Amy Trask and her path to becoming the NFL’s first woman CEO

Over the summer of 2019, SB Nation interviewed several women who currently hold or have previously held leadership positions within the NFL to find out more about them and the work they do. This Q&A series highlights the powerful women who have dared to shake up one of sport’s biggest boys clubs.

Amy Trask spent 30 seasons with the Oakland Raiders, including 16 years as Oakland’s CEO. Now, in 2019, she appears frequently on CBS Sports television shows like the all-female We Need To Talk and That Other Pregame Show. She is also chairman of the board of the professional 3-on-3 basketball league, Big3. In 2016, she released her book titled You Negotiate Like a Girl: Reflections on a Career in the National Football League.

Author’s note: This interview has been lightly edited for clarity and length.

Photo by Marla Aufmuth/Getty Images for Watermark Conference for Women 2018

SB NATION: You actually got your first internship with the Raiders by cold-calling the organization while you were in law school at Cal-Berkeley in the 1980s. How did that happen exactly?

AMY TRASK: I was in graduate school at the time, and after I started I saw that others were doing externships and internships. I picked up the phone and I cold-called the organization. I was patched through to a gentleman who very gruffly said, “What’s that?” and I said, “Well, I’ll work for you, and you won’t pay me.” He said, “Come on down” and he connected me with the person for whom I would be doing this internship with.

It’s very important to me that I add I am well aware that not everybody has the luxury of being able to say, “I will work for free.” I am very well aware and sensitive to the fact that not everybody gets to say that.

I did that internship roughly for two years of law school. There was no opportunity for full-time employment, so I took a job elsewhere.

SB: When you were hired full-time roughly a year later in 1987, did you have your sights set on eventually working in the Raiders’ front office?

AT: I had no plan. I didn’t have my eyes set on any particular goal within the organization. At one point, someone whose opinion I value and someone who I trust said to me, “You really need to have a five-year plan.” And I looked at him and I said, “I don’t want a five-year plan.”

I did not have my eye set on an executive position, let alone the CEO position. I was thrilled to be a part of the organization. I would and I did do anything I could to help the team. If I was told my responsibilities were to pick up the scrunched-up cups on the sideline, I would’ve happily done that. I was just thrilled to be with the team and happy in any role I could have.

SB: Describe what your job was like as Oakland’s CEO both from a day-to-day and overall perspective.

AT: One of the things I told people I loved most about my job was that no two days were ever the same.

[You] never knew because you could walk in with this terrific plan of what you were going to accomplish during the day and what you thought your day was going to look like, and either all hell broke loose and derailed you, or something sprung up. No two days were the same.

[I handled our] banking, our financial work, league compliance — I was the point of contact between the Raider organization and the NFL. I was designated officially, but also from a practical standpoint. I handled all of the league interaction, I handled NFL compliance, debt ceiling compliance, financing, banking, relations with the team’s limited partners. When [former owner] Al [Davis] decided at one point that he wished to sell some equity in the team, I oversaw that.

SB: Did you experience any challenges being one of the few women in an NFL front office in the 80s, 90s, and so forth?

AT: When I walked into my first league owners meeting, it was the first time that a woman who wasn’t the wife or the daughter of a team owner had walked into that room. It’s funny, people ask me all the time, “Were you nervous? Were you concerned?” And I thought, “No, because things like that don’t concern or bother me.” I was walking right in behind Al Davis. I was just fine.

I never spent one moment thinking about my gender, worrying about my gender. It always struck me, and frankly it still does strike me as just nutty. I could use a fancy term like counterintuitive, but just nutty. To walk into any situation hoping, anticipating, expecting that no one will be thinking about your gender if you’re thinking about your gender.

I don’t think it’s fair for me to walk into a room focused on my gender while expecting others not to be thinking about it. So I didn’t waste a minute of effort or energy on thinking about my gender. If other people wanted to waste their time, fine. Waste your time.

I’m asked all the time if I was tested because I’m a woman. The answer is, we’re all tested all the time. Whether it’s because of our gender, our race, our ethnicity, our age, our seniority, our educational background — we’re tested all the time. Well, what’s the best answer when you’re tested? Pass the damn test. So was I tested because I’m a woman? Maybe, let’s assume I was. And? We’re tested all the time. Worry about passing the test.

SB: What are some of the things you were most proud of accomplishing while with the Raiders?

AT: One was we were dealing with a very, very crucial, pivotal, existential business issue. And during that transaction, [it was] sleepless nights, and it was just very very stressful. And at one point I said to Al, “I don’t understand how you can sleep at night.” And he looked me right in the eye and said to me in the most direct sincere tone, “Because I have you, and I know you’re not sleeping at night, so I can.” And that was just overwhelmingly special.

When we concluded a portion of that transaction, I called him up and I said, “I got it done,” and he just went on and on saying thank you, god bless you, and it was a very special moment.

SB: How inspiring is it to see so many other women in leadership positions across the NFL?

AT: When women are hired, I’m often asked, “Does that excite you?” And the answer [I give] is, “What will really be exciting is when it’s no longer a novelty.” And that goes to gender, race, ethnicity, religion. When people are hired without regard to any other individuality, which has absolutely no bearing on whether they can do a job, that’s what will truly exciting.

SB: What advice would you give to women wanting to work in an NFL front office?

AT: Stop thinking about the fact that you’re a woman. Do your job, do everything you can to be the best you can be. And don’t think about your gender.

The second piece of advice, I think is the most important advice. Work hard. Work really, really hard. Hard work matters — it really matters. Work as hard as you can, and when you don’t think you can work any harder, find a way to work harder.

Third, it’s the best advice I’ve ever been given. My mom told me this from the time when I was a little kid, and she told it to me over, and over again: “To thine own self be true.”

Don’t try to be something you’re not. When I consider my best accomplishments have been when I’ve been true to myself. And what I consider my biggest stumbles or failures is when I try to be something I’m not.