She was named one of the Most Influential Women in Radio in 2017. 30 days later, she was fired from her role as Chief Revenue Officer.
The sudden and unexpected termination forced Heather to reinvent herself and build her brand from scratch.

Now, Heather has authored her first book, Confidence Creator, has been featured on the Elvis Duran show, and was named a Brand Ambassador for Perry Ellis International.

Find out how she climbed her way back to the top, how you can become a better salesperson and leader, and so much more in this week’s Conquer Local episode with George Leith.

Heather’s book, Confidence Creator, is available now on Amazon.


It’s another edition of the Conquer Local podcast. About five years ago, I was at the National Association of Broadcasters Convention in Vegas and I had booked an appointment over LinkedIn. So, it was a cold, LinkedIn reach-out to a woman named Heather Monahan, and she was the Chief Revenue Officer at Beasley Broadcast. It was a group that…they had radio stations all over the U.S. I wanted to get a meeting with her to pitch her on the Vendasta platform. And she said, “By all means, I would love to meet with you. We’re looking at new digital solutions. Where would you like to meet?” And I was told by consultants that we were using at the time, “The place that you meet is at the Wynn.”

And so, there we are, we’re meeting at the bar at the Wynn, at 11:30 on a Wednesday morning. And in walks Heather Monahan and her VP of sales in Las Vegas, Cory Cuddeback. And we sit down at this table, and they ask me to give my presentation.

And usually, I’m used to giving a presentation with a laptop but I thought, “Well, I only get one shot at this and I have 25 minutes apparently, to make this presentation.” And halfway through the presentation, Heather looks up at me, and I don’t really think she was paying attention to me at that time because she was on her phone and she says, “What’s the reason we should work with you and not with your competitors?” And I said to her, “Because you get me!”
And both of them looked at me and said, “That’s good enough for us, come on over to our station and let’s get started.” And that’s how our five-year relationship was born. And about a year and a half ago, Heather left her position at Beasley Broadcast and she had embarked upon building this brand, the Boss in Heels.
So, we’re gonna bring a boss in heels on to the podcast in a few minutes’ time and talk about how she’s building her personal brand, how she’s rebounded from being fired from her job of 14 years. And some things that you can do if you are faced with adversity, and some suggestions for you as a local sales rep. All that’s coming up next with Heather Monahan, author of “Confidence Creator,” on the Conquer Local Podcast.

Bringing Her Game Every Day

George: What a great pleasure to have Heather Monahan, an old friend of mine from Miami, Florida joining me. Author of “Confidence Creator” and the Boss in Heels on the line. Heather, hello, welcome to the podcast.

Heather: Hi George, thank you so much for having me.

George: Heather and I have known each other over the past five years and we’ve worked together when she was involved in the radio business. And Heather, let’s talk about that first. When you and I met you were Chief Revenue Officer of Beasley Broadcast Group, and I wanna talk about what it was like leading a team of high-performing sales professionals. You know, what sort of a game did you have to bring on a daily basis when you were in that role?

Heather: You know, it’s challenging because, you know, media is so competitive these days, so it was really challenging to ensure that I was able to retain my top talent and those really high-level performers, as well as continue to help them grow and advance, and stay close to the ground and close to their day-to-day fighting local so that I never got too detached and wasn’t aware of what they were really dealing with. So, it’s definitely not an easy job.

George: You know, my buddy, Cory Cuddeback, who is leading sales in Las Vegas told me one day, I know we were going out to see a customer, he said, “You know, I really appreciate Heather’s leadership because I can just phone her with any problem that I have and she always had a bit of advice for me.” And Corey is a top-performer. You’ve really got to be in touch and have a lot of respect from that group to get the kind of feedback, I found.

Heather: For sure. And so, I think that the key there is making sure you stay close to that hand-to-hand combat on the streets because when you become detached from that, and I’ve seen it happen with a lot of leaders over the years in various industries and companies that I’ve worked with, you really can’t relate to your team. And when your team is no longer relating to you and feeling that, you know, you really understand and have empathy for their situation and can help, advise, and coach them through the challenges, you really don’t bring a lot of worth anymore.

