Sullivan Summer
Gap year
Formerly, Director, People Experience & Technology at Amazon
New York, New York
Other affiliations include associate, Littler Mendelson
JD Benjamin N. Cardozo School of Law
BA College of New Rochelle
Labor law expertise leads to business career at Amazon
On having mentors in business
On the two different paths to success in a company
On managing people in a functional area where you are not an expert
Listen to interview:
Full Transcript
ex judicata: Thanks for taking the time to talk today, Sullivan. I really appreciate it. So, I’m also a Cardozo graduate.
Sullivan Summer: Oh, fantastic. The one thing I didn’t have time to do was an Internet search to learn a little bit about you. I feel like I’m wrongfully flying blind, that I don’t know anything about you.
ex judicata: OK. So, here’s a little bit about me. I went to Brandeis University, then Cardozo, and after graduating I worked for a short time at a real estate company. Then I went to American Lawyer. I worked there for 22 years as the managing editor and marketing liaison. I did acquisitions and then I went to a couple of other places before establishing my own company. I work with global law firms and other businesses on marketing.
This particular project that I’m working on now is really interesting because it focuses on helping lawyers transition to other careers. I’m interviewing people who have done so successfully as a guide to help people who want to make that change. Many people are unhappy, want to go corporate, or just want a change. So that’s what we’re looking for here.
After Cardozo, I know you worked at firms and you had a focus in employment, So tell me how and where you started after law school.
Sullivan Summer: In the interest of full disclosure, just so you don’t get surprised later on, I actually left Amazon at the end of last year. I have taken the year off.
ex judicata: Wow! Good for you.
Sullivan Summer: So, I’m currently in a gap year. I never took a gap year in my whole life. But back to your question, I discovered in law school that I knew I wanted to do traditional labor law. I didn’t know what it was before I entered law school, but I sort of fell in love with it and I knew that’s what I wanted to do.
I graduated in 2004, which means 9-11 was my second week of law school. The market was still pretty bad in New York City when I was graduating. I wound up in Atlanta at Fisher & Phillips LLP, the oldest labor firm in the nation, a 200-attorney boutique firm. I was the only woman in the traditional labor practice group. I was the only person of color, and I was the only person under 40. Traditional labor is like an all-white-guys area, quite frankly. But I loved it.
ex judicata: I noticed you also worked at a second labor firm before going to a corporation.
Sullivan Summer: Right. I was at my first firm for two years. I got recruited by a friend to a different firm, Littler Mendelson. At the time, I’m not sure if it still is, Littler was the largest labor and employment boutique in the nation.
So, I went over to Littler, still in Atlanta. As I was nearing the five-year mark, I started to do this soul searching. Do I want to be a partner in a law firm? I loved Littler. I loved who I worked with. I loved the firm, but I just didn’t know if I wanted to be a partner in a law firm. Littler and most of the firms in Atlanta had a seven-year partnership track and I was on track for partnership.
We had done some work for a client who was appealing its case. And it was sort of working its way to the Supreme Court. The client had a really good case. But then, at some point, the client just tapped out. They were like, you know what, we’ll take our lumps and do it. So, what it comes down to is that it doesn’t matter if you’re right or what you’re doing is interesting or creative. If the client doesn’t want to pay for it, you’re not going to do it.
ex judicata: Right. That’s a business decision. Lawyers tend to struggle with that. You have good advice and a strong case, but the path forward is a business decision that the client’s going to make. You can advise them all you want regarding the law, but they make the ultimate decision, good or bad.
Sullivan Summer: Yes. I understood the clients that I worked with. I was working predominantly in labor relations work. So I was working not just with their lawyers, we were working with their business leaders and their HR leaders. I just thought what they were doing was more interesting than what I was doing. We were sort of doing the same thing. We’re sitting in contract negotiations, so we’re having the same experience, but what they were doing looked like more fun than what I was doing.
ex judicata: So was that kind of your “ah ha moment” that led you to the corporate world?
