Ep 188 | Cheree McAlpine | Chief Legal Officer at Zoom is a Leader in Dynamic World of Legal Tech

Thank you. I mean, the story is similar to what you just described. I wanted to join a company that has an impact on people's lives, and Zoom above any other company taught us... I just sent my cousin over to their house and I said, 'Just tell them to press that button, and they can see me and my brother.' I'm not gonna say that Zoom saved their lives, but it certainly had an impact on their mental health.

I am from rural Alabama. I grew up in a really tiny town in Alabama. It was so rural, Benny, that at one point my address was Rural Route One, an indication of how rural it was. It's a small town on the Alabama-Georgia border. But it's also a town that I continue to go back to very often. I have family there, I have strong ties to the community. I think people have perceptions about what it means to be in a rural community, but for me it was a great childhood and a great experience growing up. I was raised by a single mother, and she raised two children quite well in rural Alabama.

Yeah, so you're right. There was no connection to lawyers, which was very common to a lot of people in rural communities. The only connection was TV, probably. Not just rural communities, but in a lot of communities. But I'm a corporate lawyer, so even on TV they were more litigators, trial lawyers who at the end of 50 minutes solved all the problems. That was kind of my perception of a lawyer, nothing like the reality of being a lawyer. So I went to undergraduate at the University of Alabama, majored in English literature. I'm from this rural community. Four years passed by, I'm graduating, and 'Oh no, what am I going to do with an English literature major in rural Alabama?' But I'd also been an RA, and so I applied to a lot of universities to be an RD. I ended up in Boston as an RD, and I thought at that time, 'Okay, I'm gonna have a career in higher ed. I'll be like a dean of students or something.' At the time, universities were having a lot of legal issues, so I thought, 'I'm going to have a career in higher ed. I'll go to law school because then I don't have to go and get a PhD and do all that work. My advanced degree will be a law degree.' So that was my first inkling about going to law school. Then I'm in law school and I realized some of the stuff is pretty interesting, some of it a little more fascinating. But even at that time, I thought of law as litigation.

I asked him for references. 'Who do you know? I think I want to be a litigator.' I ended up moving to California, applying for jobs in California, and got a job at Wilson Sonsini. Their corporate practice was very busy and they had just started their San Francisco office, and they didn't have a litigation practice. They had patent litigation, but I clearly didn't know anything about that. So I ended up getting thrown into a corporate practice, and I thought, 'Oh, this is going to be a disaster. I don't know a corporate lawyer.'

One day, a partner walked by my office, stopped, came back, looked at my name on the door, looked at me, and said, 'Hey, you're new here, aren't you?' I said yes. He said, 'What are you working on?' I said, 'I'm literally just sitting down at my desk.' He said, 'Come with me.' I got up from my desk and followed him. I ended up following him for two different law firms, and that began my career. He was like, 'Follow me to my meeting.' I'm sitting in this meeting, he's talking to a client, it's an M&A deal. He was a securities lawyer. Coming out of that, at some point in the meeting I realized, 'Oh, I probably should be a corporate lawyer.' It was a very interesting place. I never thought I'd be a tech lawyer, I never thought I'd be a corporate lawyer, and I've only ever been a tech lawyer and a corporate lawyer, and I have loved it.

Yes. And then I eventually went in-house. I wanted to be closer to the business. That's what I loved. I loved the partnership that happens when you do that. At a law firm, there's a lot of different clients, but I really loved rolling up my sleeves, learning the business. How does my legal advocacy advance the business? I tell you, it is that love of the business that brought me here in March.

Yeah, you know what? It was in those classes that first year, meeting my first lawyer and starting to really develop an understanding of what lawyers do. I still wasn't quite convinced that I would be a lawyer. I thought this would supplement other things. I always tell lawyers and law students today, you don't have to be a lawyer to be in law school. A law degree can help you with many other things. So I think that was my frame of mind that first year. It was only in about the second half of the second year that I started to take a legal career more seriously.