Advice for salespeople in today’s competitive environment

George: Do you have any advice for local media salespeople or digital salespeople on things that they should maybe, be doing a little bit different in this competitive environment that we’re in today?

Heather: For sure. You need to define a unique value proposition, and you need to define that about yourself and who you are as well as the products and services that you are approaching a client with. And when you’ve really fine-tuned that pitch, you’ve got to practice, practice, and practice it over, and over again, so that you can seamlessly explain that to someone in a very quick and introductory fashion so that they can see your value. When people are being bombarded with salespeople from 20 different organizations in a day, what is gonna set you apart? And you need to be able to answer that question. That’s really critical.

The other critical piece of advice I would give anyone, and this goes for, just in life, in general, or selling and media, you need to be able to get to the ultimate decision-maker. And there are a lot of ways to do that, but one of the best ways, I’ve found, is through connecting through a common link, a common person, a common thread, so that you’re almost getting advice through somebody else or recommended through someone else. Then, typically, that person will take your phone call and will be willing to meet with you.

Building her personal brand

George: Yeah, that warm intro. You know, you are a social media expert because you’ve been building your new brand. Tell us about the new brand and, you know, where your career has taken you because when I was going through the book, it talks about your departure, and we’ll get to that in a moment, but let’s talk a little bit about how you’ve built that brand and some of the tactics that you’ve been using to build your brand online?

Heather: So, a few years ago, I realized that my biggest challenge as a chief revenue officer in radio was I could not attract good talent. And you’re only as good as your people. So, if you’re struggling to get amazing people in the organization, you’ve got a big struggle. Well, it came down to this for me. I figured out that once I met people and created a relationship with them, they would want to be a part of my team and a part of what I was doing. But it took so much time to make that happen. It was me going out and chasing down 20, 50,100 people. I needed to flip that script and get a platform and a situation where people were coming to me and I was able to show them who I was so we could have that connection point and that interest in one another.

And I realized it was really the advice that I had been giving all of my clients which was, “If you wanna target a different demographic, a different audience, and scale it, you need to be on digital platforms, you need to have a social presence, you need to have a website that’s optimized, and you need to have SEO and SEM, and you need to have reputation management.”

So, all of these things I was selling to my clients, I never thought about implementing for myself. So, when I decided to flip that script and instead pull people towards me, I launched my personal brand so that people could get a chance to know who I was and get to know me before I was chasing them down and trying to get to know them. And that was really the start of Boss in Heels.

On stage

George: So, that brand continued to grow. And I remember seeing you speak at Gordon Borrell’s convention two years ago. You’ve always been a great public speaker, give us some tips as to what, you know, you recommend to those presenters that are gonna stand on stage or stand in front of a group of clients or a Chamber of Commerce to make a presentation. What are some tips that you can give them?

Heather: Sure. So, one of the most important things is you wanna be authentic and real. And, as long as you can tap into who you are and what’s unique about you, you’re going to be more confident when you’re speaking. So, really, you know, getting to know yourself. And if you’re a funny person, you’ve got to incorporate humor when you’re speaking. If you’re someone who’s very empathetic and understanding, you wanna share personal stories around those topics. So, creating an intro or a beginning to a presentation where you share a personal story, no matter who you are, you know, around you and your unique personality, that’s really gonna connect the audience to you and catch their attention.

So often, people present and they are forced, and cold, and detached. It doesn’t matter what material you’re presenting, as long as when you intro you make it personal and relatable. And by being yourself and sharing a personal story that is a phenomenal way to begin any type of a presentation. Another technique that I use, especially when you’re in a dry material environment or, you know, full-day meetings and seminars, is to call people out occasionally, in the presentation.
So, I might say, you know, I’ll give a personal story intro and talk about why something is meaningful or why I’m there today. And then, during the presentation, I’ll say, “Jim, you know, you remember when this happened to you,” or “Am I the only person in the room that’s ever struggled with this topic?” And I’ll raise my hand and so that I’m trying to get everybody else to engage and raise their hands.

