Ten years ago, while working as a reporter and host for NBC and the NFL Network, Alex Flanagan parted ways with her agent, longtime sports media representative Sandy Montag. Now, she serves as the Vice President of Broadcasting at The Montag Group: A Wasserman Company, where she also works as a sports media agent.
“In an odd twist of funniness, Sandy was my agent at one point, and I actually fired him. And now I’m working for him. So who has the last laugh,” Flanagan tells Awful Announcing in an interview this week.
Flanagan changed agencies in 2014 when she was working several high-profile jobs for NBC and the NFL Network. As her longtime roles with Notre Dame football and Football Night in America went elsewhere, Flanagan was going through a difficult time in her on-camera career. And it’s an experience that has guided her in her new role as an agent where she now helps to advise the careers of broadcasters all across the sports media world.
“The upside is I believe every experience is meant to teach us something. And that whole experience taught me about navigating relationships and complex dynamics and as an agent it now serves as a constant guide for me, allowing me to make more informed decisions and approach my client’s career challenges with sensitivity. I am very hands-on with my clients. As their representative, I see my role as being approachable, responsive, supportive, collaborative, and just like I did when I was a reporter,” Flanagan reflected.
With her reporting career at a crossroads, Flanagan began pursuing the agency side. That first led to The Familie in 2019, an entrepreneurial startup where she did everything from taking out the trash to hiring general counsel and launching a media department. For the longtime host and reporter, moving out from in front of the camera allowed her to chart her path forward in a new way.
“I think it’s a hard business to age in as a female,” Flanagan said. “It can be challenging to have children and want to be home and be part of their sporting careers as well. Having three kids and being on the road a lot, I think, like many people’s careers, there’s peaks and valleys. I had numerous peaks and a few valleys that were really frustrating for me and eye-opening about the business.
“I also wanted to be able to control my own destiny. As an on-air talent, it’s a very subjective business, and you can be really good at your job, and if somebody doesn’t like how you look or how you sound or have a belief or thought about you that you’re not good, you can not get the good promotion or story or assignment.”
When Flanagan was hired by the NFL Network in 2006 shortly after its launch in 2003, it was a different time in the business. She recalled being the first woman in the studio with no dedicated makeup artists or wardrobe personnel to work with women. Her resume at NBC included stops at Thursday Night Football, Notre Dame football, the Olympics, and the Super Bowl. Now, as an agent, Flanagan shares that experience with her clients and the realities that women in on-air roles still face today.
“For me, there was a little bit of exhaustion in focusing on what I looked like and dressed like,” she says. “As you age as a woman trying to stay young there is a lot of pressure in that aspect of the business. I also got to a point where I was really blessed to have done so many amazing things – multiple Olympics, a lot of Super Bowls, on the sideline for history-making events.
“I really loved that and was so appreciative of what I got to do, and I think I was ready to try a new challenge and to take some of all of that that I had built and see what I can do in the next twenty years and make an impact in another area of the business. I feel like I’ve found the best of both worlds where I can live vicariously in some ways through my clients and get some of the excitement that I got when I was doing it on-air but also get to use a lot of my knowledge and resources to apply it to their careers.”
After four years at The Familie, Flanagan joined The Montag Group in 2023. The Montag Group is the sports media and broadcasting representation arm of Wasserman’s broad sports, music, and entertainment portfolio. Her clients include a diverse array of broadcasters, from hosts and reporters to play-by-play announcers and personalities from UFC to WWE to NASCAR and the NFL.
Flanagan’s first broadcast client is current ESPN contributor Kimberley A. Martin, an experienced NFL writer who can now be seen on Get Up and First Take, giving Stephen A. Smith and Chris Russo an amazing collection of facial expressions while providing her expert analysis about the league.
Flanagan reflected on the progress that has been made for women in the sports media industry since she was reporting and helping to raise a family. She sees that it’s different now for many of her clients who have had or are having children compared to when she recalled working a Super Bowl and feeling the pressure to downplay that she had just given birth to her third child weeks earlier.
But in spite of some steps forward, there are still boundaries around what women are perceived to be able to accomplish in sports media, especially as they advance in their careers. While experience is often seen as an asset for men in the sports media world, with some working for several decades, women are often not afforded the same opportunities for longevity.
“Openly, I see women now on social media talking about kids and their families. That’s changed a lot,” Flanagan said. “There’s still a lot of limiting beliefs around where women belong in sports. We’re slowly seeing more women placed in roles like play-by-play and even analyst. They’re few and far between. Women are still largely relegated to sideline jobs or roles that have traditionally been ways to get a female presence in a broadcast.
“We still have a long ways to go when it comes to ageism. A lot of times, when it comes to where we put women on a broadcast crew, it’s often the lowest-paid position, the most disposable position. We have to find ways to make those positions more valuable and utilize the experience and the resumes of women who are in them.”
Using her many years as an on-air personality allows Flanagan to share those unique insights with those who are now in the same position. Whether it’s the highs and lows of a career in broadcasting and coming to a crossroads, the unique pressure that women face, or the ins and outs of reporting, Flanagan said that she tries to be as involved as possible in her agency work.
“It’s been really helpful, everything from continuing as a working mom and how to balance that with this job that requires a lot of travel and a crazy schedule to how to write a sideline hit where my clients will use me as an editor,” she adds. “Other people, I’ll strategize how to approach a job or their career. I’m very actively involved in the day-to-day of their lives, knowing that I get it, and a lot of people they’re dealing with were either my bosses, my producers, or production assistants. So I have a real working knowledge of those people and the challenges they’re dealing with based on different personalities or different job requirements.”
Flanagan works with clients, network executives, and producers who used to be her colleagues on the other side. Seeing the sports media world from both the on-air and agent side of things gives her a perspective that not many in the sports media realm have ever been able to see. As her second career continues to grow, she hopes to be able to apply what she learned from being a reporter and an agent to lead to positive change in the profession.
“The business has a lot of room for change,” said Flanagan. “It’s typically been a very transactional business, and it was for me when I was represented by agents. I really want it to be more of a partnership between me and my clients. Far too often, on the transactional side, there are very limiting beliefs on what talent can and can’t do. I’ve always laughed at it because who am I to tell you what job you should or shouldn’t be doing or what dream you can or can’t have? I’m really focused in this new career of mine on abundance, and having a growth mindset, and applying that to myself and my clients. I don’t think placing limits on clients is advantageous in this business.”
As for her career, Flanagan’s goal is to reach the same heights as an agent as she did as a broadcaster.
“I’m a very competitive person by nature,” Flanagan continued. “I was very blessed to reach the pinnacle of my career as a sports broadcaster and get to do some of the most prestigious events you can do. I have the same goals for myself as an agent. I want to be the top agent in broadcasting. I want to revolutionize and change the way the business is done and change the way agents look at the business and operate.”
