Kelli Masters never set out to be an NFL agent. As an undergraduate at the University of Oklahoma in the early 1990s, she performed at Owen Field during half-time as a baton twirler and got to know the Sooner football team, developing a greater love for the sport. She stayed in Norman for law school, studying business and nonprofit litigation. Becoming a sports agent simply never occurred to her—perhaps that's not surprising, considering there were almost no women in the industry at the time.
While practicing at a law firm geared toward helping nonprofits, Masters was contacted by Josh Heupel, a former Sooners quarterback, who reached out to her with legal questions about his #14 Foundation. As Masters advised Heupel, word spread that she specialized in the legal side of nonprofit endeavors, and inquiries from other former football players and their families began rolling in. Meeting each new person, Masters would ask a simple question: "Has anyone asked you what your goals are and what you want your legacy to be?"
As she talked and worked with athletes, she saw where they struggled, and that quite often they were surrounded by people who didn't have their best interests in mind. It was a moment of awareness that sparked a career change.
"Players are often seen as expendable, and as assets or paychecks," Masters said. "So many agents enable bad behavior in their clients and then these kids are often left worse off financially and physically once they leave the NFL."
She decided that she wanted to help athletes, and provide them with more guidance than they were getting. "They are adults put in unique circumstances with unique platforms," Masters said, and her job, as she sees it, is to set them up for success by setting up some expectations. "A lot of these players don't know how to be adults because they're used to having everything done for them."
Athlete representation is a cutthroat business, with a lot of promises and money being thrown around, sometimes with little care for players' well-being. It's also heavily male-dominated. When Masters became a NFL agent in 2005, there were 1,150 agents certified by the NFL Players Association; only 30 were women. (To become certified and represent NFL players in individual contract negotiations, agents need to submit an application to the NFLPA and pass a written exam.)
She knew she was entering a man's world; one prominent agent told her straight out that women had no place in the industry. But while some initially believed that Masters' gender was a disadvantage, it has proved to be one of her most valuable assets (and that particular agent would eventually become one of her greatest mentors and advocates).
"Most people saw being a woman in the NFL as a weakness, but it actually opened up a lot of doors for me because many were curious why a woman would want to work as an agent in the NFL," Masters said, which helped her to score meetings with scouts, personnel directors, and general managers.
"But once those doors opened, I had to make the most of those opportunities—by knowing how to talk shop and communicate effectively about my players and the business."
In 2010, she made history as the first woman to represent a first-round draft pick with defensive tackle Gerald McCoy, who was selected third overall by the Tampa Bay Buccaneers. "Women are fighters," McCoy told ESPN the following year. "They have that mom instinct. With a man, it might be a little bit about himself, but I have seen it first-hand with me how she battles. Believe me. I've seen her go to battle for me.''
Today, Masters is one of seven women agents with active players in the NFL, according to the NFLPA. Her agency, KMM Sports, has six players currently on rosters, and represented four more at the 2016 draft. Her story, however, is not simply about the challenges facing a woman on her way to becoming a respected sports agent. It highlights how the NFL should be recruiting more women in all areas of the game.
"The industry is changing, albeit slowly," said Kristen Kuliga, who in 2001 became the first woman to negotiate a starting quarterback's contract, Doug Flutie's $33 million deal with the San Diego Chargers. She saw something special in Masters, whom she encouraged but also warned that, as a woman, she was choosing a very tough career path.
"There still aren't very many women agents, so young women that are in school or law school don't know it's something that they necessarily can do. And you don't know you can do it unless you see others similar to yourself doing it."
Both Masters and Kuliga noted that sports agencies have failed to counteract this with specific initiatives to recruit women and change the gender imbalance, which Kuliga believes makes women hesitant to even try.
"The larger agencies have been founded by men and it's mostly men working at these agencies, and people tend to hire people like themselves," she said. "I don't think it's purposeful discrimination by any means; it's just education needed to highlight that women can do this business and embracing women to be part of the business."
And that is why, she added, Masters' success is so important—she's a beacon to other women.
In fact, that's partly how I got the idea to write about Masters, who I'd recently become acquainted with, in the first place: I was visiting a college friend of mine, Katie Saucier, who had just graduated from UCLA Law School. Katie mentioned that she would like to get into sports law, and when I asked about Masters, her eyes immediately lit up.
"Are you kidding? she said. "She's one of my biggest role models and reasons why I want to get into sports law."
Katie played golf at the University of Washington and also served on the school's student-athlete advisory council. She first read about Masters at law school. "She wants her athletes to make an impact in their communities and to achieve goals beyond their sporting career. That struck a note with me," Katie recalled, "on why I was initially drawn to one day becoming a sports agent."
