“We need more younger women to aspire to roles that are traditionally male-dominated,” CAA’s Co-head of Basketball tells Boardroom.
As more NBA players attempt to emulate superstars like LeBron James, Kevin Durant, and Steph Curry in building business empires off the court that will extend their legacies far beyond the ends of their playing days, the role of a player’s agent has only grown more vital. And as they make some of the most crucial, significant decisions of their lives, more and more players are trusting CAA’s Co-head of Basketball, Jessica Holtz Steinberg.
Holtz directly represents Devin Booker of the Phoenix Suns and Karl-Anthony Towns of the Minnesota Timberwolves in addition to working with Chris Paul, D’Angelo Russell, Paul George, and Mike Conley. Thriving as a woman in a male-dominated industry is a substantial achievement in itself, but she’s also the first woman ever to two rep two max-salary NBA players.
That’s historic. And despite her insistence on staying dialed in and going to the greatest lengths for her clients at all times, she doesn’t downplay the significance.
“Obviously I understood how big that was, because it’s different. And it wasn’t something that I had or they had seen before,” Holtz said. “That’s one moment that I take to understand the gravity of it. But for the most part day-to-day, it’s what we know. For both [Booker and Towns], I’ve been with them for their entire careers. So my role in their worlds and my role supporting them is normal to us. But I do understand the responsibility that comes with being somebody that’s breaking a glass ceiling in a way.”
“And hopefully, that paves the way for other females that want to do the same.”
Holtz graduated from Penn State with a degree in sports journalism and remains a big Nittany Lions fan. She received her MBA from Baruch College in New York, and after interning with the NBA, she started out in the basketball industry by working at the league’s headquarters beginning in 2007.
That experience provided her with a great base of institutional knowledge and an ever-expanding list of contacts, and over the course of her four years at the league office, Holtz realized she wanted to do something for herself. Something that felt more entrepreneurial, focusing on individual players rather than the 450 who play in the league holistically. And in 2011, she made the jump to the sports agent world with Excel Sports Management.
Holtz quickly rose through the ranks at Excel, becoming their senior director of marketing before moving over to Creative Artists Agency’s CAA Sports in 2014. She notes the agency’s impressively broad reach, support systems, and influence across sports and entertainment as a major reason she was drawn to CAA.
“If I was going to try to be at the top of my game,” Holtz said, “I was going to need the support and the resources that would allow me to best work with players that had dreams where the sky was the limit.”
Michael Levine, one of the two co-heads of CAA Sports, said he knew very early on that Holtz had the “it” factor to be a difference-maker in the industry.
“We felt like Jessica was the perfect fit for us and our culture,” Levine said. “Her motor runs at a high level always. She has great EQ — emotional quotient — and really works well in understanding a room and a situation, whether that be with colleagues or with clients or potential clients. And from the outset when we met, she was clearly deeply versed in player business and the NBA ecosystem. It didn’t take long for us to see that she was going to be a major contributor for us as we grew.”
Holtz credits Levine and fellow CAA execs Howard Nuchow and Paul Danforth with constructing a collaborative, empowering community within the basketball division. Leon Rose, the head of basketball at the time, was another key mentor of hers, someone who allowed her to do what she was good at and expand her role at the ideal pace over time.
“Despite his stature in the industry and all the incredible things he’s represented over the years, he allowed me, a younger woman in my 30s to do what I was good at,” Holtz said of Rose, who became president of the New York Knicks in 2020. “And if that meant me having a conversation with our clients instead of him because it was better coming from me and how I work day to day, there was no ego there. And he just sort of talked to me, would give me guidance, and allowed me to do a lot of things that maybe someone else in his position wouldn’t have just because he believed in me.”
Rose let Holtz listen in on contract conversations despite being a marketing agent, placing her alongside NBA team executives, running point on different projects and building key relationships that would allow her to continue to learn and grow.
And ultimately flourish.
