Winter 2024 Issue

Power Plays

William & Mary alumnae tap varsity sports experience to build winning careers

By Tina Eshleman
Photo Illustrations By Sean McCabe

Winter 2024 Issue

William & Mary Alumnae Tap Varsity Sports Experience to Build Winning Careers

For women who aspire to high-level leadership roles, participation in sports provides a solid foundation. According to an EY report, 94% of women holding what are known as C-suite positions — chief executive officer, chief operating officer, chief financial officer — are former athletes, with 52% having played at a university level. Time spent on playing fields and courts fosters a strong work ethic, determination, a commitment to teamwork and a competitive spirit, the report states.

Athletics can help level the playing field for women in business environments. A United Nations report on women and gender equity notes that “women in sport leadership can shape attitudes toward women’s capabilities as leaders and decision-makers, especially in traditional male domains.”

To learn more about the connection between excelling at sports and leadership in the workplace, we asked several William & Mary alumnae athletes turned business and nonprofit executives to share their stories. Read more about alumnae making power moves in the business and nonprofit sectors at


At the Digital Pioneers Academy in Southeast Washington, D.C., school founder and CEO Mashea Ashton is wearing her usual Wednesday attire: a green-and-gold William & Mary sweatshirt. After all, Wednesday is College Day, and why wouldn’t the former Tribe soccer team captain represent her beloved alma mater?

Preparing students from low-income, working-class families to attend college and pursue careers in computer science is the mission behind the public charter school. Since opening in 2018 with 120 sixth graders, the academy has grown to encompass two campuses with 600 students in grades 6-11. Next year, its first seniors will graduate.

“I believe that every student rises to the level of your expectations,” Ashton says. “But data shows that for kids of color, particularly kids who live in the most under-resourced parts of the country, their educational outcomes are far below their potential. The big question I keep chasing is how to get more kids of color to achieve their highest potential by going to college and having successful careers.”

The question first came into focus when Ashton was teaching in Williamsburg while working toward her master’s degree in special education, after earning a bachelor’s degree in sociology and elementary education. One of her students was a fifth-grade boy whose behavior was getting him into trouble. A teacher on staff at the school told Ashton not to worry about him: “He’s just going to wind up in jail like his father.”

“I remember thinking, ‘Oh, gosh, this can’t be true. There must be something else out there for him,’” Ashton says.

The story of how she came to attend William & Mary — and discover her life’s mission — begins with athletics. As soon as Mashea and her twin sister, Michele Mason ’96, entered kindergarten, their mother, Brenda Mason, started making plans for the girls to go to college. Neither she nor her husband, who served in the military, had a college degree, but it was her dream to see her daughters pursue higher education.

While volunteering with the Willingboro, New Jersey, school system, Mrs. Mason told one of the teachers that her daughters needed to receive scholarships and she thought excelling at basketball might be the best way for them to accomplish that goal.

“This teacher told my mom, ‘Don’t put them in basketball, put them in soccer,’” Ashton says. “I think the idea was that there aren’t many Black girls who play soccer. If they’re really good, they will stand out and they’ll have more opportunities to get scholarships.”

So the twins started playing club soccer at age 5, and they loved it. About a decade later, their team, the Willingboro Strikers, became national champions for the under 16 age group. William & Mary was not on their radar while growing up in southern New Jersey, but they met John Daly, then the W&M women’s head soccer coach, at a Women and Girls in Soccer tournament, and he told their mother the girls should think about going to William & Mary. His suggestion was reinforced when they heard about W&M’s reputation for both high-level academics and athletics from one of their club soccer coaches whose child had attended the university.

“We said, ‘It’s our dream school. That’s where we want to go,’” Ashton says. “It’s the only school we applied to.”

She credits her experience as an athlete with honing her leadership skills and teaching her how to overcome disappointments and setbacks. She recalls that after starting most games as a freshman, she lost her spot in the lineup when a new player came in the next year.

“Why is a freshman taking a starting position?” Ashton asked Daly. He told her that he made the decision based on his assessment of how the players’ skills would contribute to the team’s success, and encouraged her to keep improving as an athlete.

“Competition pushed me to work harder,” she says. “By my junior year, I was starting. Senior year, I was picked to be captain. A big part of that was input from the coach. He reinforced that if you work hard, good things will happen.”

As she began her career in education, she carried with her the competitive spirit from the soccer team, along with lessons of resilience.

“I understood working hard and getting results from an athletics perspective, but the same perspective can apply to anything,” she says. “If you set your mind to a big goal, you work hard, you put in the effort and you believe all failure or difficulty is just feedback, you can achieve anything.”

