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Jonathan Leiken
Chief Legal Officer & Secretary, Dollar Tree Inc

Episode #5 In-House Counsel Chronicles with Jonathan Leiken Executive V.P., Chief Legal Officer &...

🎥 Jun 17, 2025 📺 Shawna Rosner ⏱ 24m 👁 17 views
In this episode of In-House Counsel Chronicles, host Shawna Rosner interviews Jonathan Leiken, Executive Vice President, Chief Legal Officer & Secretary of Dollar Tree, Inc. He's an experienced general counsel with a rich background in both private practice and in-house roles. Jonathan emphasizes the importance of being curious and open-hearted in one's legal career. He shares how General Counsels play a crucial role in navigating complex legal challenges for public companies. He also discusses the impact of global events, such as a global pandemic and the war in Ukraine, on legal responsibili...
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Transcript (35 segments)
S
Shaa Rosner0:00
I'm Shaa Rosner, your host of In-House Council Chronicles. Jonathan Leiken is my guest today. Jonathan graduated with a BA from Brandeis University and his JD from the University of Pennsylvania Carey School of Law. Jonathan has worked in big law as well as with government and in-house, chief legal officer with two public companies, both Diebold Nixdorf for almost 10 years and currently with Dollar Tree stores. Somehow Jonathan has also managed to carve out time to teach law at Case Western University School of Law and of course at the Ohio State University, which I'll talk about later in the podcast. I'm so excited to have you join the podcast today. Welcome.
J
Jonathan Leiken0:45
Great to be here, Sha.
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Shaa Rosner0:45
Thanks so much. So start obviously, as I've shared, you have quite an impressive legal career thus far. When you were in law school, did you imagine your career would take the path that it has?
J
Jonathan Leiken0:48
No, absolutely not. And I tell my law students actually that when I was sitting in their chair, if somebody had told me just how many jobs I would have in my career, I would have been terrified. But I also tell them that our profession is like a river, and maybe uniquely so, and if you are curious and open-hearted, that it can lead you to all kinds of amazing places. And then I describe to them the very stops that I've had that you just chronicled and say, you know, if you let that current push you where it wants to and you're curious, you're in for the ride of your life.
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Shaa Rosner1:41
Yeah, that is true. It's good advice. And I often talk to attorneys and what I do are looking to go in-house or make a move within house. They want to be a part of the business of the company or part of the C-suite. So I'd like you to tell us about what it means to be Executive Vice President and Secretary along with Chief Legal Officer title, which is the title I think you hold now. Was that a title also that you were hired for or did you grow into that title?
J
Jonathan Leiken2:09
So I became a GC through my work as an outside lawyer, actually. I was doing legal work for — I was a partner at Jones Day and represented companies in civil litigation and big government investigations. And one of my longtime clients was Diebold, and Diebold, this is all public, was I represented them in two large government investigations by the DOJ and SEC. And at the end of the second one, which was a Foreign Corrupt Practices Act investigation, the company was about to enter a three-year DOJ monitorship, and I was counseling the board and the leadership about getting ready to get through that monitorship and to build a world-class compliance program. And they turned to me, to my surprise, and said, 'Well, why don't you come and lead that?' And it was not something I had even really thought about, but it was an incredible opportunity. And when I got into the job, when I originally took the job, honestly I thought maybe I'd do this for a few years, help the company get through this monitorship, and then go back to private practice, which I loved. But found once I was in the role that I just love being a GC and I love working on an in-house legal team. And over time, I've even begun to teach about it, as we'll talk about later. But I happen to think this is where the action is in this profession. It's where the most interesting work is, and it's also a way to really meaningfully contribute to something bigger than any one of us. And so I love it.
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Shaa Rosner3:46
Well, I'm sure lucky to have you in this capacity. You've been practicing in-house now for about 12 years, and both in-house positions that you've held were for public companies. Was that a conscious decision of yours to work for public companies? I know you explained a little bit about how you got to Diebold, but what else can you share there?
J
Jonathan Leiken4:09
Yeah, I mean, not certainly not conscious or purposeful, I would say. Given my background as a federal prosecutor and then a white-collar criminal defense lawyer and lawyer to large companies, the kinds of problems that I've solved in my career have tended to gravitate toward public companies, which uniquely have obligations about reporting and disclosure, dealing with the regulatory landscape of a public company that I'm uniquely suited to help. And I love public company work, but it wasn't something that I chose. And this is the advice that I give to law students: you know, oftentimes the position chooses you based on the skills that you have, the ways that you can solve problems. So I would say I've become a public company GC by trade because it's something I very much enjoy and I think that I have unique skills to do that kind of work.
