Home / In House With... / IN-HOUSE WITH … Jennifer A. Flynn, Fenway Sports Management

IN-HOUSE WITH … Jennifer A. Flynn, Fenway Sports Management

Jennifer-FlynnIt’s probably safe to say that your office doesn’t bear much resemblance to Jennifer A. Flynn’s.

Flynn sat down with New England In-House at her Fenway Park offices in the midst of the Boston Red Sox’s championship run. The interview took place in a glassed-in conference room above the hallowed baseball yard’s third-base line. Tour groups walked by in a steady stream, Irish rock music blared as a technician put the stadium’s sound system through its p
aces, and concession smells permeated the air.

Flynn was promoted earlier this year to general counsel of Fenway Sports Management, or FSM, the marketing and sales arm of Fenway Sports Group, which is the entity that owns the Boston Red Sox, Liverpool Football Club, 50 percent of Roush Fenway Racing and New England Sports Network.

FSM aggressively explores global business opportunities that drive revenue growth for all the teams and brands in the family. Flynn also continues to serve as senior vice president and assistant general counsel to the Red Sox. She recently spoke with NEIH reporter Brandon Gee.


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Q. What’s it like to work in this environment?

A. I like it. From my office I can hear them announce the closing of Yawkey Way a couple hours before the games, and then you start hearing the vendors and start smelling sausage. I’ve been here 13 years. I think I am used to it in terms of living and breathing and working in Fenway. It definitely is unlike a normal corporate environment. … It does make it harder to concentrate on contracts and that sort of thing, but it does energize you.


Q. When did you know that you wanted to work in-house somewhere?

A. I think it was sports-related that I knew. I had sort of grown up in that environment. My grandfather had been the athletic director at Boston College for like 35 years and was the president of the NCAA. That was what was familiar to me, to work in that environment, so I had done a bunch of internships during and after law school with ESPN.com, Wolf Associates — which was a Boston sports representation firm years back — and the National Athletic Directors Association in Cleveland. I met a lot of lawyers who were not in firms, so it didn’t seem that unusual to me at the time to want to go in-house versus a firm, but it is certainly unusual, I think, to go directly in-house and not spend any time in a firm.


Q. How did you put yourself in a position to do that?

A. I kind of took a chance. I started here not in a legal position; I started here in a marketing position. And then the day after I started, the previous ownership announced that they were going to sell the team, so it was sort of like a yearlong wait-and-see period. The new ownership brought in a general counsel. She had worked at the Marlins, where [Red Sox owner] John Henry had been previously. She sort of took me under her wing and trained me, and then I moved over to the legal department. I sort of picked the place first, and then the skills I had led me to the positions that I’ve taken up since then.


Q. Would you recommend that sort of path to others?

A.  In the sports world, particularly, it’s important to get in. For sure it’s probably the safer route to head to a firm and then go from there to find an in-house job, but the sports world is a little quirky. The commissioner of the NFL started as an intern there. People in this industry need to get in however they can and then make themselves someone people rely on, need and trust. Once you prove yourself, that’s sort of how you’re going to move around. But I don’t think I’m typical, for sure.”


Q. What’s a normal day like?

A. I don’t think there’s a typical day. A lot of it is dependent on the time of year, particularly for the Red Sox. What is generally thought of as the baseball players’ off-season, that is really the busiest time for us because we’re preparing for the next season. … Anything that’s related to the operations at Fenway during a season, that’s when we’re doing that. January to April is very heavy for Red Sox activities. But at any time we could be doing a [FSM client] Lebron James endorsement deal or an arrangement for a special event at Fenway [from weddings to the NHL Winter Classic]. The RPM level here is really high in terms of operating the venue. … There’s always activity here, and there’s always a desire to make Fenway a destination for as large a group as possible.


Q. Is the diversity in what you do one of the

“pros” of the job?”

A.  It’s definitely a pro, particularly in terms of my career growth and career satisfaction. Over the 13 years I’ve been here, this organization has diversified and grown so much. … I would have never guessed I would have been involved in acquiring a European football club. When Fenway Sports Group was looking at The [Boston] Globe, I worked on the due diligence for that. It ended up just being a John Henry investment instead of a Fenway Sports Group investment, but it was interesting to learn about the newspaper industry. I was involved in the 50 percent acquisition of Roush [Racing]. … It does make it interesting, but it’s challenging and really pushes you to be a self-starter in terms of figuring things out.


Q. What’s the most outside-the-box idea you’ve had, and what was the result?

A. The biggest outside-the-box idea I had was to come here and take an entry-level, non-lawyer position. It turned out OK.


Q. What makes a good general counsel?

A. My boss would kill me if I didn’t say it’s knowing your business and knowing your company. You have to do whatever you can to keep up with industry news so that you’re not giving advice in a silo. I sit in our daily operations meetings, and I don’t necessarily have a lot to contribute, but it’s important to know what are the today and tomorrow issues. … It is important for me to know that when people come to me for advice and counsel. … At an individual level, it’s important to be reliable and trustworthy and to be able to give real practical advice rather than hypotheticals — and do it quickly, because in an organization like this, where things are always moving, people don’t have time for hypotheticals.


Q. What one word best describes your leadership style?

A. “Empowering.” I like to try to empower the people who are on our staff. That sort of requires people to be self-starters and have initiative to go. I try to give them examples of what to do and let them run with it.


Q. What professional goal have you yet to achieve?

A. I don’t know if I’ll ever really achieve it, but I’m always trying to be a better mentor to people here who work with me. I’ve been really lucky to have some really great mentors, and I want to be able to do the same. Sometimes you get caught up in the day-to-day and don’t always focus on that as much as I’d like to, so that’s a goal I’m always working toward.


Q. Any professional pet peeves?

A.  It’s real important, to be a good and effective general counsel, to give advice quickly and respond promptly. But there needs to be time to consider things and ruminate on things. So I don’t like when people come in and say they have a quick question and just want a quick answer, without having been able to give some thought to it if it’s necessary. My pet peeve is the quick questions, because they’re usually not quick answers.


Q. What would people be surprised to learn about you?

A. Since I don’t have a creative bone in my body, people would be surprised to learn that if I didn’t have this job, if I had to come back in another life, I’d really like to be a hotel interior designer. It would be so cool to travel around and pick out cool surroundings for people. But I could never do it because I’m not creative in the least.

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