I have to manage litigation, but I let the litigators do the litigating. I do the managing of the litigators who are doing the litigating, because it would be a disaster for me to try a case with my corporate background.

I think timing plays a big role, and it's also about seizing opportunities when they are placed in front of you, being bold about that, and believing in yourself. As a lawyer, the types of projects I was working on during the dot-com period were really transforming the technology industry. I worked with partners who had a lot of confidence in my skill, probably more confidence than I had in my own skill at the beginning. But they really had a lot of confidence, and I learned a lot. It set that course for where I am today.

First, you have to want to be there. If that's where you want to be, it's not... I once had a CEO who said, 'Every day is not a high-five day.' So if you're looking for non-stop high-five days, please don't run in the direction of the C-suite. Run in a different direction. What it takes is someone who first of all wants to be there, who understands the business, who's willing to roll up their sleeves and operationalize the legal aspects of the job. If I needed someone to just tell me the law, just tell me the risk, then outside counsel are great for that. But what makes an in-house lawyer special, and what makes an in-house lawyer at the C-suite level special, is the ability to help mitigate risk for the company but also to help drive business success. You can't have one without the other. If you want to sit in the C-suite, you need to understand that role of mitigating risk, but you also need to understand what it means to put on the business hat to try to drive business.

Yeah, our legal department is over 100 people globally. That includes lawyers, contract managers, paralegals.

I would say be strategic about your career. Be very thoughtful about where it is you want to go. Talk to people who've gotten there, find out how they got there, create your own map, your own plan on how you're going to get there. I think the biggest problem that sometimes young lawyers or young professionals make is that they think, 'I'll sit here and I'm just going to work super hard, I'm just going to do it, and my hard work will be recognized, and I will have the success that I want to have.' You need more than that. You need to know how to be a self-advocate, you need to know how to build relationships, you need to know how to solve problems, and you need to know how to demonstrate value. Doing some of those things, or most often, 'I'm just going to sit here and let my hard work speak for itself.' It speaks for itself, and people may recognize the hard work that you're doing, but that's only a piece of it. You've got to be able to demonstrate that you can do other parts as well.

All the time. Wow, a lot of issues or matters of first impression. There's not a lot of specific laws around AI, not a lot of specific guidelines to help us chart our path. So in a lot of respects, we're charting our own path with other companies to make sure that we're doing it in a responsible way. I'll give you an example. One of the biggest things that we talk about at Zoom is the responsible use of data. Making sure we're doing it responsibly and ethically, but also that we're doing it legally and mindfully.

Zoom does not do that. We're very deliberate about doing that, and we're very outspoken about it.

Yeah, I think some of the biggest challenges that we had, which Zoom had and other companies had, was the workforce. How do you deploy the workforce during a pandemic in a way that keeps people safe, that's responsible, but also keeps the doors open and enables our ability to provide products to our customers? Zoom had that challenge, the company I was at during the pandemic had that challenge, and companies around the world had the challenge of keeping workers safe. In this post-pandemic environment, it's been about how do we return to work. What are not just legal considerations but also business considerations for most companies?

Yeah, for someone who was an English literature major, not an engineer, not a biologist, not a chemist, does not have a science background, I have loved every minute of being a tech lawyer. What has been interesting about it for me is that I've been doing this for a very long time, so I've seen the different iterations of technology. I was there for the dot-com phase, I was there for the internet phase, I was there for the social media phase, and now I get to be here for the AI phase. It's just fascinating to see the creation and what we're capable of as humans, pushing technologies in ways that hopefully will make our lives better.

People ask me this all the time. I think it's going to make our jobs better. There is something so unique and necessary about how risk is balanced by lawyers. It's nuanced, and I don't think machine learning yet has really understood that nuance and that situational awareness that lawyers bring. I think AI will help us with contract management, with negotiation and execution of commercial agreements, with entity management around the world, and outside counsel management. All of those things, we are starting to see AI in these areas, and I think we will continue to see AI. I'm less concerned about the threat to the profession, but I do think if there's any threat, it's for those who are not willing to embrace technologies and find ways to use it to make our lives better.