In conversation: Samantha Von Hoene, Chief Legal Officer, Enjoy Technology, Inc

Having joined Enjoy straight from law school as it’s sole legal counsel, Von Hoene set about building both a team and her own skillset. Now CLO, she reflects on that unusual journey.

GC: Could you tell me a little bit about your path to Law?

Samantha Von Hoene (SVH): Before I went to law school, I was a teacher. I had originally studied engineering, and realised that I had a lot of ability to affect people’s lives as I taught science and math. I worked on that specifically for females; getting involved in STEM education fields is really important. From there I started working with foster youth, and, based on that work, I decided that I would have a larger platform to change the world if I went into Law. When I went to law school, I realised that education reform was something I wanted to do as a pro bono career, but that I wanted to focus on professional growth opportunities and ways to change other industries. So that’s why, in law school, I changed to study and learn corporate and business facing law. That’s also why I chose not to go the traditional law firm route – I really wanted to be involved with people, lives, and working with cross-functional teams, and so that’s why I ended up going in-house.

GC: How did you go from coming into Enjoy straight out of law school to becoming the general counsel?

SVH: That was a big step. While the original plan with Enjoy was for me to work under a GC, that plan quickly evolved into one where I would come in as solo counsel for the company. I took a chance on the small start-up (then only in San Francisco and New York) and more importantly, Enjoy trusted and took a chance on me as a very new lawyer. The company has grown substantially during my time here, now serving partners like AT&T, Google, Sonos, and British Telecoms and operating in more than 50 US Markets and the UK.

From my first days at Enjoy, I did enough of both the tactical and strategic work that they were really able to see the value of having someone who knows the business intimately to grow into that general counsel role, which is what I did. After a few years, I took over as general counsel, and then later transformed into chief legal officer, owning key areas of risk, including cybersecurity/infosec, compliance, trust and safety and legal, in October 2018.

GC: It must have been quite a reward after all the hard work?

SVH: It has been a really incredible journey. I remember how scary and risky it was to go through the entire bar study period in the US without knowing for sure what my job would be, but when I got that phone call from Enjoy, I knew I had such a good family of people there cheering for me. Many Enjoy employees had become friends of mine that knew me and my previous part-time work with the company, so when I got that phone call that said ‘Yep, we want you to come here and start,’ it was pretty awesome.

GC: You’ve taken quite a non-traditional route, to ignore the entire law firm side of it and come straight in-house as a corporate lawyer, rather than from private practice. How did the experience you had compare to that of your peers who might have gone the law firm route first?

SVH: Everyone in law school encourages you to do your five-to-six years at a law firm, to get your experience and then go in-house, because then you’ll be ‘ready’ to go in-house. For me, it was a little different. I immediately realised that I wanted to do something non-traditional; I had a purpose in that I wanted to help change an industry, I wanted to work with teams and to work with great people – I didn’t want to be in a windowless office all day stuck working on meaningless paperwork. So I was very purposeful about the opportunities I took when I was at law school, and those opportunities eventually led me to Enjoy.

When you get in-house, you actually realise pretty quickly that most experience you might have had as a lawyer in a law firm would very quickly evaporate, because in-house is very different. Your audience is predominately key business stakeholders, not firm partners. Business leaders don’t want to read a four-paragraph analysis on an intense legal issue. They want to hear yes or no, the risk associated with the yes and the risk associated with the no, and they want to figure out how their business is going to operate best given the risk analysis you’ve provided.

For me, it was the right choice to go in-house right away because of that experience, and also because of the relationships I’ve been able to build along the way. I think that if I had gone to a law firm immediately, I would have had a lot less exposure early on. Given my current situation, I’ve now had exposure to most large major telcos in the world, in addition to the biggest innovative companies around, getting to talk and liaise with them, to craft and negotiate potential deals with them, and build our internal structures to support such great companies. Its pretty incredible to see what a company like Enjoy can do when they’ve got a strategic visionary leader like Ron and people in place who want to grow to make it happen.

GC: Is there anything you feel you may have missed out on by not working at a law firm first?

SVH: When you choose one path you have by definition not chosen another path and, in my case, I had chosen not to go the law firm route. I think what you miss out on is the mentorship and the ability to have another lawyer right across the hall who can give you real-time advice on that very specific issue that you just worked on. I didn’t have that for a long time at Enjoy. I had to rely on my mentor network, I had to rely on other business-owners in the office saying, ‘Yeah, that’s a good idea’, or ‘No, I don’t know why we would do that’, and go with my gut a lot. So it made me stronger in that way. But yes, I think that at a law firm you gain a lot of mentorship opportunities really quickly.

