In-House Counsel at a Software Company

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From LawHub, this is I Am The Law, a podcast where we talk with lawyers about their jobs to shed light on how they fit into the larger legal ecosystem. In this episode, Kyle McEntee interviews an in-house lawyer at a software company amidst transitioning from the legal side of the company to the business side in HR.

Kyle McEntee:

We're joined today by Zoe Sharp, a 2003 graduate of Stanford Law School. Zoe is currently VP Deputy General Counsel and interim head of Talent & Culture at Optoro, a software company that helps retailers process, manage, and sell returned and excess inventory. But like so many lawyers who go in-house and transition to the business side of a company, she started out at a large firm, Williams & Connolly, which is to say the least, highly selective. Can you tell us a little bit about how you ended up going down the Big Law path?

Zoe Sharp:

I went to law school really as a path of least resistance. I was a junior in college. I was a typical English and history major and I liked taking tests, so the LSAT didn't seem very intimidating, and went straight to law school from there. With hindsight, I think it was a great path for me, but I don't think I put especially careful thought into it upfront. When I applied to law school I had visions of working in public defenders' offices, and legal aid, and doing all the good that I thought I would do when I applied.

But like 80% of my classmates, I realized that what you do when you leave law school is, you get a law firm job so you can start paying back your loans and also so you can get trained. That's what led me down the firm path. Also, having worked at firms a couple of summers, I really enjoyed the work, so was excited to get in the door at Williams & Connolly once I finished clerking.

Kyle McEntee:

Yeah, so I'm sure you had a lot of options post-clerkship. What was it about Williams & Connolly that made it particularly attractive?

Zoe Sharp:

I actually ended up summering at four law firms. All of them were excellent firms. But of those four firms, Williams & Connolly was the one where I thought I was going to get the most responsibility, I was going to get to work closely with these legendary lawyers that I had interacted with over the summer, and the people I respected and consulted all kind of pointed me in that direction. It didn't feel like a hard choice at the time.

Kyle McEntee:

This firm in particular kind of has an interesting structure, so there's no corporate practice. Is that right?

Zoe Sharp:

Well, there's one guy, one or two guys, that support things happening on the litigation side. But no, there isn't a focused big transactional practice.

Kyle McEntee:

And also they kind of have that old-school bullpen.

Zoe Sharp:

That's right. It's evolved probably since I was there, so if you go on their website now they're our group. But it was not that way when I was there. People were known for certain things. The lawyer who had been general counsel of the FDA was certainly known for food and drug practice, but everyone thought that they had the ability to pick up anything and to do it, and the associates didn't specialize.

Kyle McEntee:

When you have a bullpen, often that means there's no formal assignment system. How did you see that affecting how work was distributed?

Zoe Sharp:

Having a free-for-all system definitely favors the most aggressive, which is actually a skill that maybe is valued in the litigation environment. It definitely creates repeat customers. So if you get in early with somebody you wanted to work with and you do a good job, you're going to continue to get those opportunities. But it can be challenging for a junior attorney that lacks confidence, connections, or clarity about what you want to do. So if you just complete what's assigned to you and you think you're meeting the expectations, you're not going to thrive. I do think that firms are evolving in how they think about this, and firms are taking new and important steps to create opportunity, and distribute work equitably, and promote different types of work styles.

Kyle McEntee:

I would imagine it also kind of produces more of a generalist mentality, or maybe that's actually the cause of why an assignment system would be less formalized. Was that something that you liked about going to Williams & Connolly?

Zoe Sharp:

Yeah. I mean I will say, and I love looking back on it, that I did at least one or more of probably a dozen different kinds of cases. I did healthcare. I did intellectual property. I did malpractice defense, both medical and for accountants. Having the chance to do all the different fields is great because then you can say you've done something on your resume and as you move forward. But the flip side of that coin is, you don't build a deep specialty in a subject area.

Kyle McEntee:

Now, is that what ultimately kind of pushed you to go in-house with Sallie Mae?

Zoe Sharp:

Yeah, I did. I thought that if I continued to practice law in a generalist way, I wouldn't have my own brand that I could trade on and thrive as a individual lawyer versus a piece of the firm.

