Chicago includes about 200 University of Virginia School of Law alumni among its ranks, including partners at prominent firms, general counsel at businesses and entrepreneurs, among others. We talked to several alumni to gather their work experiences and tips for students and graduates on how to succeed there.

The UVA Law Network is an occasional series on careers for graduates. The school's 20,000 graduates are located in 50 states and more than 60 foreign countries.

Advice from Alumni in Chicago

Douglas Bouton

Douglas Bouton '10

President and Chief Operating Officer, Halo Top Creamery

How did UVA Law prepare you for your practice or career choices? 
I took an interesting career path in that I went to UVA Law and now I'm president and chief operating officer of Halo Top Creamery, an ice cream company. Straight line from taking the bar to making ice cream, right? When I applied to law school, I knew I didn't want to be an attorney. Frankly, I didn't know what I wanted to do other than not enter the job force yet. Among the many ways that UVA Law prepared me for my career (in ice cream of all things), the most important is undoubtedly the people. I think the people are what make UVA Law so special, enjoyable and distinguishable from other law school experiences. The people with whom I became friends at UVA Law have helped my career and Halo Top in both tangible (UVA Law friends invested in Halo Top when we desperately needed the money — special shoutout to Stephen Wendell '10 and Matt Farmer '10) and intangible ways (e.g., challenged me to grow and mature intellectually and as a person). I wouldn't be where I am today in my career without the people of UVA Law.

Andrew Boutros

Andrew Boutros '01

National Co-Chair White Collar, Internal Investigations, and False Claims Team, Seyfarth Shaw

How did UVA Law prepare you for your practice or career choices?
UVA Law gave me the confidence to know that I could tackle any legal problem and that I could be successful in whatever legal specialty I pursued. I gained that confidence from taking on a rigorous curriculum that was both challenging and flexible. In class and through my research with the late Professor Jeffrey O’Connell, I was encouraged to think through problems and to offer practical solutions. I was also encouraged to explore new areas of the law and think outside the box. Plus, I was learning from some of the best in the business. The end result was that I graduated from the Law School with a strong legal foundation that I knew I could apply across subject matters and areas of specialty. Today I am one of the chairs of my firm’s White Collar, Internal Investigations and False Claims Team. Along the way I clerked on the Sixth Circuit; worked for years at a top international firm in D.C. doing white-collar work; helped that firm establish one of the country’s leading [Foreign Corrupt Practices Act] practices well before the FCPA’s rise to prominence; and worked for years as an assistant U.S. attorney in Chicago, where I handled complex frauds and financial crimes. As an AUSA, that outside-the-box thinking that UVA encouraged later enabled me to successfully prosecute the two largest food fraud and customs fraud cases in U.S. history and also convict the largest drug trafficker on the now-shuttered dark website known as Silk Road.

Do you have any advice for new UVA Law grads wanting to work in Chicago?
UVA Law grads are in demand everywhere — and the Chicago market is no different. With two elite schools in the Chicago area and a third only a few hours’ drive away, many law firms in Chicago delight at the opportunity to pick up top talent from a top-10 law school like UVA, which is outside of the Midwest. That is especially true for those UVA Law grads who have ties to Chicago — so, emphasize those local ties. Because the UVA Law experience is different from that of many other schools, I would encourage UVA graduates to showcase and speak about their strengths and values — meaning their team-oriented mindset, strong work ethic, leadership skills, passion for the law, can-do attitude and well-rounded nature. Legal employers don’t just want employees — they want dedicated professionals who will care about client problems as if they are their own. Showing that level of interest and sincerity can only help distinguish you from other candidates. And, of course, connecting with alums is also always helpful and can be the first step to getting your resume to the top of the pile or to getting an interview.


Karen Owen Gibbs '92

Partner, McDermott Will & Emery

How did UVA Law prepare you for your practice or career choices?
The culture of the Law School fosters congeniality and cooperation, which are highly important for success. I believe that the "emotional intelligence" that Virginia graduates display derives from that culture. As I've progressed in my career, the softer skills have been highly important. I credit UVA with preparing me to help my clients navigate opportunities and challenges from a 360-degree perspective.


