be aggressive and be opportunistic. We’re going to throw the old hangups out the door in terms of, ‘oh, this is competition, we can’t do a deal with that person.’

Why can’t we? If it’s good for Audacy, so what if it’s also good for iHeart? Is that so bad if it’s beneficial for both? I view iHeart as colleagues; they’re friends. Of course, we compete, but we compete with a lot more companies outside of radio than just iHeart.

This was our way to say to people, we’re open for business. We’re going to be aggressive, and we’re going to be smart. That deal sends that message, and I think that deal has also been a win for us and for iHeart.

To me, that’s not a bad thing.

John Mamola: How does that announcement shift focus from continuing to build up the Audacy app, if any?

Chris Oliviero: The Audacy app is always going to be our primary destination, our home. When you look at how consumers experience content and how they choose to spend their time during the day, it’s kind of egotistical and selfish on our part to think that we can keep them just to ourselves, that they don’t shop or travel in other places.

If we know that they’re going to be spending time potentially with iHeart or potentially with TuneIn, why not partake in that? That doesn’t devalue our primary platform; this is all additive.

The more data we get back on people’s habits—how they use platforms, both video and audio—it proves that point. Try to be everywhere, as long as the business terms make sense. These business terms make sense.

John Mamola: Audacy hired Ryan Hurley last year as the new programmer for WFAN. How have you seen his role impact the current state of what WFAN is while building for the future?

Chris Oliviero: Ryan also has two jobs. That’s becoming a theme; everybody in radio in 2025 has multiple jobs. He also oversees the Infinity Sports Network, but obviously WFAN is the mothership. It’s the number one sports station in the country and gets a ton of attention.

Ryan had a very challenging job to try to come in and replace Spike Eskin. Even though Spike was here for a very short amount of time, he made a major impact. Spike is now crushing it in afternoon drive on the air. He turned in his management credentials and went back on the air at 94WIP.

Those were big shoes to fill, and Ryan has done a really good job.

One of the things that Ryan is challenged with is what all programmers and brand managers need to be challenged with: How do you make sure that this iconic brand is relevant moving forward on all platforms?

You’re seeing WFAN daily increase its social content and short-form video. We also have a dedicated digital manager in Tom Izzo, who spends an enormous amount of time doing that.

When you experience WFAN now, it’s not just AM, it’s not just FM—it’s truly multi-platform. That’s just going to ramp up more. That’s where Ryan has to have his focus. He’s got to broaden that view, and that’s what he’s doing.

John Mamola: Audacy also announced this summer a partnership between WFAN and Jomboy Media. With the shifts in television with licensing content agreements with creators now bleeding over into radio, as somebody that’s leading a company at your level, how do you grow your own talent pool in the traditional sense and digital realm, balancing that with potential licensing deals which take away opportunity from internal staff at radio brands?

Chris Oliviero: In a perfect world, you would love to incubate and cultivate from the very beginning all of your talent. You would love to have an entire 25-man roster where you wish that all 25 had come up through the farm system from rookie ball all the way through.

That’s unrealistic, but if you can have a significant portion of your talent base come through that system, then be strategic in how you make these partnerships and sign free agents. That’s a more holistic approach.

The Jomboy Media relationship is similar to how we judge the prism of the iHeart deal.

In theory, could someone say we compete with Jomboy Media? They’re Yankee-focused, sports, audio, podcasting compared to what WFAN does. Yes, on paper. We viewed it differently.

We have something to offer them. They have something to offer us. Maybe we’re reaching different audiences right now, so maybe there’s an opportunity for both of us to introduce our brand and their brand to different audiences. We share a relationship with the New York Yankees, so it was an opportunity for us to increase our Yankees coverage.

It’s only been about two months, but the early response is it’s doing exactly what we hoped—which is that there are people who consume Jomboy Media that might not have consumed WFAN. Now we’re open to that, and vice versa.

John Mamola: I recently had conversations with both Boomer Esiason and Craig Carton. I asked Craig [Carton] about a potential return to WFAN if he would answer the call. He said absolutely 100 percent.

I asked Boomer [Esiason] about it as well. He said that he’s 100 percent behind a potential return of Carton to WFAN.

With the way the WFAN lineup is arranged currently, there’s not really a gap to insert a talent like a Carton. I’m assuming from your end of the spectrum, the door is open if there is a possibility, if it’s something that Carton may be interested in doing.

Chris Oliviero: Absolutely. Craig worked here two different times. When he left to go to FOX Sports, he left completely with our blessing. There was no bad blood. He didn’t leave us; we supported it. We understood what that opportunity presented for him and his family.

I do have his phone number, so I do know where to find him.

You are right. WFAN is in a healthy place, but if the opportunity presented itself—again, going back to that sports analogy—if there’s a marquee free agent on the market, you always have to consider that. We view ourselves as the New York Yankees of radio.

If there’s a marquee free agent available, of course we’re going to look at it. The DNA of WFAN is big personalities.

John Mamola: With the understanding Ryan [Hurley] oversees the Infinity Sports Network, for clarification, the broadcasting agreement with Rich Eisen and his program—does that run up at the end of the current year?

