Now vice president of HNTB in Boston and a member of the design firm’s national tolling group, O’Meara proudly ticks off prominent transportation and infrastructure sector jobs now held by women, including top positions in state transportation agencies, the federal government and major companies. “You didn’t have that even 10 years ago,” she says.

Featured in a 2015 book about women trailblazers in transportation—“Boots on the Ground, Flats in the Boardroom: Transportation Women Tell Their Stories”—O’Meara notes that while progress was slow at first, the momentum propelling women into the field has been growing in recent years. “The best decisions get made if your table is mixed,” she says. “You don’t get your best decisions if it’s all women, or all men. You need to have the mix.”

For her role in pioneering women in transportation management, and for other accomplishments over a long, ongoing, career, ENR New England has chosen Mary Jane O’Meara to receive its 2021 Legacy Award.

Start in Politics

O’Meara’s first big break came via politics, not transportation. Having spent several years at home raising two daughters, she sought a way to get back into the workforce and onto the career ladder. It was 1982, and her husband, Gregory, had heard the campaign manager for the late Rep. Joseph Moakley, a Democrat whose district included South Boston, needed help. O’Meara landed a job running the campaign manager’s office.

Her work with Moakley led in 1983 to a job with the Massachusetts Bay Transportation Authority. The following year, O’Meara, who had interrupted her  studies to raise her children, earned a degree in planning from the University of Massachusetts. “I love planning,” she says. “You have to plan before you can move ahead with anything. It’s the way my mind works, and it comes in handy for this type of work.”

O’Meara’s first transportation job was to help plan expanded commuter rail service to Fitchburg, an old industrial city some 50 miles north Boston. From there, she moved into the transportation agency’s construction planning unit and worked on the Orange Line. A  high point came when O’Meara was put in charge of overseeing $100,000 in federal funding that MBTA obtained in 1986 to erect a statue to noted Black civil rights leader A. Philip Randolph in Back Bay Station, one of Boston’s busiest subway and rail hubs. Randolph unionized Black railroad sleeping car porters in the 1920s. “It was fun,” O’Meara says. “I had not done anything in the arts.”

From Planning to Tolls

O’Meara’s next career move came in a field she had never contemplated. She was approached by a woman colleague at the Massachusetts Port Authority who interested her in taking over as operations manager for the Maurice J. Tobin Bridge, a cantilevered truss toll bridge connecting Boston to commuters from the North Shore that opened in 1950.

O’Meara decided to take the leap, despite what she jokingly described as a harrowing first day on the job. Walking into the cafeteria to greet toll workers on break, O’Meara had just spotted the “wet floor” sign when she went flying. “As I looked, one shoe went one way, my pocketbook went another,” she recalled.

O’Meara also got acquainted with her office, tucked under the 254-ft-high bridge, nine stories up. “It was like working in a shake and bake,” O’Meara says. “You knew when a 16-wheeler went over.” Later, getting into the elevator, the cab stopped moving between floors. Her two assistants rushed to pry the door open with a broken broom handle and get her down from the elevator, which had stalled 3 feet up. “It’ a miracle I went back after my first day—it couldn’t go anywhere but up,” she says.

O’Meara not only came back, but was promoted to director of the Tobin Bridge two years later. As head of the bridge and its tolls, she oversaw a 100-person team also tucked into a box underneath the bridge, from engineers to toll collectors, auditors, mechanics, electricians and maintenance personnel. O’Meara handled everything except for capital projects, but she was still responsible for keeping the bridge operating.

But there was also construction, including a redecking of the bridge’s upper and lower sections done in phases between 1991 and 1995, an expansion of the deck and toll plaza and other structural repairs. Once O’Meara got an ominous sounding call in the middle of the night. “Something has shifted, you had better get in here,” she was told. The bridge had indeed shifted, but under O’Meara’s direction, it was ready to be reopened in time for rush hour, with staff working wonders using a steel plate.