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Shaa Rosner5:10
Yeah, I appreciate that because I don't see a whole lot of people that start their career in private practice in white collar particularly going in-house.
J
Jonathan Leiken5:10
It's funny that you say that because I think there is an increasing trend of a number of us who were prosecutors and then have found their way into being public company GCs. And there's actually a growing number of us in larger companies. And I think that the way that we look at work and the world is uniquely helpful. We understand the perspective that the government has in looking at companies in the most serious type of reviews, investigations, charges. We understand what it means to run an effective compliance program, especially in a lot of complex environments. But we also understand from this side that the world is not black and white, it's often very gray, and have an ability to translate that back to our former colleagues in the government, which comes up quite often, especially for public companies. That makes a lot of sense. So you're seeing more of that and attributed because of the reasons you just kind of mentioned.
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Shaa Rosner6:17
That makes a lot of sense. So you're seeing more of that and attributed because of the reasons you just kind of mentioned.
J
Jonathan Leiken6:17
Yeah, I think a lot of former prosecutors are finding their way into in-house roles, into GC roles. And as I said, I think increasingly it's just where the action is in our profession. It's a place, as you say, where you can be part of something that you're growing as part of a team instead of being — and while I loved my work as an outside lawyer, I always did feel like a mercenary. You come in, you get to know the people and the business and the issues, and then if you do a good job, it ends and you have to say goodbye and start all over again. And that's the exact moment when you feel like, 'Boy, I've really started to get to know this business and these people. I'd love to stick around and help it grow and succeed when we're not just managing a crisis.' So I think a lot of in-house lawyers feel that way. But the other thing I've learned, Shaa, and I'm sure in your profession you see this every day, in-house lawyers, there's just something really special about them. They're just a uniquely caring and dedicated group of people, people that are real problem solvers. They walk in the shoes of their business partners. They have amazing stories for how they landed in these roles that each one is unique and kind of their own journey on a river. But I really come to love in-house lawyers as a group. And so being around them and caring for them and being a servant leader of in-house teams has also been just a tremendous surprise and joy for me in my career.
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Shaa Rosner7:53
Yeah, I do talk to attorneys every single day, whether they already are in-house attorneys or so many want to make that move. And I agree, there's such a great bunch. And what you shared about the dedication and why people are attracted to it makes so much sense to me. While you were general counsel at Diebold, a global technology company, I understand the company had business operations in over 100 countries. That's right. So what was it like supervising legal issues in so many places around the world?
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Jonathan Leiken8:23
It was amazing. It was truly amazing. So everything that I said about in-house lawyers is also true of international in-house lawyers. And at Diebold, I supervised a team of lawyers from countries all over the world, all across Europe: Germany, the UK, France, Spain, Italy, all across Asia. And when you work with people who are lawyers but who grew up in different legal systems, you get insight into how a different country thinks about the same kind of issues that we do as American lawyers. And what I found is that even though the rules are different everywhere — for instance, every country has its own rules about the attorney-client privilege, for instance, and when it applies and if it applies in certain situations — but all of us lawyers speak a common language about right and wrong and kind of this essential meaning of what is just, and also using the law as a tool to both problem-solve and teach our business colleagues. And that has just been an amazing part of my life, honestly, learning how different legal systems treat these same issues, and then meeting and working with lawyers who have kind of the same core values that we do as American lawyers, and then figuring out how to translate into solving business problems. It was a great, great joy, but also a tremendous challenge because places are so very different. And we'll talk about this later, but you know, with the events that occurred over the period of time that I was GC at Diebold, over 10 years, the world changed so dramatically in so many ways, and we had to navigate those issues together.
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Shaa Rosner10:13
Yeah, I want to talk about that a little bit. During your tenure at Diebold, the world entered a global pandemic that was in 2020, and then the war in Ukraine began in 2022. You were still there. How did these global events create issues that landed on your desk as a general counsel?