Chris Oliviero: The agreement with Rich Eisen is through Westwood One, who is our partner on Infinity Sports Radio. They would be able to officially give you that date, but I believe you’re correct.

John Mamola: Let’s just say that that is the date, since Rich Eisen moved his programming to ESPN Radio in September. As far as finding a replacement for the daypart on the Infinity Sports Network, is that a decision that falls with you, Ryan Hurley, a collaboration of the two of you, and does it include Westwood One?

Chris Oliviero: It’s a complete partnership with Westwood One. Bruce Gilbert, who runs sports for Westwood One, obviously Ryan [Hurley], myself, and Jeff Sottolano, who is head of programming for Audacy. It’s a true partnership with Westwood One. We launched the network in 2012 as CBS Sports Radio. It’s been a long, productive partnership, so we’ll do it together.

John Mamola: We’re now in mid-October. Is that process currently underway?

Chris Oliviero: Yes. I can’t share anything. It is underway because on January 1 there will be programming 24 hours a day, seven days a week on Infinity Sports Network.

John Mamola: In your role as CBO and market president, which metrics matter the most to you?

Chris Oliviero: There are several. Revenue is probably the most important because revenue is what you pay your bills with. This is a business. You don’t pay your bills on ratings.

Sometimes you could have the highest ratings in a market, but if you don’t have a product that clients are interested in supporting with their ad dollars, what good does that do you at the end of the day?

Of course, we love to have big ratings, but revenue is what pays the bills. Revenue is the ultimate metric, but underneath that, ratings are important. Social engagement is important. Can a talent contribute on multiple platforms—meaning can they do audio and video? Are they good at experiential live events in public?

All of those things come together, but at the end of the day, it’s a revenue-driven business.

John Mamola: You’ve been in this industry a long time. This time of year, a lot of people on the ground floor of radio are looking over their shoulder. iHeartMedia just went through a reduction in force last week.

From your perspective, what keeps you motivated and encouraged about the future of the industry, where it seems so bleak for so many people but seems brighter for people in your position and higher?

This will be a big story today. @Audacy is undergoing layoffs. As more information becomes available we will update the piece.

If you're among the affected, please DM or email John@BarrettMedia.com and Jason@BarrettMedia.com.https://t.co/TfLY9cbV51 pic.twitter.com/WqbEBPLeJu

— Barrett Media (@Barrett_Media) March 6, 2025

Chris Oliviero: I’m definitely excited about our future. If I wasn’t, I wouldn’t have come back. I left briefly in 2019 and then ultimately came back in 2020.

Part of the reason to come back was I actually believe in a viable long-term future for the business itself. That said, I don’t have earmuffs on where I’m naive to what’s going on in the larger marketplace.

I know our employees recognize that, but we’ve got to focus on the positives that we have.

Right off the top of my mind, the positives that get me excited—the caliber of the content that we create is something that excites me. The brands that we have, especially with clear dominance in sports and news.

You’re going to hear the CBO in me: the size of our sales force. Audacy has hundreds of salespeople coast to coast who are smart and savvy, who solve problems for brands and clients.

What I would say to people is the industry, in some shape or form, has been around since the early 1920s. Think about how much change and innovation has happened over the last hundred years. We’re in a period again of change and innovation. I am sure in the previous changes in the 1950s and the 1960s, or even in the 2000s when streaming really came through, there was similar uneasiness—but people identified an opportunity and evolved to move forward. As we look forward, we should look back and learn from that. The industry has been resilient for over a hundred years. There’s a reason for that.

John Mamola: Over my career in radio, I chose to move away from the on-air path and elevate into the management side of the radio industry. I wanted to become a program director, a potential senior vice president of programming. There’s not many that share that same kind of passion for that type of path in the industry today.

What would you say to people to encourage them to continue on that path, or begin to investigate that type of path as something that they can advance their career into?

Chris Oliviero: People should be open to change and open to learning new skills. It doesn’t matter how long you’ve been in this business or the age on your birth certificate—you can always still learn new skills and new traits.

Most people aren’t open to that. Most people shut down at a certain point and say, I know what I know. Those people are going to have an issue moving forward, but if you’re open to learning and to reinventing yourself, I think there are plenty of opportunities.

You must make yourself indispensable and make yourself someone that adds value to a company.

Also, to your metrics point, make sure it’s in a way that can be measured. If it’s ratings or revenue, make that pitch. Make that story or that argument of what you contributed.

John Mamola: It’s been five years since you returned to the world of radio management. What are your aspirations for the next steps in your career?

Chris Oliviero: This might be career suicide if I put it this way, but I’ve honestly achieved what I was looking to achieve. I started as an intern for The Howard Stern Show in the mid-’90s, but I was rejected for an internship at WFAN a couple of days before I got that internship.

Growing up, the most influential moment in my young life that got me to fall in love with radio was July 1, 1987, when WFAN signed on—the first all-sports station in America. I was in grammar school at that time, and fell in love with the format, the medium, and the station.

I became a fan boy and would write letters to Steve Somers. I’d call into Mike and the Mad Dog.

So, if you asked that kid if one day he would have been the general manager of WFAN, I would have said, that’s good enough for me. Anything that occurs past that or after that is house money.

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.