Lawdragon: Q&A with Jane Sullivan Roberts

In this “Legal Consultant Limelight” feature, Jane Sullivan Roberts takes Lawdragon CEO Katrina Dewey on a global journey from the stickball games of her Bronx childhood to her Big Law partnership to her current role as Managing Partner of Macrae’s thriving D.C. office.

[This article was originally published by Lawdragon here.]

A stick slaps against the ball, and kids roar in excitement as the leaves make their way toward rust and crimson on Holland Avenue in the Bronx.

“The sewer was home base. The tire on a parked car was first base. Another sewer was second base and another tire was third base,” recalls Jane Sullivan Roberts of her childhood and the joys of playing stickball, volleyball, boxball and a constant hubbub out in the streets.

“We had so many kids on our street that we could field two teams without crossing over to the next street,” she says of her Irish-Italian neighborhood. “We were not segregated into boys’ teams and girls’ teams; they were integrated and the girls played just as hard as the boys did. At that age, there wasn't a big difference in height and size so we were as good as they were.”

The rules were simple. So was life. Family, church, competition. Fierce dreams of working hard and gaining a better life.

Roberts has a rare enthusiasm for grabbing life’s experiences and always aiming to improve. Her mother taught her to make the bed when she stayed in a hotel as a treat for the maid. “We were taught to leave a place better than we found it,” she says.

And in her life, she is doing just that, personally and professionally. She is among the very best legal recruiters in the country and the managing partner of Macrae in Washington, D.C., where she helps lawyers assess their careers and guide them toward new vistas.

Her verve and interest in learning and experiencing all life had to offer led her to study mathematics, then law, and live in Australia, West Virginia, and Minneapolis before settling in Washington, D.C. She was a systems engineer at Bell Labs before going to law school, and a partner at Pillsbury practicing technology law before switching gears and developing a new approach to recruiting and professional development. She thought there was room for improvement.

Her move to professional recruiting at Major Lindsey & Africa in 2007 was inspired by her husband’s new job. John G. Roberts Jr., a longtime Supreme Court advocate from Hogan & Hartson, had been appointed to the District of Columbia Court of Appeals in 2003. In 2005, U.S. Supreme Court Chief Justice William Rehnquist died and Roberts was confirmed as his successor.

While she could have stayed at Pillsbury, she was concerned about the appearance of conflicts and heard out a friend who suggested she consider recruiting.

“There are many paths to a good life,” she says from her summer house – which became a home during Covid. It’s on an island in Maine, where she plans to paddleboard and pick up some freshly raked blueberries later in the day. “People are probably not going to be in the same job for 40 years. There are so many interesting things to do if you’re open to change and opportunity.”

Lawdragon: Can you tell me please how you came to be a lawyer?

JSR: We had law as a background in my family; my maternal grandfather was the longest-serving law clerk in the history of Ireland, for 61 years. One of my aunts, my mother’s sister, who came to Connecticut, had worked with him in the solicitor’s office.

While my maternal grandfather was not a solicitor, he essentially acted as one, because he was both very smart and down to earth and so all the farmers loved to do their transactions with him. At Christmas, they would bring him a goose or ham to thank him for his work. And one of my granduncles in Ireland was a member of the IRA and fought for Ireland's independence from England in the 1920’s. After the war, he became the clerk of a local court, and he served in that position for decades.

LD: As a child, you spent some summers in Ireland. What were your impressions of your relatives who worked in the law?

JSR: As a kid, I thought of my grandfather as smart, careful, considerate, and admirable in those ways. My granduncle had an even more colorful life. As a courier for the IRA, he transported lots of money in a mere briefcase. His modus operandi was to act totally nonchalant, throw the briefcase onto the bus, climb onto the bus, and carry it to the next city. He had to be really cool under pressure.

He did eventually get caught and served time in a prison in Northern Ireland. He went on hunger strike where he met his soon-to-be bride, because she was teaching the Irish language to inmates. So they were both patriots.

