When the Red Sox set out to find a successor for Dave Dombrowski last year, a primary goal of their search process was secrecy. They wanted deep dives into the backgrounds of candidates, and they wanted those depths scoured quietly.
They had just the person for the job on their staff: Samantha Barkowski.
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Never mind that a decade ago, she was a fan ambassador answering questions for ticket holders on game days. Now, at the age of 29, she’s an integral part of the Red Sox executive team.
Ownership gave Barkowski marching orders after Dombrowski was dismissed: Bring them troves of information on candidates who can run baseball operations. Personality traits, how they approach deals, interviews and media reports — anything she could find on how the candidates might fit into their system.
Barkowski’s investigative work was so clandestine that she often came in early or stayed late so she could print, read and organize binders on the candidates without having to hide the information from co-workers.
“It’s like having someone who works for the CIA in your own organization,” Red Sox president and CEO Sam Kennedy said with a laugh. “Because the intelligence she finds, digs up and presents to us in a very simple, digestible fashion is hugely valuable. I think one of the biggest skill sets in business and in baseball is taking a very complicated issue and trying to present it in a very simple and understandable way. She has that skill in spades.”
Barkowski grew up in Dorchester as the oldest of five kids whose mother, Katherine, is an assistant clerk magistrate for the Boston juvenile courts. She’s now the director of strategy and ventures at Fenway Sports Group, the parent company of the Sox that also owns properties like the Liverpool Football Club and Roush Fenway Racing.
But a career in the Fenway front offices was never really her goal.
When she applied for her first job with the Red Sox in 2010, she thought she was interviewing for a concessions gig.
That was sort of the hope, anyway. Selling popcorn at the ballpark over the summer can be decent money for an 18-year-old, and perhaps it could lead to a promotion to selling beer, where the real bucks are made.
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So 10 years later, when Barkowski was helping the Red Sox negotiate a new deal with concessions vendor Aramark, the irony was not lost on her.
Barkowski began, not as a concessions worker, but as a Fenway ambassador, a jack-of-all-trades position assigned to staff gameday booths throughout the concourse, assist the front office in various tasks, provide support at special events and offer assistance during pregame ceremonies. After working the summer of 2010 in that role, Barkowski found she really enjoyed the job, and managed to schedule her Harvard classes around her shifts at Fenway.
“It sounds silly now,” she said. “But I never thought of sports as a business or industry. You just kind of see the guys on the field and you know someone assembled that roster, but the whole business operation side of the team was never something I thought about. I really just needed the money and needed to work through school so I held onto the job but I really loved it.”
Over the next couple years, Barkowski got to see how a variety of departments within the Red Sox worked and started to contemplate that maybe she’d like to pursue a career on the business side. Her first big project was helping to coordinate Fenway’s 100th anniversary in 2012 and the following year she was part of a team that organized and executed the pregame ceremonies during the World Series — all while still in college.
“My experience being an ambassador, it’s just an incredible training ground for anyone interested in pursuing a career in sports or with a team,” she said.
“There’s the very exciting stuff with events and production but also there’s customer service booths day in and day out and in winning seasons it’s great but there were a couple losing seasons in there too.”
Another task she took on as an ambassador was filling in for any executive assistant in the front offices who may have called out sick. That’s how she connected with Ed Weiss, Fenway Sports Group’s general counsel and executive vice president of corporate strategy.
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Barkowski had been considering pursuing a law degree after graduation, so whenever she covered for Weiss’ assistant, it piqued her interest. She was considering her next steps when the executive assistant for the entire legal department left for another job, creating an opening.
“I really was maybe hungry for a bit of a bigger challenge once I graduated school,” she said. “At that point I would have been ambassador for almost five years, which is a pretty long tenure I think. Most people do it for a couple years right out of school and (Weiss) knew I was interested in legal.”
Barkowski graduated Harvard with a government degree in December 2014 and she began working as an executive assistant in Fenway Sport Group’s legal department in the spring. She didn’t have contract drafting experience, but Weiss had always been impressed by her work ethic and knew she’d be a good fit for the department even if she lacked traditional experience in the legal field.
“He knew I wanted to learn,” she said. “But that was probably the best place for me to gain an understanding of not just the Red Sox, but Fenway Sports Group’s broader portfolio, which allowed me to develop a much deeper more holistic understanding of the business generally, as well as how FSG is positioned in the broader sports media entertainment landscape. It’s really the only department that cuts across all of FSG’s portfolio so you get exposure, and it was a great position for someone innately curious.”