After starting out as a classroom teacher, Ashton soon moved into leadership roles. At age 26, she became a founding member of the Black Alliance for Education Options, a nonprofit that advocated for increased choices for low-income and working-class families. She served on the board with Cory Booker, a U.S. senator who was then the mayor of Newark, New Jersey. Booker later recruited her as CEO for a $50 million fund that was set aside for charter schools in Newark. Ashton also has served as executive director for charter schools in the New York City Department of Education and as national director of recruitment for the Knowledge Is Power Program.

“I didn’t pick charter schools,” she says. “I picked leadership roles based on how to have an impact to serve kids.”

The idea of charter schools resonated with her in part because of personal experience. Her parents had moved Mashea and Michele out of their zoned public school when they were going to be held back to repeat kindergarten. They transferred to a private Catholic school, where they received additional academic support and were able to catch up with their peers.

“I believe families deserve as many high-quality choices as possible,” she says.

Working with charter schools enabled Mashea to apply an entrepreneurial approach to education, eventually leading to the founding of Digital Pioneers Academy (DPA). About 10 years ago, she and her husband, Kendrick Ashton ’98, moved from New York City to the Washington, D.C., area, where his family has lived for generations, as he was making plans to launch The St. James sports complex with friend and business partner Craig Dixon ’97, J.D. ’00.

Mashea has reconnected with her alma mater as a current W&M Foundation trustee, and former For the Bold D.C. Regional Campaign board member and W&M Alumni Association board member.

Originally, she wanted to open a middle school that would help put students on a path toward college and careers. Then she read reports saying demand for people trained in computer science was expected to far outpace the supply, and that gave her the inspiration for the academy.

“I said, ‘Let’s figure out how to close this gap,’” Ashton says. “We want our scholars to be part of creating in the digital economy.”

Taking the school from concept to opening was a major task, and challenges continue. After four of the academy’s students died from gun violence in incidents outside of school during the last academic year, Ashton began to rethink how DPA operates.

“What I’m realizing is that we can’t achieve our mission for all of these kids to go off to four-year colleges and universities and thrive in 21st-century careers unless we are also thoughtful about addressing youth violence and gun violence in D.C.,” she says.

Part of the school’s response was to launch a football team, which finished its first season this past fall. Additional sports are also being added: girls and boys volleyball, basketball and soccer. These activities give students something to do in the after-school hours and provide a way to engage families and build a sense of community.

Meanwhile, Ashton keeps her team focused on Digital Pioneers Academy’s mission, often drawing on her athletics experience.

“We have a 15-minute huddle at the start of every day with the whole staff. It’s the moment our team loves the most,” she says. “We talk about the play for the day and then we go try to win. Our mindset is we have to go 1-0 every single day. We’re not trying to win the championship in one day. We’re taking it one day at a time.”


Before launching into a conversation about the role athletics played in her life and career, Molly Ashby wants to make it clear that she doesn’t see participation in sports as the only path to professional success.

“Aspects of athletics and athletic competition can be accomplished in other pursuits,” says the founder, CEO and chair of private equity firm Solera Capital. Still, “there are several very clear and contributive aspects of competitive athletics that lend themselves to success later in life.”

Ashby grew up playing a variety of sports in Southern California and became an accomplished tennis player, eventually landing a spot on the team at University of California, Santa Barbara. She wanted the experience of playing for a highly competitive West Coast tennis program, but her plan was always to graduate with a degree from William & Mary, her father’s alma mater, so she transferred after her first year at UCSB.

Lt. Cmdr. Donald Roberts Ashby Sr. ’51, P ’81 had been an instructor in the U.S. Navy’s fighter pilot school in Pensacola, Florida, where Molly was born, before the Ashbys moved to San Diego. From there, he served with a fighter squadron aboard the aircraft carrier USS Kitty Hawk. Tragedy struck in early 1967 when the fighter plane Donald Ashby was flying crashed in the Gulf of Tonkin during the Vietnam War, killing him and a fellow crew member. Molly was just 7 years old at the time.

“It meant so much to me to be able to go to William & Mary, where he had been,” she says.

There, her priority shifted from tennis to academics.

“I played a bit on the William & Mary team under Millie West HON ’91, L.H.D. ’17 — who was an extremely impressive and formidable woman — but not for that long, because it was the right thing for me to focus more on the rich intellectual and inspiring academic environment of William & Mary, which was not something I had particularly known before,” she says.