My mother, on the other hand, had worked in a hospital and I was very interested in that as well. When I started at the College of the Holy Cross, I was a pre-med and a math major.

LD: What happened to Jane Sullivan, M.D.?

JSR: While I liked the science classes very much, I hated the laboratories – especially because they were in the late afternoon overlooking the tennis courts and I would have much preferred to be playing tennis.

Even though I worked for a couple of summers in the hospital I dropped pre-med and became a math major. I loved math and I was really good at math. I also loved history, and I was good at that but I thought, “I can teach myself history. I need a professor to help me with math.”

LD: So when you graduated college, you moved to Australia! That’s so interesting. How did it happen?

JSR: I got a Rotary International Fellowship to study overseas, and I took it in Australia at the University of Melbourne. I thought, “Well, math is the same all over the world, so why study math in Australia?” I preferred to study something that would reflect Australia’s culture. So I studied education and the current thinking in Australian education.

It's interesting because they were going through massive post World War II immigration and it was impacting neighborhoods and schools, and we had been through similar waves earlier in the U.S. It was interesting to compare what the United States did in the 1880s, 1920s, etc., to what Australia was doing in the 1970s.

I gave talks at Rotary lunches on New York immigration patterns, which they could compare to what was going on in the city of Melbourne. I stayed for a second year, teaching math, science and religion in an all-girls Catholic high school, and then I stayed a third year, just studying math.

Then my mother said, “Well, when are you coming home?”

LD: Mom for the win. What came next?

 JSR: I applied to both math graduate school and law school. Brown University gave me a full scholarship to study applied math, while I basically would have had to pay for law school myself. So I said, “Let me try applied math and see if I like it. It doesn’t cost me anything except time, and I’ve got time.” After my master’s degree, I considered a PhD program but asked, “Do I really want to do that?” So I said, “Let’s see what math in the real world is like.”

LD: And what did you find?

JSR: I was a systems engineer at Bell Laboratories, which was quite interesting. I worked on an aspect of the caller ID project, which was an enormous undertaking at the time.

LD: Can I presume you were one of the rare women in the field at that point?

JSR: I wasn’t the first woman at Bell Labs, but it was the early days of women working there. I felt comfortable working alongside men and that we were treated just the same. Maybe it comes from playing in the streets as a child, growing up with boys and girls on the same teams. Or just that I had experienced such a mix of settings by the time I got to Bell that I didn’t think much about it.

My Catholic high school in the Bronx was all girls and at Holy Cross I was in the first class that included women. Holy Cross was incredibly welcoming to the first class of women. We comprised a third of the class but close to half of the students in honors math, which I think is pretty interesting. Brown began admitting women several years before I started, but I was in the first wave of women in the applied math PhD program – there were just a few of us.

Then, at Bell Labs, most of my colleagues were men but it was all about the work, what we were capable of, not what gender we were. There were some remarkable women there, like Shirley Jackson, a scientist a decade or so older than me who had been the first Black woman to receive a PhD from M.I.T. and went on to become the first Black and first female president of Rensselaer Polytechnic University.

LD: And then you went to Georgetown Law. What was that transition like?

JSR: One, I was excited to be dealing more with the social and legal fabric of our country, rather than the technical, scientific aspects. Legal cases are kind of like stories, and reading stories was refreshing after working with math problems for years. I was also excited to be in law school and at the prospect of becoming a lawyer.

LD: Was that your first time living in Washington, D.C.?

JSR: I had done an internship on Capitol Hill for my Congressman for a year, but I was still relatively new to Washington. This was the early 1980s. The downtown area had been torn apart by the riots of 1968, and had not yet recovered. It was so quiet at night, unlike the nightlife and neighborhood life of New York.

I had a little Volkswagen bug and I remember driving around wondering, “Where’s downtown? Where do you go shopping here? Where are the bars?”