Sullivan Summer: Yeah. And it was all really serendipitous. While I realized that I had the skills to one day be the VP of labor somewhere, I felt that I didn’t know how to do anything else except labor relations. So I decided to get my MBA. I started courses online through Northeastern University while I was still at the firm. I took the slow road, like one class a semester while working full time. Then I got a cold call probably because I was in Atlanta. Coca-Cola Company was looking for someone to join its labor relations department. Littler was super supportive. It’s good to know people in companies. I just went to the partner I worked with and told him that Coke was looking for a labor relations manager. He said, “Yeah, I know. Do we know anyone?” I asked, “What about me?” Coke was a client. Littler wasn’t its sole firm, but Coke was a client, so there were some connections there. And I got the job.
ex judicata: Really? The job just came to you out of the blue? You simply got a call. That’s incredible.
Sullivan Summer: Yeah. It was a third-party recruiter who was just trolling law firms, calling associates one after another. But there were so few people that did traditional labor at the time and even still today.
ex judicata: My daughter actually works for Nasdaq and she’s in charge of global human strategy for tech. So that relates to what you do. She went to Cornell to the ILR School.
Sullivan Summer: Yup. I worked with a lot of people that got their undergrad from the ILR School a ton of.
ex judicata: Were you scared making the change?
Sullivan Summer: Yes. I didn’t know what I didn’t know. I had never worked in a corporation. I started working at 14, but I worked for nonprofits. All through undergrad, I worked for nonprofits. I worked for two years for the government before I went to Cardozo. All of my internships were government internships.I also never worked for a firm before I graduated from law school. The first firm I ever worked for was Fisher & Phillips right out of school, and a firm is not like a traditional corporation. It’s quite different. Coke was the first corporation I ever worked for in my life. I look back now. I was totally ill-prepared. Well, I was prepared from a “smarts” standpoint. I was intelligent. I learned the job. But from a corporate environment standpoint, I was totally clueless. I had no idea.
ex judicata: What do you wish you knew before you went to work at Coke? What should people who are thinking about making this change to a corporation be watching for?
Sullivan Summer: Well, one thing that I think is important is to separate out the idea of in-house corporate versus what I was doing. I never worked for a corporate law department. I want to make sure that when people are thinking about options, like in-house, they understand that that’s a whole other avenue than what I was doing.
There are some corporate culture things that I suspect are the same no matter what corporation you work for. They’re not company-specific things around how you manage your time and what the day looks like. I think in a corporate environment, you’re ruled by a calendar in ways that lawyers don’t understand at all. I was scheduled within an inch of my life, literally every minute. Still, I was more than happy to walk away from six-minute billing. I never missed it for a minute.
ex judicata: Billable hours can be so stressful. Did you find that it was less onerous working for a corporation?
Sullivan Summer: No. It’s a myth that corporate life is easier.
ex judicata: I know somebody who went to Goldman or one of those other big companies and she said that she was working harder and longer hours than when she was at a firm. So I think that’s a big surprise for people. What differences did you find?
Sullivan Summer: What is different is a feeling. You can’t see it. The feeling of the ticking clock goes away, that whole six-minute billing pressure. You don’t wonder if it’s okay to take a walk around the office after working 10 hours. But it’s still a 14-hour day. We’d joke that you’d have to pick which meeting to be late to so you could go to the bathroom. Seriously? I never looked at the clock one minute except to be like, wow, it’s 4:00. I used to joke at 5:00 that it was the start of the second shift.
ex judicata: It sounds like it was a long, long day. People definitely think they will have an easier life at a corporation.
Sullivan Summer: It’s a myth that it’s less work.
ex judicata: Was there anything you did to prepare yourself for the change?
Sullivan Summer: I was lucky when I went to Coke because I worked for a very small department. My boss was a labor relations guy. It’s typically lawyers and HR people in the department. So you’re sort of surrounded by people that do have your same background, even though you bring a legal perspective, a sort of nontraditional kind of thing. So I had a boss that had been in law firms, and then he’d been in the corporate environment for 10 or 15 years. He gave me a lot of guidance. His office was across the hall. He knew what I was up to all the time. I had a lot of handholding that, at the time, I didn’t realize was handholding. I realize it now. I don’t know if I would have been successful without that. I don’t think the transition would have been as smooth.
ex judicata: Yeah, I think people need guidance whether it’s from a formal or informal mentor the same way that I think they do during those first years after law school. Having a mentor is hugely important.