So, really having that back and forth with the audience is helpful and it gets their attention. Most people are looking at their phones and not necessarily, engaged with you the way you need them to be. So this is a way to re-engage them and make it more exciting and fun for the audience.

George: Well, I appreciate that. That is 4 of what is 10 items inside the book on giving a great presentation. So, thank you for that. it’s actually, like, Chapter 29 if my memory is correct.


Now, let’s really dig into some of the meat and potatoes of this book, “Confidence Creator,” because, you know, you ended up getting fired from your job as chief revenue officer, you’d had that job for quite some time. And you’re very transparent about what that meant to you and how it felt. Can we talk a little bit about that?

Heather: Sure. That was terrible. I definitely am a Type A, overachiever. I’ve won a ton of awards, a lot of accolades over my career, and I’ve never been fired, I always get promoted, So, for me, to get fired once I had reached the C-suite, as a woman, and a successful woman who was really achieving so much. I had just been recognized as one of the most influential women in radio literally, 30 days before I was terminated.

So, to say it was shocking and mind-blowing is an understatement. I was beside myself. I didn’t know what to do. I had been there for 14 years, and that was the work that I knew, the team that I had built, and I didn’t want to leave. I was pushed out. I was told that my position was no longer needed in the company, which was very hard for me to swallow.

So, you know, those first few days after being terminated were devastating and a lot of tears, a lot of Chardonnay. And eventually, I decided to, kind of, take a step back. And it was my fiance that really helped me to do it. He said, “So, what do you wanna do? Let’s think about it. You can do anything in the world. You’re such a capable person, what do you wanna do?”

And immediately, like everyone, I thought about the world I know. So, “Oh, I should probably go to a competitor and go right back to what I was doing.” And he asked me a great question. He said, “Is that what you really wanna do?” And I had to think about it for about a minute and said, “No, it’s not. I’ve been doing this for 20 years and I’ve reached the highest levels. I know exactly what it’s like and about, I’m not growing anymore. Why don’t I take this chance in my life to go out and just jump off that ledge and try something completely different and just really, believe in myself and believe in, you know, my network, and my skill set, and my talents, and just go for it.”

And that’s what I ended up doing.

Reinventing herself

George: Well, you know, it’s a very inspiring story. Inside the book, you really go through a number of different challenges that you had throughout your career, and then you rose to the pinnacle, and then you had to make that decision to try something new. And we’ve got author in there, you’re a brand ambassador for Perry Ellis. What other things is Heather Monahan up to today, as part of this new path that you’ve taken?

Heather: Oh my gosh, it’s crazy, and I can’t keep up with myself. It’s so intense and fast-moving, but so many opportunities have come to me since I made the decision to go out on my own, and it’s really been overwhelming and encouraging. And I really hope people who are listening to this can remember that when you start taking steps towards doing something new and doors keep opening, I’m not saying they’ll all open, because they don’t, I’ve gotten plenty of rejection in this space, just like I did in the radio space, but I started noticing really, unbelievable, opportunities presenting themselves and finding solutions that I didn’t know existed. Because while I might have been a senior-level leader or a high-level accomplished leader in my old life, in this new life, I’m a beginner. I’ve never owned my own company, this is a first. I’ve never written my own book.

So, all of this is really new and, you know, with anything you don’t have a lot of experience in, you’re gonna have failures and you need to overcome those failures.

So, along this way, I didn’t have a very clear path. I had a vision in my mind what I wanted to accomplish, which ultimately, is I want to give everyone out there the power to create their own confidence and elevate themselves and know they are not alone, because I’ve been in almost all of the ditches that are possible, and that’s why I was so transparent in my book. But, you know, along the way, writing the book, which was my first step, a consumer packaged good company came to me and wanted to partner with me to develop products for women that were empowering, and around my messaging, and affordable, so that everyone can have access to a number of different quality products to elevate them.