Shortly after she joined the legal team, two transactional attorneys on their staff left for other jobs, forcing Barkowski to take on more work in the uncharted territories of sponsorships and event contracts out of sheer necessity, before others were hired to fill the spots.
“Really that’s when she came on everybody’s radar screen because she stood out,” Red Sox president Sam Kennedy said. “One thing I think about when I think of Sam is her work ethic. It’s otherworldly.
“It’s hard to work in a legal department when you’re not a lawyer and you’re learning and right out of school. Just observing her work product and her contributions to the legal department, I just assumed she was out of law school or had been a lawyer before.”
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Her responsibilities with the legal team continued to grow as she helped Weiss more with the corporate strategy side, including deals with their major partners and operating agreements with rights holders like NESN. But she also got exposure to working with Rousch Fenway Racing and Liverpool. She was still considering pursuing a law degree, but didn’t have a strong desire to leave the Red Sox and FSG. Weiss also pointed out that she seemed to like the strategy of the business more than the actual legal work. Around that time, there was discussion of creating a separate corporate strategy team for FSG, so that Weiss and his staff could focus solely on legal matters. It made sense for Barkowski to make that shift.
So in March 2018, Barkowski joined Dave Beeston, the executive vice president and chief strategy officer of Fenway Sports Group Boston. Barkowski’s new role was as manager of research and intelligence, which encompassed a variety of wide-ranging tasks.
“We joke that Dave is kind of Sam Kennedy’s chief of staff and Dave and I are kind of the first line of defense when FSG is presented with opportunities. And the strategic aspect of that runs the gamut,” she said.
Beeston had known Barkowski while she was working for Weiss and figured she’d be a good fit.
“It was really easy to see the combination of intellectual curiosity combined with incredible work ethic,” Beeston said. “And then working in legal you learn discretion which is also part of the job a lot of time.”
They’ve coordinated everything from the Red Sox trip to London in the summer of 2019 to the organization’s COVID-19 task force, communicating to employees how the club would be operating amid the pandemic while also researching and assessing how other venues and businesses started to reopen. They’ve worked closely on the development and planning of the new music venue that’s being built behind center field at Fenway Park. They’ve monitored negotiations between major league and minor league baseball and what that means for the future of the Red Sox affiliates.
A big part of Barkowski’s role, which shifted this year to director of strategy and ventures, has been monitoring opportunities in the sports betting world and how that growing market will affect the Red Sox and FSG. There’s also an MLB strategy committee she and Beeston work on to research fan interest, engagement and the affordability of games.
One of the first big strategy projects she worked on last fall was evaluating concessionaire deals after Aramark’s contract with the Red Sox expired. The Sox opted to stay with Aramark, but the process brought her back to day one at Fenway, when she was just trying to get a summer job in concessions.
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After the Red Sox sifted through Barkowski’s binders of baseball operations candidates and then hired Chaim Bloom in October 2019, Kennedy gave Barkowski special recognition for her exhaustive research when the new chief baseball officer was introduced.
“It was definitely the coolest my brothers will ever think I am,” she laughed.
That same day, she found out she’d won an award as one of Sports Business Journal’s inaugural “New Voices under 30,” honoring young professionals shifting the sports business landscape. Beeston and Kennedy had nominated her. A few weeks later she went to New York City to accept her award.
It served as a reminder that for all the work she’s done for the club and Fenway Sports Group, she’s still not even 30.
“Sometimes I forgot she’s only (29), to be frank,” Beeston said. “She does have maturity in her work and work ethic that we all have a tremendous level of trust in her and the work she’s going to produce and knowing it’s going to be thorough and accurate and really, really good.”
Barkowski isn’t quite sure what the future holds, but knows she’s in a good spot with strong mentors and a lot of different avenues to pursue at Fenway Sports Group.
“The sky’s the limit for her,” Beeston said. “I hope we can keep her, and I hope I get to work with her a long time because she makes my life much easier. I would have no trouble seeing her as the president or CEO of a team if that’s the path she chooses or a media company or whatever endeavor she decides. The great thing about it is she’s (29) so she’s got lots of time to figure out what those next steps are.”
(Photo: Billie Weiss / Boston Red Sox)
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