Sullivan Summer: And I also think that every corporation has its culture and cultures can be very different. I think having a person to help in the transition is important and it’s best if that person is someone who’s inside, someone who understands the specific culture of that company.
I was only at Coke for two years. Coke bought its largest subsidiary. It was sort of like the small fish swallowing the big fish. I had the option to stay or take a package. At the time, my boyfriend who later became my husband was living in Boston. I was living in Atlanta. So, I’m thinking, let me get this straight. You’ll give me a career coach and you’ll give me a pile of money to go find a different job? Great. So I left and went to Amazon, where I wound up playing that mentor role. I frequently got assigned to be the sort of onboarding buddy for people coming, especially people coming out of law firms.
ex judicata: So I think when a candidate is interviewing, it’s important to ask about mentorship at the company. Is there some sort of program? How do you help new people transition into this role?
Sullivan Summer: Some companies have those types of programs, but a lot of them don’t. So, candidates should ask about how the company onboards. What does onboarding look like? I think that’s the better question.
ex judicata: I went to a law firm and the onboarding was insane. You spent days in front of a computer learning a system and learning about security. Your head is swimming with information. It really would have been good to have somebody there as your guide to kind of walk you through, like a big sister, you know?
Sullivan Summer: That would have been great. Some of it is like the spiel I used to give at Amazon. I was there for 12 years so at the time that I left, I was more tenured than 99.99% of the people there.
ex judicata: There’s so much to learn.
Sullivan Summer: Right and that’s normal.
ex judicata: Then there’s the culture. You have to learn how it all operates. Each corporation is different and understanding the culture is key.
Sullivan Summer: Right. Is it a company where you’re expected to fake it till you make it or is it a company where they value asking questions? They’re totally different cultures. If you take the wrong approach, that’s a quick way to lose people’s trust in you.
ex judicata: So, that’s an important consideration. People should be learning about the corporate culture and making connections with those in the know at a company so that they can do that.
Sullivan Summer: Yeah. Culture is sort of everything. At a firm, there is an equalizer, billable hours. It doesn’t matter what your job is, you have to bill the hours. There’s no such equalizer in the corporate environment.
ex judicata: That’s true.
Sullivan Summer: So what does success look like? What am I measured on? Most companies have that. But still, you and I could have the same job. In a sense, we’re measured on the same things. But I’ve been in that environment. I know there are other things that aren’t written down, that aren’t quantifiable, that are going to say that you’re more successful than I am or I’m more successful than you. And different opportunities will come with that.
ex judicata: That’s so true. When I was at The American Lawyer, I structured things so that I worked with the most important people, the most valued, which made me more valued because I had relationships with them. How you’re building your structure and your support network, who you’re working with, you need to understand all of that. You have to ask questions. I think a lot of it is asking questions. It’s probably the best advice when you’re going somewhere to understand what you’re going into and to ask the right questions so you can get the information you need to have the best chance of succeeding. You need to understand what the expectations are.
In terms of coming into a corporation like Amazon, where do lawyers really stand out as being great candidates? You don’t always match up with all the skill sets. In a lot of instances though, lawyers have readily transferrable skills. What makes a lawyer a good candidate?
Sullivan Summer: So, one of the great things about Amazon especially, is that once you have a foot in the door, they didn’t care what your background was like. I used to joke and say that every two years I asked for a job I was minimally qualified for and they’d give it to me. I did all kinds of stuff that I probably wouldn’t have been able to do in other companies. I think that when you start out, when you first make the change from a law firm to a corporate environment, they’re hiring you for your functional expertise. I knew about labor law. They’re hiring you for your knowledge.
ex judicata: Right. You have that legal perspective.