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Jonathan Leiken10:34
Yeah, and this is something I teach about in my class about being a GC. You know, we are — I mean, the world changes every day, and as a general counsel, you truly are a generalist where you're the company's primary problem solver on novel issues. So in 2020, the GCs of the world for global companies, many of us became the de facto chief medical officers of our companies and had to figure out how to navigate a global health crisis while also caring for our employees, making sure that they were safe, but also making sure that they had paychecks, that our business could continue in a safe way. So for Diebold, out of the 22,000 employees, we had a huge chunk of them are service technicians. Diebold is the largest manufacturer in the world of ATMs, and our service technicians fix and maintain those ATMs. They were needed desperately during the pandemic because people wanted access to their cash. So the question was how to keep our technicians safe with the right equipment, the right medical protections, but also how to keep them on the road. So we had to navigate the legal regimes of every country where we do business in order to have us designated as an essential business, but also to make sure that we were doing that safely. So that went on for two years while we managed that health crisis. And then in 2022, the war in Ukraine broke out, and Diebold had a significant business both in Ukraine, in Kyiv, and also in Russia. And so we had to navigate in Ukraine getting our employees to safety. We had more than 100 employees that we had to figure out how to get to the countryside just so that they and their families could be safe and out of harm's way from daily bombings. And then in Russia, as the West left Russia when sanctions were imposed, we had to figure out how to both exit the country but also care for over 100 employees, many of whom had been with us for a very long time. And navigating Russian law while also making sure we complied with the sanctions, but also being human beings for people that were our colleagues, presented just a host of issues. And while it was incredibly hard and the pandemic still wasn't over at that point, it was also incredibly rewarding because we found ways for people that just kind of warmed the heart. And the kind of humanity that we saw from not only our own colleagues but friends and customers and colleagues around the world was incredible.
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Shaa Rosner13:15
Wow, those are things I never really thought about, like how the pandemic or the war in Ukraine would impact the general counsel. But it totally makes sense. You know what you're saying. Well, letting that sink in a little bit because that's a lot.
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Jonathan Leiken13:31
Well, and that's one of the many reasons why being in-house is so rewarding and often thrilling, because the issues that come up can be so new and something that you never thought you would have to deal with, but the company needs solutions right then and there. The place you call — you know, who you going to call? It's the general counsel's office. And then you put together a team of really smart in-house lawyers who work on other things, and you sit in a room and say, 'What are we going to do about this? How can we solve this?' And you figure it out. It was amazing.
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Shaa Rosner14:07
Yeah, what an experience for sure. You know, you mentioned one of the words you mentioned was humanity. And I think of you as such a humanitarian because despite such a very busy career in law at a major global law firm and as GC of two public companies, you've always found time for civic and charitable work. You've served as the president of Legal Aid Society locally and the Cleveland Bar Association in Cleveland. Why are civic issues and causes so important to you as a lawyer?
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Jonathan Leiken14:36
I think that they're central to the profession. You know, ours is a helping profession and a teaching profession. And I think if lawyers don't dedicate some mind share in their lives and careers to giving back to the community, I think there's something missing, and I think we're not kind of fully ourselves in the job. But I also have found that companies, law firms really benefit when their lawyers are out in the community doing good. It reminds the company that every good company has a mission to help the world in some way through its business. And if you have a legal team, you want those lawyers out in the world helping through the lens of their professional skills. It's just what we do. And I learned this from mentors that I worked for over the years, from my parents. My dad is a lawyer and always found time for civic work. But it's also just incredibly rewarding and fun to work with and around other lawyers that are doing great things and giving back. So it's definitely a big part of who I am, and I think it's a big part of who we are as lawyers.
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Shaa Rosner15:51
Yeah, I think it's great. We've really been fortunate to have you in our community. And I feel that way about giving back. It's something that was kind of embedded in me from my parents, like you said. And it does make sense. I think lawyers do have that inherently. And I do hear a lot of law firms and companies that want their attorneys to give back to the community, to be really a part of the community. So I'm glad to hear that you've been able to take advantage of that and are a role model, I'm sure, for so many others in the profession.
J
Jonathan Leiken16:23
Well, that's the other thing about this job is that lawyers are teachers. In all my teaching that I've done over the years, I always talk about that there's a Supreme Court case called Upjohn versus United States, and I always teach it early in the semester, and it's all about the corporate attorney-client privilege. But in that case, Justice Rehnquist talks about in-house lawyers and says it's the in-house lawyers that are the ones who teach the company how to follow the law. And I always use that as just an example of the fact that yes, we lawyers are advocates, and we're problem solvers, and we're writers, and we're oralists, but at our core, I think the very best of what we are is to teach. And that includes teaching young lawyers, new lawyers about giving back.
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Shaa Rosner17:10
Yeah, and I know that you are a teacher. As you shared, you told me that you teach a course at the Ohio State University School of Law called 'To Be a GC: The Role of the Modern General Counsel.' Tell us a little bit about that. I went to law school, I know that wasn't a course that was taught then.