Then came an opportunity from a video company who taught me the business of video teaching, and technology, and the opportunity with taking what I was teaching in my book in advancing it even further and creating courses.

So, I’ve been working on so many different products, so many different concepts. And, you know, again, the road is not clear to me moving forward, but it continues to appear as long as I keep taking actionable steps forward.

Elvis Duran; Ivanka Trump

George: Well, as somebody who is also working on my personal brand, I got to ask a question. I just don’t understand how the hell you’re getting all this amazing press. Because I go to Instagram or I go to LinkedIn one day, and here you are on the Z100 morning show with Elvis Duran. How the heck did you get that interview? That’s incredible publicity.

Heather: That was crazy. And, you know, that really came out of being transparent and asking for help. So, one of the key things that I did when I was terminated was I put it out on social media. And so many people told me that, that was an epic fail and that I shouldn’t do that, and it made me look bad. But the reality was, it was the smartest thing I ever did in that moment. It created an opportunity for hundreds of thousands of people to see I was available and I was asking them to help me.

One of the people that responded to that post was Froggy from Elvis Duran. And he saw the post and sent me a DM and said, “Hey, if there’s anything I can do to help you, I’m here for you.” And I responded and said, “Yeah, I’d love to come on the show.” And he said, “Okay.”
George: So, if that’s not enough, I see you on the CW, I see you on a number of other programs, but let’s talk about Ivanka Trump and how you ended up getting that Twitter message and involved with her. How did that come about?

Heather: That’s funny. So, I had someone representing me for PR to promote my personal brand. And she had reached out to Ivanka, had women who work website and community, supporting women and trying to help them advance in the workplace. So, the PR woman reached out on my behalf, pitched me as a potential interview. They liked what I represented and they interviewed me. Not with Ivanka, but with one of her team members. And the interview went up, and the day the interview went up, I got an email from Ivanka Trump. And it was so sweet, but it was very apparent to me that it was a form email that she would send. And the reason why I knew that is because, somehow, there was a glitch, and instead of being my name it either had a blank or, you know, it was like, “put a name here,” kind of a thing.

So, it was one of those moments I thought, “Oh, do I let this go, I mean, this is Ivanka Trump, or do I say something?” Well, in my typical fashion, I said something. I definitely said something. I responded back to her and I thanked her and told her how grateful I was to have her support and exposure but I did want to let her know so that she wouldn’t make that mistake again, moving forward, that somehow there had been a glitch and that it did not come through as personalized, and that I didn’t want her to send any more emails out like that again.

She sent me back a real, personal email, and thanked me so much for, you know, being honest with her and letting her know what happened. And then she said, “If there’s ever anything in the future that I can do for you, please let me know.” So, again, when that door opened and someone was inviting, you know, they’re here to help you. You know, are you gonna do anything? I jumped right on it and I responded immediately, and I said, “It would mean the world to me if you would tweet about the interview that I did on your site. I’d really appreciate it.” And she did.

Balancing personal and professional

George: So, as a working mom, and your young lad just turned 10, and we just celebrated Mother’s Day. There is a very interesting title to one of your chapters which is Balance is… Can you talk a little bit about that, please?

Heather: Yeah. I think, in our society, you know, sometimes we believe, because there’s so much fake news and fake social and everyone appears perfect and happy on the weekends with their family, and happy at work during the week, and they always look perfect, that I really wanted to shine a light that, that’s not true, that is far from true in my life. And really, it’s far from true in everyone’s, regardless of who you are.

So, you’re always gonna feel, as a parent, at some point, that you’re letting one area of your life down. Whether it’s your personal health and development and taking care of yourself or it’s your sleep or it’s your work, and you’re just not putting in the hours that you need to or it’s your children and you’re not there for games, and tournaments, and doing homework. You’re always gonna feel that it’s not working out perfectly because there is no perfect solution.