There were sometimes political issues to deal with as well since the bridge spanned Boston and Chelsea, with mayors and other officials ready to unload their frustration should a traffic accident on the bridge make a mess of rush hour. “It was a bigger operation than I ever envisioned,” O’Meara says. “It opened up so many different doors.” Snowstorms meant 24-hour duty. “If there was a bad storm, I would go in and bring a bag—sometimes I wouldn’t get home for a couple of days,” she says.

She also contended with the bridge’s attraction as a local spot for suicides, with more than one middle-of-the-night call after someone jumped off the deck into the Mystic River below. Among the more infamous jumpers was Charles Stuart, after shooting his pregnant wife in early 1990 and blaming the murder on a Black man. “I was on my way to work when that happened—it had just happened when I got called in,” says O’Meara. “Every media outlet was there—they were just stopping on the bridge.”

During her two-decade-long stint running the Tobin, O’Meara also became heavily involved in bridge, transportation and toll industry organizations, eventually becoming president of the International Bridge, Tunnel & Turnpike Association, while also serving as a board member and on numerous committees.

A longtime member of the Women’s Transportation Seminar Inc., O’Meara is a past president of the Boston chapter and spent time on the chapter board. She also has served as WTS International president.

O’Meara launched the New England Toll Association to help regional authorities unify electronic toll collection systems and then chaired the group for two decades. She recently was cited for lifetime achievement by the American Road & Transportation Builders Association, which noted her “40-plus-year commitment to the transportation industry, including the advancement of female leadership.”

Says O’Meara: “I like fairness—I want everything to be fair for everyone. Also, if you join an association, you get more out of it by getting involved. Hopefully, you can help the next generation.”

Along with playing a major industry leadership role, O’Meara also put countless hours into mentoring younger colleagues. “I never say no to anyone who asks me for my help,” she says. Overall, engineers “tend to be more introverted—if they reach out, you need to reach back and help them find their voices.”

Some of her mentoring involves helping talented younger women gain “the confidence to do the job they want to do,” she says. That can also involve “encouraging them and working with them through issues and problems they may be having.” Helping someone find his or her voice—and ask for what they want—is key, she says, even if it doesn’t produce immediate results. “The next time the supervisor is going to remember who you are,” she notes. Over the years, O’Meara says she has kept a close eye on the careers of her mentees. “I feel like a mother,” she says.

Last  year, the Boston WTS chapter renamed a scholarship in O’Meara’s name, a $4,000 graduate award for higher education in the transportation field eligible to women members who are full-time employees.

Christine Keville, president and CEO of Keville Enterprises Inc., got to know O’Meara from working together in industry organizations. Keville calls her “one of my most esteemed mentors.” She adds that “one piece of advice that Mary Jane has always instilled in me is the importance of mentoring and giving back to industry.”

Keville, ENR New England’s Legacy Award winner last year, also praises O’Meara’s leadership skills, calling them “one of her most notable traits.” According to Keville, O’Meara “recognizes the value of others and is very much a team player. She doesn’t care who gets the credit as long as the job gets done.”

Private Sector

After decades in public service, O’Meara moved into the private sector in 2011, going to work for HNTB. The firm’s national tolling group, in which she is a part,  provides specialized consulting in tolling system financial, engineering feasibility and design aspects as well as in priced managed lanes and all-electronic toll conversion, interoperability and operation.

She says that she came to the job with a long track record of working with teams and a Rolodex of tolling sector contacts. Her focus is business development, with the ability to add to an RFP response the insight of what public sector decision makers may be thinking or seeking in a particular contract or project. “I am able to connect people with people,” O’Meara says. “I am very good at saying ‘when I was in the public sector, this is what I wanted.’” Although not an engineer, O’Meara says she was immediately taken “with the smartness of the group” at HNTB.

O’Meara brought to the private sector her dedication to mentoring employees, who seek “her out for guidance and counsel on what they should do in thinking about their career and engaging in leadership,” says Phil Brake, president of HNTB’s Northeast division.Brake credits O’Meara with giving him and other executives at the company a better understanding of the concerns and ambitions of all employees, with a keen understanding of where they are coming from. “She has really improved our working environment,” Brake says. “Mary Jane is a down-to-earth person who people go to and trust and feel as though she is really interested, as a person and as a professional, in the development of their career.”