I was studying hard, though, and my social life was fellow students and the parties or dinners they might have. It’s not that I really missed the hubbub; it’s just that I didn’t see it.

The city has changed dramatically, as you probably know, since then. At that time, it was kind of down at the heels. It’s really been fun to be part of and enjoy the development of Washington into a fabulous city.

LD: Where did you go with your journey once you graduated from Georgetown in 1984?

JSR: I clerked on the Fourth Circuit U.S. Court of Appeals for Judge James M. Sprouse and that took me to West Virginia. Then I went to Minneapolis for a year and a half at Dorsey & Whitney. I’ve been back in D.C. since 1987.

LD: Did your clerkship teach you any valuable lessons about how you wanted to pursue your career, or why you didn't want to live in West Virginia?

JSR: I loved living in West Virginia. I had a wonderful time. I learned how to make a quilt and did a lot of square dancing and clogging and hiking!

LD: You can find amazing things anywhere, right? So when you moved to Minneapolis, did you intend to stay?

JSR: I was ready to settle down. I was looking for a wholesome place to live and I thought Minneapolis was quite wholesome. I also wanted to do corporate law for a while because I had loans to repay. I was very conscious of that.

LD: And then in 1987, you returned to D.C. and started at Piper Marbury. Perhaps in a foreshadowing of your future career, it took just three weeks before your senior partner decided to move to Shaw Pittman, which later merged with Pillsbury. And you made the move with him. You first did litigation, including a nuclear reactor dispute and the only civil litigation to come out of Iran-Contra, in which you helped win the highest Rule 11 sanctions at that time. Then, after a stint in Australia as a lawyer, you moved to the transactional side and became a standout technology lawyer, especially in communication satellites.

At some point, though, you moved away from substantive law practice, telling Pillsbury’s managing partner you’d like to work with the committee focused on talent development. That was quite a novel move. What inspired you?

JSR: I thought we could be more strategic about our recruiting and about how we developed lawyers at the firm, both partners and associates, and about our alumni relationships.

I had some experience in this. I’d worked to recruit to the firm a law boutique that specialized in telecommunications. They were adept in regulatory work on communications satellites, which had become one of my specialties.

I believed we really needed to be thinking about our talent pipeline from our first contact in the law schools to, basically, the grave. The committee broke that span into stages – from recruiting, which covered contact before they joined Pillsbury, to their tenure at the firm and then their career afterward, when they might be roughly comparable to university alumni.

I thought we could get buy-in across the partnership if we started first with the partners and figured out what they most needed. What they most wanted was training in business development, so we began there, and we were very successful. That experience has been helpful to me in advising lateral candidates because it gave me more insight into how to build a successful legal practice.

LD: While you had worked at improving the firm’s talent acquisition and development, becoming a professional recruiter was a new career. What led to the change?

JSR: It was awkward to be practicing law in the firm – not unethical, not prohibited, but still awkward – after my husband was appointed Chief Justice. Also, I had two young children. At brunch with friends on New Year’s Day in 2007, one suggested I become a recruiter.

I said, “Really? I've never even returned one of their phone calls!” But in 30 seconds, I could see this made tremendous sense. It was like a lightning bolt. Another friend at the brunch was then the lateral recruiting partner for a prominent law firm with offices in D.C. and offered to introduce me to Major, Lindsey & Africa. Fast forward a few months and I started there.

LD: You built up a tremendous reputation as a recruiter at Major Lindsey. What led you to join Macrae, then known as Mlegal, in 2019?

JSR: I wasn’t looking to move – which is often the case with our candidates in recruiting. CEO Carter Brown, whom I knew from Major Lindsey and considered a wonderful person and business leader, contacted me. I’d heard great things about the firm – which rebranded to Macrae about a year ago – but I agreed to meet mostly out of courtesy to him. When we met, he explained what they were trying to do, and I thought, "Wow, this makes a lot of sense."