As a star tennis player in high school and then a member of the Division I UCSB team, Ashby says her grades had been secondary to her athletic success. At William & Mary, she became part of the Phi Beta Kappa honor society. Through interdisciplinary studies, she combined history, government and political science to form an unofficial international relations major.

After graduating, she earned a master’s degree in African studies at Georgetown University’s Walsh School of Foreign Service. As part of that program, she completed an internship in Mali, West Africa, where she studied food policy. While there, she met foreign service officers who advised her to start her career in the private sector before going into public service.

Taking their advice, she interviewed with JPMorgan Chase & Co. and began working at the global financial services firm, with the intention of leaving after a time for foreign service.

“And then I just kept getting so many good opportunities and I was so engaged and so challenged and learning, and I thought I can probably make a bigger difference from here,” she says.

At JPMorgan, she moved up from investor to investment strategist and then chief operating officer at JPMorgan Private Equity. One of her notable deals involved orchestrating a $5.1 billion leveraged buyout of Hospital Corp. of America (HCA), as reported by The Wall Street Journal. With transactions of such size, scope and complexity, the people involved need to be moving in the same direction, just as they would on a sports team, she says.

“If the team doesn’t work together and is always in little battles with itself, you’re going to lose,” Ashby says. “Your team needs to be united. They need to have a set of values. They need to believe in their leader.”

Recalling her time at JPMorgan, she adds, “I worked for an outstanding person. He and his superior were not just strong leaders, but men who cared as much about my development and success as that of our business. I have tried to model myself on what I experienced.”

In addition to teamwork, athletics cultivates mental and physical toughness, she says.

“What I have found is that athletics teaches you how to win and it teaches you how to lose, and it teaches you to get up the next day and go right back at it,” Ashby says.

Women tend to take setbacks particularly hard, she says, adding, “I was exactly that way. I had to learn over time to just look straight ahead and say, ‘Understand what went wrong. Think about it. But don’t let it get to you.’ And the same is very true in sports.”

When Ashby’s older daughter, Frances, was born, she was chief investment strategist for the JPMorgan Private Equity Group. As a new mother, Ashby began to reconsider the amount of time she was devoting to work.

“We had a large amount of capital invested around the world,” she says. “At 10 p.m., Asia would kick in and then Europe at 5 a.m., then the U.S. and Latin America. It was a very demanding job and we had a fantastic portfolio, but I lived and sweated that every hour of every day.”

With Solera, founded in 1999, she was able to shape her own company from scratch.

“I always had this vision of a firm that should exist in our industry and it’s one that would have a significant commitment to diversity and bring people into private equity who weren’t necessarily always invited in,” she says.

Even though she attracted a groundswell of support based on her vision and her experience at JPMorgan, persuading investors to commit to a brand-new fund was an uphill climb.

“There was some hard slogging. There were obviously positives. There were disappointments, and then we got it done. We raised the fund and we were off to the races,” Ashby says.

One of the firm’s early investments is also one of its best-known successes: organic snack foods enterprise Annie’s Inc. At the time, Annie’s mac-and-cheese was sold mostly in natural food markets.

“We look at a sector that we think is going to be high-growth and super attractive for at least 10 years,” Ashby says. “One of our rule sets for what we pick is that we have to believe the growth in the sector we pick is nonreversible and it shouldn’t be a fad.”

In the case of Annie’s, her assessment of its potential proved to be on target. After Solera gained a controlling interest in the company, Annie’s products expanded to mainstream grocery-store shelves across the country. Solera’s $81 million investment in Annie’s grew to hundreds of millions, The Wall Street Journal reported. The company’s stock rose from $19 per share at its initial public offering to $46 per share when General Mills bought it for $820 million in 2014.

What does the future hold for Ashby? She still thinks about returning to Mali one day. Maybe she’ll take up a career in foreign service after all.

“I developed a tremendous affinity for the people of West Africa,” Ashby says. “I would love to go back at some point, and more importantly, I’d love to figure out a way to make a difference there.”


As a 14-year-old starting high school, Katy Neumer observed her mother working three jobs to take care of her and her twin sister after her parents divorced. Already an accomplished basketball player, Neumer set an ambitious goal: “I told myself that I was either going to get an academic scholarship or an athletic scholarship, and I spent my high school years very focused on those two objectives.”

Her efforts paid off when she secured a full scholarship to play basketball at William & Mary.

“It is probably one of the proudest things in my life that I’ve ever done, just because I knew it helped my mom out so much, and it helped our family out,” Neumer says.