Todd C. Jacobs '89

Managing Partner, Shook, Hardy & Bacon

How did UVA Law prepare you for your practice or career choices?
I’m a commercial litigator and the managing partner of the Chicago office of a 500-plus lawyer litigation firm. UVA Law prepared me for this role in many ways, but two stand out. First, by offering a curriculum and faculty that really teach students to think critically. So much of what we do in private practice requires a logical assessment of complex situations, and the ability to provide legal advice and options, often without the luxury of time. Many cases we handle do not have straightforward answers, and new subject matters arise daily. It’s within these gray areas that I appreciate how UVA Law teaches students to think through complex questions. To be honest, I don’t really remember much of the substantive law from classes such as Corporations and Criminal Procedure. But I do remember how professors in those classes taught students to think through the issues presented. This problem-solving capability will stick with you for your whole career. Second, and just as important in my view, UVA Law is good at valuing people and teaching people skills. Students are encouraged to get to know one another both in and out of the classroom. Individuals matter. Having fun matters. It’s not all about the books. I think you’ll find the practice of law in the real world involves the kinds of people skills and values that UVA Law encourages. Get to know your clients, be interested not only in their problems, but also in who they are as people. I think you’ll find this to be not only a recipe for a more successful practice, but also a more fulfilling way to live your life. In conclusion, one data point: I don’t think I’ve ever met a UVA Law graduate who didn’t enjoy and value his or her three years in Charlottesville.

Do you have any advice for new UVA Law grads wanting to work in Chicago?
Feel free to call me at (312) 704-7705. Chicago is a big place and market. There are many opportunities: Big firms, regional firms, innovative startups, government service, public service, in-house. We’d love to hear from UVA grads who might be interested in working here. I’m sure there are many other firms in town in a similar position. So, if you really want to evaluate the opportunities available, you’ll likely need to explore beyond the UVA placement office. I’d be happy to do what I can to point you in the right direction.


Kenneth P. Kansa '99

Partner, Sidley Austin

How did UVA Law prepare you for your practice or career choices?
UVA Law prepared me as a lawyer in more ways than I can count, but what stands out is how the Law School prepares you to advance your client’s interests and arguments in a collegial and respectful way. Law is inherently adversarial, of course, but in Charlottesville we learned quickly that your competitor can also be your friend, and that a cooperative approach to problem-solving often gets the result you want with much less time, cost and grief than a bombastic approach. Most judges and clients I’ve seen ultimately tend to prefer the lawyer they see as the consensus-builder over the one they see as shouting the loudest.

Do you have any advice for new UVA Law grads wanting to work in Chicago?
Be clear about why you’re interested in Chicago if it’s not evident from your resume. Chicago is a less traditional destination for UVA Law graduates, so it’s usually a point of interest. It may simply be that it’s a city that you’d like to give a try – which isn’t a bad answer – but explaining your interest up front is often a big help.


Andrew McGuire '99

Deputy General Counsel, Caterpillar Inc.

How did UVA Law prepare you for your practice or career choices? 
Since graduating from UVA, I first practiced law in a large firm, and now I practice in-house at a large corporation. Over the years, I have really come to appreciate the basic foundation of legal thinking and problem-solving I obtained at UVA. A solid grounding in those fundamentals has allowed me to be flexible over time in several different roles.

Do you have any advice for new UVA Law grads wanting to work in Chicago?
Chicago is one of the country's great cities, and there is a lot to enjoy. Chicago is some distance from Charlottesville, but the local bar consistently values UVA grads highly. I also found the local professionals to be welcoming toward new lawyers from everywhere. You do not have to be from Chicago to be accepted in Chicago and succeed in Chicago.


James E. Pfander '82

Owen L. Coon Professor of Law, Northwestern University

How did UVA Law prepare you for your practice or career choices? 
As the old saying goes, students who really enjoy law school often end up as law professors. That’s what happened to me. I had a great time at UVA Law, both on the softball field and in the library. My classmates told me I was too unformed to teach immediately upon graduation, so I clerked and practiced for a few years before picking up my first piece of law school chalk. Now these many years later, I credit UVA for sparking my interest in law, in history and in the surprisingly rewarding details of federal jurisdiction and government accountability, the subjects to which I’ve devoted much of my intellectual energy.

Do you have any advice for new UVA Law grads wanting to work in Chicago?
It’s a great town, with distinctive neighborhoods, a thriving cycling culture and local festivals that celebrate our many ethnic communities. Buy a good coat and sensible shoes for the winter months and plan to spend much of your summer outdoors. To balance the demands of work, find an organization that needs volunteers and pitch right in; it’s surprisingly easy to become a part of something bigger than yourself.