Sullivan Summer: Yeah. It’s a broader lens. I also found both at Coke and at Amazon that I was very highly valued by the lawyers as well. I was happier working in a nonlawyer role. I felt that if we needed legal cover, we should call one of the lawyers to advise us. But the lawyers really appreciated knowing that I wasn’t going to do anything stupid. I knew exactly how far to go before picking up the phone and saying, “I need you.” I knew exactly in a conversation with my business leaders, my colleagues, when to say, “Stop talking. This needs to be a privileged conversation. Call the lawyers.” They really appreciated that I had that breadth of knowledge.
ex judicata: I think it’s also because of the way you think.
Sullivan Summer: At least, in my experience in the labor and employment vein, the stuff that’s illegal is pretty obvious. But I wound up in my career, particularly at Amazon, a couple of different times owning HR compliance. I’m a labor attorney that had to take an employment class once. I don’t know data privacy and those sorts of things. You wind up having to stick a toe in. But because you know how to think about it, you can grasp the important things really quickly, more so than someone who doesn’t have a legal background. I’m not a data privacy expert. I never will be. But I can engage in an intelligent conversation and make business decisions like that.
ex judicata: A lot of it is issue spotting. You may not know the solution, but you know when there’s an issue and you know how it should be addressed. Some things you can answer, and some things have to go further. You recognize risks. I think the legal mindset absolutely makes a difference.
Sullivan Summer: Yeah, that’s exactly the term, issue spotting. That’s really huge.
ex judicata: Among the greatest challenges is adapting to the corporate world.
Sullivan Summer: That’s probably the first big challenge. So I think there are two big challenges and they’re highly dependent on the track you take. If you get hired for your knowledge, and you’re in an individual contributor role, that’s what you do. It’s a different environment, but it’s not that different than the legal role. If you start on a people leadership track, which I did, my biggest team was 1,400, you need a different skill set. You have to be a good leader. Someone that’s a good lawyer isn’t necessarily a good people leader. It’s the same no matter what your job is, right? Leadership is a skill in and of itself. You may or may not be good at leading. So that’s an adjustment.
I had another big adjustment though. I had been in labor relations, employee engagement, and employee relations at Amazon. I was there for about four years in various roles and decided I really loved Amazon, but I was tired of the work I was doing. I wanted to do something else. I remember the first time I had a job, though, outside of labor relations. I didn’t know anything. I realized really quickly that I had people I now managed who had been doing this thing for 20 years so there was no amount of learning that I was going to be able to do to make me know more than them.
ex judicata: Well, that’s where listening comes in. Lawyers like to talk, but lawyers need to listen too. So it’s important to take a step back and be more of a listener when you’re in the corporate context. I think that applies in any job. You have to take the time to listen and learn before opening your mouth with an opinion.
Sullivan Summer: Yes. It is also where issue spotting is important. I had somebody considering changing careers and she asked, “How do you manage people in a functional area where you’re not an expert?” At one point, I had a huge software developer team. I was managing software developers. I can’t code. I don’t know anything. I said, “You’ve got to be able to ask good questions.”
ex judicata: Yes. There’s your issue spotting. It’s about asking the right questions. Earlier you mentioned having minimal qualifications but taking the plunge in pursuing opportunities. Men readily apply for jobs without having all the qualifications figuring what do they have to lose. Women, however, won’t apply unless they have nearly all of the qualifications for a job.
I think a lesson here is that sometimes you need to stretch a little. It’s great if you can get a good mentor to guide you. Don’t just think you’re not qualified. Look at how your skills translate into a role. I think there are a lot of skills like issue spotting that translate well for a lawyer. What other skills do you feel you had as a lawyer that were really helpful in going from law into a business role at a corporation?
Sullivan Summer: It’s a little bit of issue spotting, but you talked about listening. I think client-facing lawyers have to be really adept at listening to the words coming out of their client’s mouth and then doing the calculations in their head about what the legal ramifications are. Then the lawyer has to think about what’s important, which probably isn’t the same thing that the client may think is important based on what’s coming out of the client’s mouth. I think it’s the same at a corporation. I have a job to do. This is what I have to deliver. I have bosses. The bosses want to see X, Y, and Z. I hear them say that’s what they want. Then there’s my understanding of what they really want.
ex judicata: You have to consider what they say in the context of their business goals, their long-term strategy, as well as in the context of their short-term goals, and then think about how it all fits together. That’s something lawyers learn on the job. That skill is important in any role.