She became class valedictorian at her high school in Winter Park, Florida, where she also set a record as leading basketball scorer for both men and women — a record that still holds for women, although current NBA player Austin Rivers surpassed it more than a decade ago to set a new record for men.

The practice of setting a goal and working toward her objectives developed into a pattern as Neumer attended William & Mary, where she became captain of the basketball team, and then as she began her career in the finance industry. In her current role as founding member and managing director at J. Wood Capital Advisors in San Francisco, she advises public companies on how to raise capital in a more efficient way.

“Of the women I interact with who are CEOs or CFOs, probably eight times out of 10, there is some sort of athletics experience in their background,” she says. “I think that that makes sense because they have to engage with their team and engage with investors. They have to understand skill sets to put people in places where they’re going to succeed.”

One of the C-suite women Neumer advised was Kelly MacDonald, now chief financial officer at Dynavax Technologies, who had played softball as a college student. The two developed a personal relationship and they married in 2022.

Sports training correlates with achieving business objectives, Neumer says, noting that if athletes fall short of a goal, they don’t throw their hands up and walk away. “They go back to the drawing board and figure out the next step.”

Playing on a Divison I NCAA basketball team was humbling at first for Neumer, who was used to being the star player at her high school.

“At William & Mary, every single one of my teammates had my exact same resume, if not better,” she says. “I had to figure out where I fit.”

Realizing she was no longer the player scoring the most points, Neumer discovered other ways in which she could help the team succeed.

“I don’t know if you appreciate the true value of teamwork when you’re the head of the snake,” she says. “I think you learn it the best when you’re at the end of the bench.” As an example, “during practice, I would guard our best player and make it absolute torture for them, so that they were prepared to go score 20 points against the next team.”

She persevered through a dismal season during her sophomore year, when injuries kept key players off the court. The next year, after the injured players returned, the team tied for biggest turnaround in the NCAA, and by her senior year, Neumer was part of the starting lineup. She was also selected as a co-captain, something she attributes to putting the good of the team first.

“Being a captain is about leading the culture of the team, whether that’s in sports or outside of sports,” she says. “How are you setting the right example? It’s having a never-give-up mentality.”

After graduating with a business degree from William & Mary, Neumer considered applying to law school, but decided to explore the world of finance on Wall Street when she was offered a job as an analyst with Bear Stearns Cos., now part of JPMorgan Chase & Co. While working in private banking at JPMorgan, she started to explore investment banking by seeking out contacts in that area of the company.

“Through networking, I learned about what the roles were in the investment bank, and when there was a position open I was one of the first people that they called,” she says.

Having secured an investment banking position and moved to San Francisco, Neumer faced a steep learning curve.

“That circles back to my early experience of being an athlete at William & Mary, where all of a sudden I’m a fish out of water and I’m not as good as I thought I was,” she says.

Like she had done as a basketball player, Neumer looked for ways to add value to her team. She credits Jason Wood, then head of equity-linked capital markets at JPMorgan, as one of the teammates who helped her learn the ropes.

“They saw something in me that I didn’t see at the time when I had a lot of self-doubt,” she says. “Thankfully, I turned that corner.”

When Wood decided to leave the firm and start his own company in 2013, he asked Neumer to join him, citing her skill at relating to clients. The two of them ran the business out of Wood’s attic for the first couple of years and have since expanded the team to 15 people. Since its founding, J. Wood Capital has advised on a total of $140 billion in capital markets activity representing over 160 clients across the United States, Neumer says. Those include companies such as Cracker Barrel, Domino’s Pizza, Groupon, Intel, Live Nation, Peloton, Planet Fitness, Slack, Snapchat and WWE.

Neumer maintains connections to William & Mary in part by serving as a board member for the Boehly Center for Excellence in Finance at the Raymond A. Mason School of Business, where she participated as a keynote speaker in the 2023 Women’s Stock Pitch and Leadership Summit.

In her message to students, Neumer advised them to be open to new opportunities and not to feel pressure to have their career fully mapped out at graduation.

“What I do now is such a highly nuanced thing, where I advise public companies on how to structure and execute on convertible debt securities,” she says. “If you would have asked me if I wanted to do that as a 22-year-old kid, I would have had no clue what you were talking about. What I told them is it’s OK to make decisions along the way.”


As a Tribe soccer player, Jen Mackesy was known for leading her team in assists — a skill she believes is undervalued by many players and their parents.

“I would say my strongest attribute when playing was my ability to read the field,” she says. “I loved the idea of creating opportunities for my teammates who were probably better at finishing the play.”