David Saunders '07

Partner, Jenner & Block

How did UVA Law prepare you for your practice or career choices?
I believe that to be good at anything, you have to start by learning the very basics. To that end, I learned two of the most basic but important things about being a lawyer. First, I learned how to think like a lawyer. While that may sound silly, I learned as a 1L that there is a very real difference between writing a college paper and writing a brief. Learning how to think critically about a legal issue is the foundation upon which I have built my litigation practice. Second, I learned that the best results are almost always the product of cooperation. Whether it is brief writing, developing litigation strategy or preparing for argument, the best results come from teams working together, testing theories and ideas. In short, UVA provided a strong foundation upon which I was able to then build my legal practice.

Do you have any advice for new UVA Law grads wanting to work in Chicago?
If you are thinking of working in Chicago, be able to answer a simple question that oftentimes people do not have a great answer for: Why do you want to be in Chicago? I or anyone who has spent more than a day here might tell you the answer to that question should be pretty easy to come by. However, Chicago sometimes does have a "second city" complex. Reassuring firms that you really want to be in Chicago as opposed to staying on the East Coast is an important thing that people often overlook in their preparation for interviews. Beyond that, network. Reach out to alums here in Chicago and talk to them. If you are here visiting family or friends, ask if an alum has time for some coffee to talk.


Paul Stroka '05

Director of Legal Solutions, Pangea3, Thomson Reuters Legal Managed Services

How did UVA Law prepare you for your practice or career choices?
UVA Law offers a unique combination of a first-rate legal education and an engaging environment in which law students can form deep-rooted personal (and later, professional) bonds. This combination of a UVA Law education and a UVA Law network is unmatched, and has helped me develop the expertise and opportunities that have driven my professional success during and after my time as a practicing attorney.

Do you have any advice for new UVA Law grads wanting to work in Chicago?
Come to Chicago, a world-class city with small-town charm. There are not as many UVA Law grads here as there are in New York City, D.C. and Atlanta, so I would strongly urge you get an internship here if you can during school so you can start to build contacts. The legal market is difficult for junior attorneys, so build your skills through clinical or pro bono work. More than ever before, employers want junior attorneys to hit the ground running — be ready.


More in the UVA Law Network Series

200+ Alumni

Leaders in Chicago

Douglas Bouton '10 
President and Chief Operating Officer, Halo Top Creamery

Andrew Boutros '01 
National Co-Chair, White Collar, Internal Investigations and False Claims Team, Seyfarth Shaw

Bruce R. Braun '89 
Partner, Sidley Austin

Marisa Bryce '93 
CEO and Co-Founder, ConversePoint

Robert G. Byron '76 
Chairman and Co-Founder, Blue Vista Companies

Eva Chess '85 
Vice President, Communications and Marketing, American College of Healthcare Executives

Mareile B. Cusack '85 
Senior Vice President and General Counsel, Ariel Investments

Karen Owen Gibbs '92
Partner, McDermott Will & Emery

Todd C. Jacobs '89 
Managing Partner, Shook, Hardy & Bacon

Kenneth P. Kansa '99 
Partner, Sidley Austin

Ronald L. Marmer '77 
General Counsel, 
Chicago Board of Education

Andrew McGuire '99 
Deputy General Counsel,
Caterpillar Inc.

Paula J. Morency '80 
Franchise and Distribution Client Service Team Leader and Partner, Schiff Hardin

Allegra Rossotti Nethery '95 
Pro Bono and Philanthrophy Partner, Seyfarth Shaw

James E. Pfander '82 
Owen L. Coon Professor of Law, Northwestern University Pritzker School of Law

Katherine Monahan Rohrbaugh '07 
Litigation Counsel, Kraft Heinz Company

Brenda Russell '87 
Director, Pricewaterhouse Coopers

Lee Anne Russo '80 
Partner, Jones Day

David Saunders '07
Partner, Jenner & Block

Paul Stroka '05
Director of Legal Solutions, Pangea3, Thomson Reuters Legal Managed Services

Mark B. Tresnowski '86 
Managing Director and General Counsel, Madison Dearborn Partners

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