And what, instead, I tried to look to to ease that challenge for myself is the hidden blessings that come out. And one time I was on a work trip, last year, and my son had a soccer game and I wasn’t there. And he was injured in the game. And his father had to be working as well, so neither one of us were there. And he was alone and hurt bad enough that he was crying on the sideline. And another mother saw him in that moment and ran and sat with him and helped him. And it was heartbreaking when I first heard it, but what I realized was it taught him there’s not just your mom and dad in your life, in fact, there are other people, just in the world, good people, that will rise up when you need them. And he got through it, and I got through it.

And those experiences and taking, you know, those positive messages that you can receive from difficult situations really helped me to realize that balance is bullshit, and it doesn’t exist, but there’s always something good that you can learn from any situation.

Building confidence

George: Well, the title of the book is called “Confidence Creator.” It really is a great 45 chapter-read that has all sorts of benefit to help people conquer local, I found. There is the stories of the struggles that you’ve had and the things that you’ve had to overcome. I really appreciate your transparency there. I think some people might have a look at you and say, “Oh, that’s a fairy tale thing going on there. And everything has been great for Heather, she’s never had any struggles.” So it’s great to see that. And, you know, we’re hearing that from more and more of our guests that, you know, success isn’t a straight line. It’s actually, this all over the place, kind of destination thing that you’re trying to go to.

But the other piece that I really like is just hearing these items around personal branding. I think that everybody could take that from the various pieces of the book. Tell us about when the book will be coming out and how people can get copies.

Heather: One of the reasons why I wrote this book is because I didn’t have confidence in my earlier years, and it took me a lifetime to figure out how to build confidence and create confidence. And I want everyone in the world to have that same blueprint.

You know, each one of these chapters are very small, they are personal examples of my low moments, in my life, and how I was able to figure out how to build confidence and how you can too. I’m so excited to tell you that, “Confidence Creator” is live on Amazon right now, and I have a limited number of hardbacks that were produced for the initial run because I self-published. It’s not a traditional publishing route, which is a whole other story and challenge. But going through, what I’ve done and created, everything has been a personal investment. So, I pre-ordered thousands of books but not 100,000, like Eden [SP] publishing might do.

So, I guess, we’re getting to the point now we’re going to sell out on our hardcovers. So, please, pre-order that book. It’s on Amazon right now, “Confidence Creator,” and it’s by Heather Monahan.

George: Well, it’s fantastic, Heather, having you on the show. It’s been a while since you and I saw each other face to face but congratulations, on all the new success that you’re having. And I appreciate you jumping on the podcast. We’re having a lot of fun putting this show together every week. We get listeners from all over the world and I’m sure that they are going to benefit from the content you’ve shared today. So, thank you so much.

Heather: Well, George, I mean, again, you have been such a great partner in business and a friend, reaching out and giving me this opportunity, I appreciate it immensely. So, best to you, and thank you so much for having me.


Well, what a great episode. You know, I respect Heather a lot. When she was fired, she absolutely is right in what she said, she went right online and she talked about it. And that’s where we live nowadays, in 2018. You’ve got to be transparent, you’ve got to call it the way that it’s happening, and guess what happens? All of these people reached out to help her elevate the next level of her career. She definitely, had built some brand equity over the years, 14 years of doing what she is doing. And you can see that in the growth that she’s having in her career today.

The book, it’s fantastic. As she said, it’s an easy read, but it reminds you of things that you need to be doing on a day-to-day basis. Plus, it talks about failure, how to deal with failure and that we should embrace it, and we should learn from it, and we should move to the next level.

As we continue to roll these episodes out, we’re thinking about you and the things that will help you. I’ve got some great teaching episodes on the way, in the next month, and we’ve been working on these over the past couple of months. We look forward to having your feedback, look forward to you getting your friends to subscribe. And please, reach out to me on LinkedIn If you’d like to speak more. I’m getting in-mails on a daily basis. I try to answer all of them as quickly as I can. And thanks to everyone around the world who’s listening to the Conquer Local podcast. My name is George Leith, I’ll see you when I see you.