During her first year, the team ended up in the top five in the country. Teammates included Jill Ellis ’88, L.H.D. ’16, P ’27, a U.S. national women’s team soccer legend who is president of the San Diego Wave FC, and Kathy Carter ’91, a senior advisor and former CEO of LA28, the summer 2028 Olympic and Paralympic games, along with current W&M women’s soccer head coach Julie Cunningham Shackford ’88, P ’23, Megan McCarthy ’88 and Nancy Reinisch O’Toole ’88, P ’23. Associate Tribe head coach Marsha Fishburne Lycan ’87 also played soccer as a student.

Learning to assess a situation, identify others’ skills and rely on teammates served Mackesy well on the soccer field, where she made four appearances in the NCAA Championships while at William & Mary. Those skills, combined with her academic background as a marketing major, helped her rise through the ranks in the retail and fashion industry to become a vice president at Lord & Taylor, overseeing the buying office.

“The buying-office job involved multitasking and it was analytical, creative and managerial,” she says. “High-level athletics prepared me to be able to do all those things and do them well. It gave me the confidence to be in a room with the CEO and senior-level executives and sell them on an idea.”

Today, Mackesy is combining her athletics experience, marketing expertise and managerial acumen as part owner of NJ/NY Gotham FC, a National Women’s Soccer League (NWSL) team based in New Jersey. In addition to NJ/NY Gotham, Jen and her husband, D. Scott Mackesy ’91, are part of the ownership group of Chelsea FC in London with Todd Boehly ’96.

Mackesy’s path to soccer team ownership began a couple of years ago when Boehly invited her to join him in negotiations to purchase a controlling interest in the NWSL's Washington Spirit team. In the early 2000s, she had stepped away from her retail career to focus on nonprofit board service while raising her two young sons, both of whom also became college athletes. As a board member for U.S. Squash, she helped guide the organization as it built its first national training center in Philadelphia and successfully pushed to include the sport in the LA28 Olympics.

Boehly’s offer came at a time when she was considering her next career step.

“At first I wasn’t sure about it, but I started reconnecting with some of my former teammates as part of my due diligence for whether this was something I was prepared to take on,” she says. “What it made me realize is this is exactly what I want to be doing for the next 20 years.”

Mackesy was disappointed when the Washington Spirit purchase fell through, but she began looking for other sports ownership opportunities, leading her to NJ/NY Gotham.

“By luck, a neighbor of mine, also a former Division I college soccer player, happened to know one of the operating owners at NJ/NY Gotham, and they put us in touch and I was fortunate to become one of the minority co-owners,” she says. “I realized this would be a way for me to give back and help promote something that is so important to me, and that allowed me to have the opportunities that I did. I was also confident it would be a good business opportunity.”

Since Mackesy became involved with Gotham in mid-2022, she has played a role in hiring a new coaching staff and building a new practice facility and office space for the team.

“Even though the NWSL has been in existence for 12 years now, these clubs still feel very much like startup businesses,” she says, noting that the cost to acquire a team has risen from $2 million to over $50 million during the past several years.

“There’s been exponential growth in value, but also exponential growth in terms of the workload and the resources needed to run these clubs at the level they need to be run,” she says. “I was able to get in at a very exciting time, but a very busy time.”

After finishing last in the NWSL in 2022, the Gotham team claimed its first championship this past fall. Watching the game with Mackesy in San Diego on Nov. 11, 2023, were former teammates Ellis and Carter.

Mackesy has remained involved with William & Mary Athletics through her work on the W&M Foundation Board of Trustees. She was chair of the board’s athletics subcommittee during most of the recently concluded, successful All In campaign for W&M Athletics, and she served as an honorary campaign co-chair, along with Scott Mackesy, Todd Boehly and Katie Garrett Boehly ’95. One of campaign’s objectives was to provide equitable participation opportunities, scholarship support and better access to top-notch facilities for women athletes.

Today, Mackesy continues her nonprofit leadership, which includes a longtime association with Graham Windham, a New York City-based organization that supports the needs of children and families, and more recently William & Mary’s Global Research Institute Advisory Board.

In her role at GRI, she sees an opportunity for athletics to help improve the lives of people in developing countries. When she traveled to the FIFA Women’s World Cup in Australia last year, she observed striking inequities between teams from around the world in terms of training, compensation and travel.

“I would love to be able to play a larger role in trying to help balance those inequities, whether they are gender-related or socioeconomic,” she says. “I’ve always said that I see athletics as a way to level the playing field. I think that athletics and sport are a way to address the social issues that are really important to me and are things that I have been involved in as part of my nonprofit work, and I’m excited to find ways to do that.”