Like Kuliga before her, Masters mentors women who want to enter her field. Jametta White had been practicing law for close to ten years when she decided to become an agent; someone put her in touch with Masters. She was surprised at how invested Masters was in her success.
"Being a female in a male-dominated world, there are very different challenges you have to face that men do not understand," said White, who got certified in 2012. "Having someone in my corner helped me deal with the obstacles I would face initially, like being asked if I was too pretty to be an agent."
Those kinds of questions, one would hope, would disappear as more women joined the ranks of agencies. And if the ethical argument isn't convincing enough, there's the economic one: study after study after study after study suggests that more gender balance in the workplace makes organizations more productive and more profitable.
This is perhaps why the NFL has increased its own efforts to recruit and promote women. (Another reason? The fact that women make up an estimated 45 percent of football fans.) Most recently, the league named Sam Rapoport its director of football development, a role, she announced, that would "create that pipeline for females to enter into positions that were traditionally held by men," such as scouting and coaching roles.
Here, too, the obstacles are slowly dissolving. Last year, Jen Welter became the first female coach in the NFL with the Arizona Cardinals. This season, the Buffalo Bills hired Kathryn Smith as a full-time quality control-special teams coach. Women hold 30 percent of front-office positions, according to ESPN, and include league executives like CMO Dawn Hudson, but football operations is still largely a boys' club.
Kuliga believes that agencies need to get on the same train as the NFL and realize "that A) we know the game just as well, B) we can talk the game just as well, and C) negotiate just as well. We bring a different of negotiating to the table."
To that end, Masters organized her first Celebrating Women of Football event last year at the Super Bowl in San Francisco, inviting notable women from all areas of the league, such as Welter.
"For Kelli to be such a forward thinker and put that event together so we [women] could all connect and share our stories and what brought us on this similar crazy path in the sports world was really impactful," said Debbie Germain, an agent based in California who attended the forum earlier this year.
Like many of the women I interviewed, Germain had never intended to become a sports agent, but it was her love of football that eventually pushed her into a new career path. While attending college at San Diego State University, she said, "I was the girl who was the stat girl for the team, not the cheerleader." She also tutored football players.
Years later, after having two sons and taking them to sporting events every weekend, she reconnected with one of her former tutoring students, who had gone on to play in the NFL after SDSU and now had kids of his own. He asked her, "Why don't you become an agent?" and what had once been a family joke (Germain's husband would playfully suggest she find a way to make money off her passion "since you're always in the sports pages with our kids" anyway) became a serious venture. Germain became certified by the NFLPA in 2012.
For Germain and White, Masters is an inspiration for taking a chance on herself and showing that it is possible for women to be successful in the industry while also supporting each other. In fact, the two women, who met at the Women in NFL event, are now working together to sign a player.
As for Masters, her approach as an agent has evolved over time, but she remains dedicated to her original cause of helping transform the lives of her players in a positive way.
"In the beginning, I was willing to take on responsibility for things that really weren't my responsibility," she said. "Now I think it's a matter of communicating effectively in the very beginning about what players can expect from me and also laying out my expectations for them."
These basic expectations range from returning emails and phone calls to showing up to appointments on time. Those things, she says, help her and the player work together as a team. Through creating those boundaries and expectations, she learned that she earned more respect from her players and they valued her work more.
Today, Masters has expanded her agency to include athletes in a number of sports, not just football. She represents baseball players, an MMA fighter, and three Olympic athletes, including Johnny Quinn, a NFL player who went on to compete as a bobsledder in the Sochi Games.
"I guess I just like challenging myself," she said when asked about her new clients. "I wanted to see if I could do it."
Another bobsledder, Olympic silver medalist Aja Evans, was looking for an agent when a friend who played in the NFL recommended Masters. After their initial meeting, Evans knew she was the one.
"Kelli is a really strong woman. I loved how she dominated her field in football as a female, and despite transitioning into Olympic sports and bobsledding, she was still very strong-willed and determined. That instilled a lot of confidence in me."
As an agent, Masters has had to play many different roles—cheerleader, parent, travel agent, counselor, negotiator—but one in particular has taken her more time to settle into: that of a role model.
As her quiet climb up the industry ladder gained more attention, and after one espnW article in particular, Masters received a deluge of emails, calls, and letters from women all over the country touching on how she inspired them to become agents.
"Before then, I would hardly do interviews," she said about the article. "I couldn't believe how much it inspired other people, so it made me more willing to talk and share my experiences. Because of that, I feel like I'm where I'm supposed to be and doing what I'm destined to do right now…. The main question I ask myself everyday [is] 'Am I still doing this for the reasons I started?'"
The answer appears to still be yes.
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