Kyle McEntee:

I have to ask, how much did work-life balance factor in to moving in-house? I think that's a common assumption people have that the in-house attorney has a significantly better work-life balance.

Zoe Sharp:

I didn't have a terrible work-life balance, and maybe that was not typical. But I like to chug and bill my ... I mean each week was heavy, but I didn't have massive spikes and then months off or days I didn't sleep. I think I never pulled an all-nighter in my firm days. So I'm proud of that, and I don't ... In-house life, it doesn't mean you're not working really almost the same hours. I will say my first weekend at Sallie Mae it was very odd and uncomfortable to come home and have nothing to look at on my BlackBerry at the time, and nobody was writing me over the weekend. I said to my now husband, boyfriend at the time like, "What do people do on the weekend?" I really didn't know, and I had to develop some coping mechanisms, which was a good thing.

Kyle McEntee:

That's pretty funny. Let's fast-forward a few years. You left a second financial services company to be Deputy General Counsel for Optoro. So this really was a move away from specialization and back to a more general practice. Was that a conscious choice or was this about something different?

Zoe Sharp:

The thing that really drew me over to Optoro was just the chance to have a lot of fun. In the smaller environment I have the opportunity to really get involved with everything and also to really work closely with my business clients. And that's just been so fun. At a bigger organization in a legal function where you have maybe 30 colleagues, the 30 lawyers you work with those are your colleagues and your environment. You're not sitting next to the business decision makers throughout your workday typically.

Kyle McEntee:

I do want to clarify for listeners, by business clients you don't mean the external customers, you mean the people who are making those business decisions internally for the company.

Zoe Sharp:

Yeah, I think of my business clients as our CEO and our other internal leaders.

Kyle McEntee:

How large is the legal team, including non-lawyers?

Zoe Sharp:

It's me and the other guy. We have a general counsel. I'm the deputy general counsel, and from time to time we've had interns.

Kyle McEntee:

Oh, wow. And are there any paralegals, or legal assistants, or compliance officers?

Zoe Sharp:

Those are all me also. So unlike my first day at the law firm, I had a secretary who would be mad if I tried to scan my own documents or file them, today I can scan all my own documents, file them, write my own letters, print them out, file them. I have a lot more autonomy to meet the needs to get my day-to-day work done than I did earlier in my career.

Kyle McEntee:

So now that you've been there nearly three years, I want to talk a little bit about the legal work that you've been focused on. Can you give us kind of a high-level overview of those different types of things you've worked on?

Zoe Sharp:

Our business, which you described at the outset, we have a software that helps retailers process returned and excess inventory. So we're a tech company. To support that software business I've been involved in licensing, marketing, privacy work, security. And then we also sell that returned and excess inventory, so we also are an e-commerce business. So for that I've been involved in e-commerce, compliance, even product safety, intellectual property infringement issues, and then, as in any business, some employment issues. And then more recently, our warehouse was devastated by a tornado, since then have been involved some in insurance issues and other things relating to that. So really a little bit of everything.

Kyle McEntee:

When you don't know something, where are you going to figure out what you don't know?

Zoe Sharp:

There are a couple of things I do. And unlike in my past job, the first thing I do is not usually call outside counsel. We try to be pretty self-sufficient. I value the Association of Corporate Counsel where I can ask questions of peers through the industry group. I have another industry group for retail lawyers where I also can ask questions of peers. I have a sort of short list of closer friends that I can ask an offline question if I want to make sure it's not going on the record or getting spread around. And there's a, it's a Westlaw product, a database called Practical Law that has tons of information that we use.

Kyle McEntee:

Do you feel like this is kind of a trend for in-house counsel to be more self-reliant and rely on these, I don't want to say generalized resources, but resources that are not particularized to your situation?

Zoe Sharp:

It depends on the business, the size of the business, the risk for us. We haven't had a lot of litigation. I'm sure that if we had lots of lawsuits I'd be telling you something different. But for basic sort of figure out what the law is in 50 states and make sure you're complying with it, I think that's changed a lot because of the ability to look that up and crowdsource it. Also, I think that the advice I give us based on my own research, I have more confidence in.