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Jonathan Leiken17:30
Yeah, it's something that increasingly law schools across the country are starting to teach, just about what it means to be a GC. And students are really interested in this because, as you say, I think a lot of lawyers are catching on that being in-house is where really interesting things happen and good things happen in careers. And law students are figuring this out too. A lot of great law schools across the country are starting to teach this. I got the idea during the pandemic, actually. I was home, I was working from home, and I was just thinking about all the amazing things about my job and thought, 'Boy, this would make a great law school class.' So I started researching it. I ended up contacting — I found out that at Columbia Law School they were teaching a similar class to what I was imagining. I reached out to the adjunct professor there, who at the time was the general counsel of Brooks Brothers, and asked her if I could see her syllabus. She willingly shared it. I concocted my own. And then since then, the course has really exploded across the country. And I've shared my syllabus with the general counsel of the University of Michigan, who started a class at that law school. And there's so many great GCs who are willing to come in and meet with the students. So we've had GCs of some of the biggest, most interesting companies in the world come and talk to our law students about this job and what it means. And it's been just a total joy.
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Shaa Rosner19:00
I love that. And you also teach at Case Western Reserve University as well.
J
Jonathan Leiken19:07
I do. So when I left the US Attorney's Office in Manhattan and moved back to Ohio to practice at Jones Day, I started a class at Case Western Reserve Law School called 'White Collar Crime: Prosecution and Defense.' And that is really all about my work as a federal prosecutor and also my work as a criminal defense lawyer. And I've been teaching that class amazingly for 20 years. I can't even believe that it's been that long. And for years I've said it's probably time to hang it up and just put it away. And then every year the issues get more and more interesting. And I have so many friends and colleagues who work in that space that we've had incredible guest speakers come and talk to the students as well. So at some point I'll probably wind that down, but I do love teaching it.
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Shaa Rosner19:53
Yeah, I could tell you're a natural teacher. Those are some great courses that I'm sure have impacted the students over the years, and they won't want you to stop. I'm sure it's a lot of fun. If you could travel back in time and give yourself advice as an attorney who just passed the bar exam, what would it be?
J
Jonathan Leiken20:14
Honestly, I would say what I say to my students, which is just take the ride and don't worry so much, which is I think what advice we can all give our younger selves. You know, we spend so much time fretting about especially little things that we don't often take time to enjoy the ride. But I'd give the same advice I give to young lawyers, which is let that river take you where it wants to go, and be curious, be open-hearted, and know that there's really interesting things just around the corner that you just can't see. And yeah, that's exactly what I would say. But the big advice would be not to worry so much because we all do that too much, right?
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Shaa Rosner20:59
Yeah, and as you said, your path took a course that you didn't imagine, so I think that's really great advice. Is there any different advice that you would have for our listeners who are aspiring to go in-house or make a move within in-house roles?
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Jonathan Leiken21:15
So if you're an outside lawyer working at a firm and you're curious about this, I would say to you definitely pursue it. It's a terrific career, and you'll be surrounded by great lawyers in the in-house community. I'd also say find a business that you believe in and where you think that the mission matters. Every business has a mission, but the best businesses have a mission that kind of speaks to who you are and your own values. And I've been really fortunate. You know, Diebold was a technology company that served financial institutions and retailers and provided systems and software and services to those companies in a way that solved huge problems around the world. And now as general counsel at Dollar Tree, one of the world's largest retailers, we serve communities. There's 16,000 stores, 200,000 employees, and we help communities get what they need and want at low prices. But having to navigate a massive regulatory landscape — we sell over-the-counter drugs, we sell medical devices, we sell food — and making sure that all of that is done in a safe and compliant and efficient way is a true mission that needs real problem solving. So I would say to lawyers thinking about this area, find a business that speaks to you and where you would enjoy kind of rolling up your sleeves and really figuring out how to solve that business's problems. It's a lot of fun.
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Shaa Rosner22:54
Great advice, great advice. I did want to close today by talking a little bit more about Dollar Tree. You mentioned its size, over 200,000 employees. What's it like being the general counsel of such a large company?
J
Jonathan Leiken23:09
It's a huge responsibility and something that I take very seriously. My colleagues on our legal team take incredibly seriously, and it calls for real servant leadership, which is how I think about what leaders are. And that means that when you go to work every day, your job is to make the lives and careers of the people on the team better. And when you work at a place like Dollar Tree, you have to think about how to do that at a massive scale. And that means you need to have the right processes, the right ideas, the right systems, and the right kind of chain of problem solving in order to care for all of those people. It also means that anytime you have a solution for something, like if you want to create a training on a particular type of problem, you have to really think about how to get that out at scale and make sure that it's accessible to people in 16,000 different places all over the continent. So it's a huge responsibility, but also something that I care about very deeply and feel grateful that I have the chance to impact so many lives.
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Shaa Rosner24:18
I'm so glad you do. I think that's a great place to end. I've really enjoyed our conversation today. I think our listeners will get so much out of our discussion and really appreciate you being a guest.
J
Jonathan Leiken24:30
Yeah, likewise, Shauna, thanks so much for having me.
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Shaa Rosner24:35
Thank you, thanks, take care.