But I would say that the same situation can happen in-house; the issue is that a lot of general counsels have not prioritised it. I am prioritizing it. I offer intern and extern programmes, so people can come in when they’re in law school and get three or four months under their belt with me and my team, so they can understand what it means to work in-house, what it means to work on cross-functional issues as a lawyer, and they can get that real critical balance of experience between legal analysis and business acumen. Once they have that, they’ll be invaluable to any business they want to go into. We’ve seen that time and time again with all my past interns. In order to continue this reach and opportunity for law students, I am helping other general counsels set up intern/ extern programs as well.

GC: What was the time period from when you first got the offer to getting the offer to become general counsel?

SVH: About a year and a half. I knew when they gave me the job offer that no one else was coming in. When they gave me the job offer, they said, ‘We think we’ll make it, we’ve got outside counsel, you’ve got plenty of help, you’ll make it work.’ And it was at that point that I said, ‘Ok, I already know you guys, I’m committed, I’m in, let’s see what happens!’

You come in, you start working and you realise, oh wow, trial by fire, I’ve got to learn this, every day is a new day, every hour is a new challenge – and you learn to swim by being thrown in the pool, essentially. You’ve got to sink or swim. Luckily, at Enjoy, we’ve got an amazing team to say, ‘We’re going to help you swim, we’re going to make you get there, don’t worry.’ But also there’s a lot of pressure when you’re up against the AT&Ts and the other large, major corporations of the world – they’ve got 20+ person legal teams and you’re a year into your role of lawyer and you’re trying to negotiate a big deal or argue some nuanced regulation with them. That’s hard. But I made it work, and once I did that, I was able to move forward with all the key business stakeholders at Enjoy to really help them to understand: this is what I do, this is how I do it, and this is the support I need from you. That’s when I really started to see some major traction, and the jump-start from my transition from sole legal counsel to general counsel to my current role as CLO.

GC: Was there a gap between them saying ‘We believe in you’ and then, on a personal level, you saying ‘I can actually do this’? A lot of the time, believing in yourself can be the difficult part.

SVH: Oh that’s the hardest part, 100%. You can win over the team relatively quickly – you can show them a few great examples of what you do and how you do it and everybody loves you. The hardest part is getting over, as Michelle Obama and others have put it, the imposter syndrome. ‘What am I doing, I’m not supposed to be here, this is not me.’ And that will forever be something that plagues any young lawyer, it will be forever something that plagues young female lawyers. But the truth is that once you prove it to yourself a few times, you start getting comfortable with ‘I can do this and I can do it well’. It doesn’t mean you’re perfect. I make mistakes all the time. But I have a good enough relationship with the people I work with every single day that when I make a mistake, they are my safety net, because they help me figure out what the next step is. It’s really uplifting to have that safety net when you’re young in your career, and making very large-scale moves up the ladder quickly.

GC: Can you tell me about your first time advising Ron Johnson – how was that?

SVH: You know, working closely with Ron, a retail legend, for many that is a terrifying moment because a lot of people have idolised him since his time at Apple, and for good reason. He is an amazing visionary who understands the retail business better than anyone most people have ever met in their lifetime. But I was not in the retail business before going to law school, so for me, I knew him from the outside, as someone who had great ideas and amazing insight. And when I started working with him closely I realised, ‘Oh my gosh, he gets it, and he’s setting a unique and innovative path for this whole company.’

It’s pretty amazing to be able to present and to work with Ron on a daily basis. He is incredibly strategic and also very tactical. He rolls up his sleeves and gets it done. Scary is not the right word. I think it’s empowering to work with someone like Ron. It keeps you professionally engaged, because you either need to continue growing or continue getting better or be on your way out. There’s no room for stagnation when you’re working at a company like Enjoy, or when you’re working for a boss like Ron Jonson. You need to constantly be evolving, constantly thinking about how you are going to approach the next business issue in a way that makes sense for all the risk that is fundamental to the issue, and you need to figure it out. And you’ve got to get it done, at the end of the day. There’s a little bit of scare tactic in there, but more than anything it’s the light of the fire that keeps us all going.

GC: These days, do you see yourself as a lawyer first or as a business person with legal training?

SVH: I’m probably a more of a business person with legal training at this point. I think that that’s a hard answer, because everyone who goes through three years of law school and the bar exam wants to tell you, ‘I’m a lawyer first and I wear my lawyer hat’. But the best in-house lawyers have a really firm and fundamental understanding of the business. So, for better or for worse, I think I am a business-minded lawyer who uses my legal hat but leads with my business strategy and what I perceive as the best path to take given the legal risk within the business.

A year ago, I feel like I would not have said that. But as your business grows, as you scale, when I think about the questions that Ron, our CEO, is asking me, what are the questions that our leadership team is faced with every day, it’s legal analysis and work that goes into those questions but it’s the business mindset that ultimately helps you to make the decision.