One of the challenges we have with certain law firms, and I'm not talking about our current law firm partners specifically in any way, but often law firms give you a very conservative answer because they don't need to calibrate the business risk because legal advice after all is just advice. And the business can say, "Okay, I understand what you're saying about the risk." But if it's not illegal, if it's assessment, business will want that calibrated and will not want a hard yes/no answer in a more gray situation.

Kyle McEntee:

I want to dig a little bit into some of these areas a bit more deeply, and I want to start with privacy. Let's say there's a ransomware attack. How do you think through what your response is going to be, and how do you balance all the competing interests in your efforts to minimize the damage?

Zoe Sharp:

I would say first, and this is something I've enjoyed doing since I've joined Optoro, you set up a really strong framework. You figure out upfront who will be responsible for what if something bad should happen. We call it an incident. We have an incident response plan. So you know who's on the line, who needs to be notified, who do you call, who's your lawyer, who's your insurance contact? And we have all that. So if whatever event, be it ransomware, breach, something else like that happens, you sort of start running the play that you planned. And you try to notify all the impacted parties within the necessary timeframes, decide whether to involve law enforcement, just kind of go down the checklist, and you take the steps you planned to take.

Kyle McEntee:

Right. So because you're so lean, you have to not only think about the planning but also the execution, and then I'd assume the review afterwards.

Zoe Sharp:

Yep, the postmortem.

Kyle McEntee:

I want to talk a little bit about the HR policies that you developed given your new role as the interim head of essentially HR. What's the role of a lawyer in that process?

Zoe Sharp:

The role of a lawyer is to partner closely with the HR team and think through what policies or documentation may be needed. Most things were in place before I joined. So the agreement the employees sign when they join the company in which they agree not to share trade secrets and things like that was already in place. Our employee handbook was already in place.

But just looking at what we have, and what's out there, and what's best practice, and we identified opportunities to add some policies and some approaches. So we added a code of conduct. I think that was mostly a legal-driven effort, but really needed a lot of input from Talent & Culture to make sure that the document we put together reflected how people were living. Otherwise, we'd just be in violation of our own document immediately.

Kyle McEntee:

Right, and people would get mad I'm sure.

Zoe Sharp:

Yeah. One of the policy efforts that was most complex and challenging was the document retention and preservation approach. Because people have very different practices, and very different expectations, and very different filing systems. So aligning a business around that was a really interesting project.

Kyle McEntee:

Can you talk about that project a little bit? Kind of what went into it and how you thought about it.

Zoe Sharp:

Sure. When I joined the company we basically saved emails and other things. But the business was so new that saving everything forever was still practical and possible. And we're very paperless, so it wasn't like we had a storage unit with 30,000 boxes somewhere. But when I joined I thought, "Our clients have things they put in contracts of how long they expect us to keep things. We have statutory, and other, and privacy obligations that make you not want to keep everything without thinking through where it is and how long you're going to keep it." So kind of looking at all the statutory requirements and our practices, we tried to figure out the best way to approach that for the business.

Kyle McEntee:

So what do the challenges look like in terms of getting company buy-in from those individuals? How do you persuade people that this is the path that they should take, or once it's adopted, that they must take?

Zoe Sharp:

I think the biggest challenge for us was Gmail, because we're a Gmail system. Gmail has an incredible search function, and really almost makes filing obsolete because you can search your own emails for everything forever. I recently saw a study that actually people who didn't file anything and searched email were more successful finding it than people who had filed it. But the problem with Gmail is when people leave. Because if they leave, then you don't have access to anything they had. Versus if they had filed it in Google Drive or elsewhere, their successors would have access to it. For that it was really trying to explain the need for that change in practice and explain the benefits of changing the practice.

Kyle McEntee:

I guess now that's even more closely aligned with your role at the company because now you have that additional hat of running HR, which is a non-legal role. How has the balance of your work shifted since taking this new role on?