They were pulling together top recruiting talent in the world’s four most important legal markets, Northern California, New York, D.C., and London, and they wanted me to open the D.C. office. The firm had a strong foothold in the San Francisco Bay Area, where founder Joe Macrae had set up shop years earlier, and they’d just expanded to New York and London. The next step was D.C. The goal was to be an elite transatlantic boutique squarely focused on partner-level talent, and a firm that did things at the highest levels. Did I want to be a part of that?

LD: And of course, given your history of making bold moves, you said yes.

JSR: I decided I did. In terms of being entrepreneurial, it was an exciting opportunity to be on the ground floor of a firm that already had an excellent reputation and big, but realistic, ambitions. When I joined Macrae it was nimble and at the beginning of its cultural formation, because while the firm wasn’t “new,” per se, the direction it was going in was. New partners could really influence and implement best practices. While each of us was experienced and successful, the firm didn't have an encumbering legacy. We could just ask, “What is the best way to do this?” and then do it across the board.

We've spent the last two years driving best practices throughout the firm, from the most senior recruiters to our knowledge managers, who are fabulous and provide tremendous support to make us more effective and efficient recruiters. The D.C. office has grown to eight. We spend alternate Tuesday afternoons discussing how we can do things better, candid conversations that can be excruciating sometimes but the result is that we’ve been continually improving as individuals, as an office, and as a firm. The system of shared intelligence we’ve developed, and the total transparency each of us has into what’s going on across the firm, from our projects to the financials to internal hiring, is pretty incredible.

LD: I love your insight about focusing on building toward what’s better. What are some of the tips you offer candidates in this vein?

JSR: It really depends. I start with listening to what they have done, the pluses and minuses of their past, and where they would like to go. Sometimes they know, sometimes they don't know. The overarching theme is that they need to take charge of their career; nobody else will do it for them. They need to listen to their own heart about what they really like and don't like, and we go from there.

LD: Is there anything unique about what it takes to make it as a great lawyer in D.C. as opposed to, say, New York or San Francisco or London, that you share with them?

JSR: My focus now is on highly experienced lawyers – government lawyers and law firm partners. But when I was executive partner for talent development at Pillsbury, I worked with associates as well as partners and had a weekly luncheon with first-years, where I brought in lots of different speakers. One thing I thought was really important for them, if they foresaw a long future in Washington, was to serve in the federal government at some point to understand how it works, to get hands-on experience with the agencies, with the laws, regulations and processes, and to develop a network.

LD: Any advice for your client base, or for lawyers more broadly, on making smart career choices at a time of such rapid change in the industry?

JSR: You need to be the driver of your own career. Just as you assess the fitness of your children’s schools every few years, in this rapidly evolving legal market you should take stock of your own situation every few years and determine whether it supports you in achieving your own goals or whether you should seek better opportunities.

LD: That makes a lot of sense. Considering the breadth of your career, what would you say has been your favorite job?

JSR: I’ve enjoyed each of them. In my pre-professional life, I loved waitressing. I also loved teaching and my transactional work. Now, with recruiting, it feels like the perfect choice for this stage of my career, where I feel as if I have so much relevant experience to guide people through what can be a very important and stressful transition in their life. What are the four big decisions? Getting married, buying a house, having a baby, and changing jobs.

I'm with them for the job transition – which sometimes coincides with getting married, having a baby or buying a house – and it's very gratifying to help people during a critical phase in their lives. There’s nothing else I would rather be doing now.

About the author: Katrina Dewey is the founder and CEO of Lawdragon, which she and her partners created as the new media company for the world’s lawyers. She has written about lawyers and legal affairs for 30 years, and is a noted legal editor, creator of numerous lawyer recognition guides and expert on lawyer branding. She is based in Venice, Calif., and New York. She is also the founder of Lawdragon Campus, which covers law students and law schools.