“It wasn’t like we were supposed to stay in our lane,” she said of her working relationship with Rose. “It was ‘hey Jess, you’re welcome in my lane if it’s going to be better for the client.’”
When Rose left CAA for the Knicks, there wasn’t necessarily a grand meeting or meticulous series of conversations about what would happen to his clients; it was more about going to the players and asking what they wanted and what was best for them. And for Booker and Towns, Holtz was the best person for the job, and the heads of CAA Sports concurred.
Holtz became certified as an agent with the NBPA, and soon made history as the contract agent for two max players — but it was all part of what she described as a natural evolution, as she was already working with Booker and Towns day-to-day as they navigated the business side of sports.
“She cares about our business and her clients in a way that’s really personal,” Levine said, equating the level of care for her clients to older siblings looking after, caring for, and protecting their younger ones. “She’s as committed to getting the job done for her clients as anyone in our organization. And that commitment and that real passion for the work has translated to an impact with those players that gives them the comfort level that they need to trust her in a way that is a vital ingredient to a successful agent-client relationship.”
And everything Holtz does on a daily basis, from maximizing her clients’ income to developing an infrastructure around them and helping to build their businesses, is to make their lives better. Specifically, she’s worked with Booker to secure key endorsements are with Nike, Foot Locker, and Finish Line, as well as a notable investment in Overtime. He also won the NBA’s season-long Community Assist Award for his charitable expert in the Phoenix community, an achievement Holtz said he takes as seriously as his accomplishments on the court.
“That’s not just a quick transaction, ‘show me the money and I’ll see you again in a few years when your contract’s up,'” she said. “It is very much a 360° representation and figuring out new ways to make money. You’re seeing athletes want equity in businesses, not just signing endorsement deals and stand in front of a billboard. So agents nowadays have to be really good at following those interests, getting ahead of trends, and providing services that support the players’ manifold interests.”
“It’s about seeking out and finding experts and putting them in place to support her clients in building their businesses and brands both on and off the court. It’s about having the emotional intelligence to find out what people are going to work best with and for you to help achieve those clients’ goals and objectives,” she said. “How we do maximize your opportunities off the court in a creative way that best supports you? And my involvement is to try to figure out the right pieces around us and go from there.”
While her role representing Booker and Towns feels natural to her and CAA, Holtz said she understands the responsibility that comes with breaking a glass ceiling as a woman agent representing superstar athletes. It shouldn’t matter that she’s a woman — but thinking about the word “representation” in a different way, we absolutely need more role models like Holtz here and now.
And she’s hopeful that she can pave the way for other women who want to break into the industry.
“Women like Jessica blaze new paths, and younger executives and younger women are going to realize that they can be just like her,” Levine said. “She’s terrific and we’re so proud of the work she has done for our company and our clients and we also are even more excited about what lies ahead for her. Because we really feel like she’s just begun to scratch the surface as a powerhouse in this industry.”
While Holtz wishes her role as an NBA power broker didn’t feel like an anomaly, she knows that, quite frankly, it is.
“It’s not just professional sports. It’s a lot of boardrooms and a lot of power positions across a lot of industries that are traditionally male-dominated,” she said. “And I think that the reason we’re having this conversation right now is because I am doing something different. And we just need more people to do different things, and for more younger females to aspire to roles that are traditionally male-dominated.”
Holtz often says that seeing is believing. And she thinks the dearth of female agents in professional sports is brought on by not seeing them in those positions very often. What she wants to do is let people know and understand that this is possible.
That if you put your head down and work really hard and align with the right clients and business partners, that they can get this done too and become the next Jessica Holtz.
And when the next Devin Booker or Karl-Anthony Towns comes along in the NBA, it won’t be such a huge deal that they chose a woman as their partner in navigating the most important professional decisions and life choices.
“We need to think about these roles as positions that men and women can do or would be good at,” she said, “versus it being something that’s a really crazy choice or something that people wouldn’t imagine before.”