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Tracy O. - Vice President, Deputy General Counsel

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Title: VP, Deputy General Counsel, Global Litigation, Employment and Compliance
Location: Chicago
Joined: 2019
Preferred Pronouns: She/Her/Hers

Chicago native, Tracy O’Flaherty, tells us about her role as VP, Deputy General Counsel, how her team is staying connected as we continue to work remote, and which pre-Covid activity she can’t wait to get back to!

Tell us a little about your role and your team.

I am the Vice President, Deputy General Counsel of Groupon heading the global litigation, compliance, regulatory, employment and security functions of the company. My team is composed of a wonderful group of lawyers and non-lawyers here in Chicago and London and they are the most dedicated team I could hope to lead.

Before getting into things, how has your day-to-day changed in light of Covid-19?

Candidly, we’ve never been as busy as this year of Covid. My team and I all jumped right in working remotely in order to drive the critical priorities of Groupon. On a positive note, it saved me a 1-2 hour commute to the office five days a week. On a not so positive note, I truly miss the in-person interactions with my team and other Groupon employees. Zoom can only go so far in terms of personal connections.

Where did you grow up and how did you get into Law?

I grew up in Palos on the Southwest Side of Chicago before I went to college at Boston University and law school at Villanova. I got into law because of my amazing mom, who raised me as a single parent and went back to college and law school while I was growing up. She instilled in me the value of a good education and advanced degree while I was young and let me know that if law wasn’t my passion, the critical thinking skills I would gain from law school could be applied to any profession. Upon graduation, I worked as outside counsel in several firms before becoming a partner at Winston & Strawn in Chicago. I am honestly a very loyal person and didn’t envision leaving law firm life, but my Mom encouraged me to explore in-house roles. I was recruited to join Baxter Healthcare where I stayed for almost 12 years and found the old adage “Your mother is always right” to be apt — I loved being in-house counsel to a company because I was part of a team that helped drive business forward in a compliant and strategic manner. When I left Baxter, I joined Groupon and it was a great decision. We have a top notch, collaborative team and I am grateful for the friends I have made and experiences I have had to date.

What has been your proudest moment so far at Groupon?

In addition to driving some great outcomes in legal matters, I would have to say my proudest moment is seeing Groupon move in a more proactive and positive direction on Diversity, Inclusion and Equity. The day that we did the George Floyd forum where employees were able to share their feelings and thoughts about that tragedy (and many others) was so powerful. Not a lot of companies would do something so bold as to have an open forum like this. It was something that I will remember forever and made me very proud to work at Groupon. That work continues in so many different ways — in recruiting, talent development, minority merchant development and through our LISTEN, LEARN, SUPPORT and MOBILIZE forums that continue to drive programming that is meaningful to all our employees. It is a privilege to be the Executive Sponsor of the LEARN group, who has created a monthly newsletter and put on programming such as movie forums for “13th” and “Selma,” which educated employees on historical racism that continues to this day.

How are you staying connected with your team as we’re all working remote?

That is something that I really value and in the absence of live meetings together at the office, we have reverted to weekly meetings with our entire team on Zoom. In addition, we have tried to add “fun” events that are not work-related to keep our spirits up and just unwind. We’ve had several game nights, and Kevin McCormick on my team has introduced us to Jackbox.tv. We’re also doing a virtual escape room soon (I hope they won’t lock me in and all find their way out), and we’ve ordered dinner through Door Dash as a group to try and stay connected.

What is the best piece of advice you’ve ever been given?

When I had my second son, I was still working at Winston as outside counsel. I had a 2.5 year old (older son), and when I was on maternity leave, I had the typical mother “guilt” feelings of returning to work. I spoke with other women friends at Winston (“my tribe”) and one woman said to me: “You have to go back to work. You have two boys and they have to see a strong mother who is smart and independent in her own right. Whatever your boys may lose in terms of time with you while you are at work, they will gain from seeing you succeed in your own right.” It gave me the boost I needed to value my career and my children. Now that my boys are 18 and 16, they do value my work and my career. When I had a brief stint of not working between Baxter and Groupon, they told me: “Mom please don’t become one of those stay at home moms who is volunteering at the school and getting into everyone’s business and wearing Lululemons everyday. You are going to go back to work, aren’t you?!” Said like true teenagers, but I found it comforting that they saw the value in my work outside of the home.

How are you staying connected with your team as we’re all working remote?

That is something that I really value and in the absence of live meetings together at the office, we have reverted to weekly meetings with our entire team on Zoom. In addition, we have tried to add “fun” events that are not work-related to keep our spirits up and just unwind. We’ve had several game nights, and Kevin McCormick on my team has introduced us to Jackbox.tv. We’re also doing a virtual escape room soon (I hope they won’t lock me in and all find their way out), and we’ve ordered dinner through Door Dash as a group to try and stay connected.

How has your experience in other roles helped you in your current position?

As a leader of highly talented individuals, one experience that has really helped me is my work at WOMN LLC, which is a 12-month mentoring program in Chicago that helps women in law firms achieve professional and personal success through learning skills requisite to their roles as outside counsel. We focus on areas such as networking, branding, communication skills, and getting over career roadblocks (e.g., imposter syndrome, inequity, confidence building). To me, leading a team is all about ensuring they are positioned for current and future success, with both the hard-skills and soft-skills necessary to be a true leader. I work a lot with my team on the “soft-skills” and development, and leading WOMN LLC has made me more adept at this.

What’s the first career you dreamed of having as a kid?

My mother tells me that when I was two, I told her I wanted to be a “seeing eye dog!” That probably foreshadows the fact that I now have five dows and a cat thrown in for good measure. As I grew older, I wanted to be a teacher, and in a way, I think every good leader has the skills of a great teacher, as teaching is all about bringing out the best in every student.

Favorite pre-Covid activity you can’t wait to get back to?

For my birthday last year, my husband got me tickets to see the Guns n Roses and Bon Jovi. Both were cancelled and I cannot wait to go, as rescheduled. I miss almost any concert at Wrigley Field, Soldiers Field or Ravinia. Nothing like a great night of music with friends.

What do you love about your job?

I love the constant diversity of issues we face at Groupon, which enables us to strategically and creatively drive solutions to propel the business forward. But most of all, I love my team and the dedication they show to doing a great job day after day. They inspire me to be a strong leader and to help them develop and achieve their goals.

What is one non-work activity or hobby that you’re into? How did you get into it?

I am a huge sports fan, both watching and playing (e.g., hockey, football, March Madness basketball, tennis). My favorite is paddle tennis as it keeps me active during cold Chicago winters, but lately most of my time is spent watching my two sons play hockey. My older son plays for his high school’s varsity team, and my younger son plays for a club team. My older son hopes to play club hockey next year at college and my younger son is hoping to play professionally someday. Most of my free time the past fifteen years has been dedicated to driving to/from practices and watching their games. I find it to be so exciting to watch my boys do something they truly love.

Rapid Fire Questions

Favorite quote:

“There’s a special place in hell for women who don’t help each other out!” – Madeleine Albright

Eat in or dine out?

Dine out. I’m sick of cooking!

Morning person or night owl?

Consummate NIGHT OWL!

Favorite city you have visited?

The entire Amalfi Coast or Barcelona

#1 on your bucket list:

An African Safari with my family and friends


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