Zoe Sharp:

The balance has shifted dramatically. Especially recently with us working remotely now, and I'm spending probably 80% of my time on HR things. And the way that that shifted my approach, when I was in a legal role I was thinking about risk. I was saying, "That's not a good idea because we might get sued." Those were the types of concerns that I was balancing. And now that I'm in the HR role I'm really trying to put people first and think, "Here's the impact on employees and this is the reaction you might get," and change the perspective that I'm advocating.

Kyle McEntee:

Often when we think about lawyer competence we think about a toolkit of skills and knowledge. How do you feel that that toolkit that you developed over law school and your many legal jobs, how has that translated for you in this relatively new role?

Zoe Sharp:

I think the legal skills are very translatable to many things. But in the HR role I think of it the most when I am talking to a departing employee. We call these exit interviews. Or when I'm talking to someone who's upset and I'm trying to understand why. And those conversations can often feel a lot like I'm drawing on the skills I developed in taking depositions. You're trying to figure out what the other person knows, and you're trying to get them to share it with you so that you can take action based on the information, which is exactly what you're doing in a deposition.

It draws on empathy, it draws on sort of scenario imagining. Right? You have to sort of think through what they might have in their mind and figure out how to get it. But the other is understanding how things can play out. So being a litigator you see all these different human scenarios of disgruntled employees, or businesses gone wrong, or malpractice, and I think understanding how where you are tomorrow might be different than where you are today is a universally valuable experience.

Kyle McEntee:

Key to that seems to be some elements of flexibility. Maybe that's just putting it in a different way. You've talked already about two pretty major business challenges where I think your flexibility maybe has helped you serve and protect your company's interests. First, the tornado that took out that warehouse, and now dealing with the pandemic. Can you talk a little bit about these business challenges and what your role has been in them as they come up, I don't want to say completely out of nowhere, but more or less this is not something you plan for a year out.

Zoe Sharp:

Yeah, I think flexibility is, as you said, incredibly crucial. You have to immediately, and I mean in less than a half hour take off the hat of what you came in planning to do that day, set it aside completely, ask yourself what you have to do to get through the next day or week for the business, and start executing on something new. And I think it's been interesting to go through this experience in a startup environment because the business is so nimble. It was quite amazing to see the business be able to have a new warehouse up in a week and then manage the second crisis of needing to suddenly disband the physical workforce in D.C. and go completely remote.

We were able to do that in one day. And when you make that decision you have to think through, "Okay, what do we need to tell people? We need to tell people to take monitors home. They might not have thought of that. We need to tell people whether or not they can come in next week if they forgot something." So just kind of thinking through how you best protect the business, the employees, and also keep going forward without causing panic definitely required flexibility.

Kyle McEntee:

I think it's kind of funny you mentioned the monitors because I was at Best Buy shopping for monitors about four hours after my state announced the stay-at-home order, and they were already completely gone. And a lot of people were just completely out of luck because they didn't think about this, didn't have someone thinking about it for them, and then could not get into their office to get that monitor.

Zoe Sharp:

Yeah. Well you know, as much as I was thinking about it for other people, and I did have a monitor at home, I did not have the kind of setup where you would want to sit eight to 10 hours a day. But it hadn't occurred to me, even in that moment as I was planning for it for our entire workforce, it just hadn't occurred to me that I would be sitting at that setup for eight to 10 hours a day for now five weeks.

Kyle McEntee:

Right, and who knows how much longer.

Zoe Sharp:

Yeah.

Kyle McEntee:

So the last question I want to talk about goes to your Deputy GC role. Which is, how do you see that role evolving for you as a result of the pandemic?

Zoe Sharp:

This is such a challenging time for businesses and especially for retailers who are our primary clients. I don't think all of that is known yet. We're trying to pivot as quickly as we can to provide value to them, but what issues or challenges may lie ahead I'm not completely sure on the legal side.

Kyle McEntee:

And I guess it'll be that toolkit of yours that will help you figure it out as you go and do the best job you can.

Zoe Sharp:

Yeah. I mean I think we're fortunate that I'm not anticipating some new type of litigation. We're not, I don't think, vulnerable to that. Some businesses are and have already been sued. The future's a little bit unknown. We'll try to be as flexible as we can and react as we see things coming.

Kyle McEntee:

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