Sullivan Summer: Yes. It’s that experience.
ex judicata: Shifting gears, I know you’re a major long-distance runner. What the heck motivated you to do that?
Sullivan Summer: When I was nearing 40, I decided I wanted to run a marathon. It was something I wanted to check off on a bucket list. I wanted to be able to say I ran a marathon. I worked out a lot and was pretty fit. But I was not a runner. So I ran a marathon, and I was like, “This is great!” I knew I wanted to run. There were long-distance races I had discovered like a 100-mile race. I decided this is what I wanted to do. So I just started running a bunch. I’m only a mediocre runner. It’s really important for me to say that because people picture me winning these races. But I’m in the middle. I’m almost always in the middle although sometimes I’m at the end. Typically, I’m in the middle. So I’m doing these really long distances in the middle of the night. There are risks of frostbite and hypothermia and all this kind of stuff, but I realize that running is a safe place to take risks. I can try a new distance. I can try new things. Sometimes I fail. Nobody cares. It doesn’t matter. I don’t have Nike signing my paychecks. Nobody cares how I do. I can try something really hard that has no consequence at all and that starts to put things in perspective.
When we have opportunities at work, whether we’re given them or we seek them out, I think women especially immediately think they’re not totally qualified. So if I try it and I’m not perfect at it, I’ll fail and I’ll get fired and then I can’t pay my rent. They think that’s the way it’s going to go.
ex judicata: But usually, if you’re a good employee and you’ve been good at something, if you don’t do well in a new role, then they’ll look for another solution for you. Because you’ve proved yourself and they want to be able to keep you. They recognize that the new role just wasn’t for you. I used to run, but I ran very short races. It was a single mile, and I ran it at 5 minutes and 7 seconds.
Sullivan Summer: I’d rather run 100.
ex judicata: I tried longer but it wasn’t for me. Your stamina and going that extra mile, as they say, translates in work to that commitment, determination, follow through, and recognizing you’re not always going to be the best. I think the idea of being in the middle, which is where most people are, is a life lesson, a realization that you can’t excel at everything. Not everybody’s going to be perfect at everything but finding what you enjoy and doing that is a great thing. So, what’s your game plan going forward? Are you looking at ideas or are you just taking a break for now?
Sullivan Summer: I’ve taken off just 2023. For me, the road not taken as a kid was writing so I’m taking time to write. I enrolled in writing programs. They’re time-bound. I’ve been working since I was 14. I worked my way through school. It feels nice to have a little break so I’m writing, and I will go back to work in 2024. I don’t know exactly what I’m going to do yet. I’m unlikely to go back to Amazon. It’s time for something else.
ex judicata: You’ve made a lot of changes recently. You moved to New York, divorced, and changed your name. What does changing your name do for you?
Sullivan Summer: It was identity reclamation, for sure.
ex judicata: So, identifying who you are, working on who you are, and being the person you want to be? That sounds like a good thing and something you can do at any point.
Sullivan Summer: Yes. I think I’m super inspired. I don’t have kids. I’m a Gen Xer raised by Boomer parents and in many ways we were never allowed to just be. So now that is what I’m doing.
ex judicata: Sometimes you just have to stop, breathe a little bit, and see where you want to go next. It’s great that you’re doing that. You know, people are afraid to do that. Good for you.
This has been great. I think that there’s some really good advice in there and just the sense of finding yourself, being yourself, listening, and having confidence in yourself are all really good messages here. I really appreciate your time. Thank you.
Sullivan Summer: Thank you.
ex judicata: I wish you the very best. Whatever you decide to do, I think it’s going to be great. So thank you so much. And have a great rest of the day.
Sullivan Summer: You too. Thank you.