Four GCs and Their Path to the Legal Industry

For's GC 101 Webinar, our four panelists detail their first jobs and how they started in the legal industry.

Four GCs and Their Path to the Legal Industry had the distinct pleasure of hosting a General Counsel 101 Webinar with special guests, Samantha Villanueva-Meyer (Former Chief Compliance Officer at Enjoy Technology), Vineet Shahani (General COunsel and Head of Corporate Development at Chewie Labs), Shanti Ariker (Senior Vice President, General Counsel, Chief Privacy Officer & Corporate Secretary at Zendesk) and Mead Dixon (Head of Legal at Envoy). Pieter Gunst, CEO of, moderated the discussion.

For a portion of the discussion, we focused on the unique paths each of our panelists took to get to where they are in the legal industry today. Here are their stories:

Samantha Villanueva-Meyer Former Chief Compliance Officer at Enjoy Technology

“I was a classroom teacher [for my first job] and I was in education for about eight years. So, I didn't have law or law school or anything related to law on the books or the brain at all. I very much enjoyed my time, both as a classroom teacher and as an administrator, working eventually with Rice University out of Houston to do K12 curriculum development both in the state of Texas and nationally. I am from Texas, now residing in the Bay Area. I then chose to leave education to go to law school. And through my law school journey, [I] encountered a lot. Eventually, [I]  got into the business side and was hired by a very early stage startup called Enjoy Technology. And we were able to build a lot of things together over the past seven years. We went public and we have now completed an acquisition. So a lot of things I have learned through that process that we'll unpack today. But that's a little bit about me, my background and how I've made the jump from education to legal.”

Vineet Shahani General Counsel and Head of Corporate Development at Chewie Labs

"So my first job actually was a receptionist and a tour guide at the university I went to. And I've always told people that my dream job would be being a university president, being back in a college town. I went to law school and then I did BigLaw. So I was at a law firm for several years. That was how I transitioned to going in-house. I was at a small company at first out of the law firm and eventually got to Apple. Apple is what led me to Nest, the thermostats and smart home products. I was there early on, Nest was acquired by Google, so I moved into Google where I worked on the Google first-party hardware business. So that's pixel phones and the Nest business. We later acquired Fitbit and that was going great until I left early this year to move to this stealthy startup that Pieter referenced [Chewie Labs]. We are coming out next year with something that hopefully everybody will like. It's been great! I've been part of big legal departments, little legal departments and I look forward to talking about all that."

Shanti Ariker Senior Vice President, General Counsel, Chief Privacy Officer & Corporate Secretary at Zendesk

“My very first job was in high school and I helped to digitize somebody’s customer list [this person worked in the stamp-selling business], which is a fancy way of saying I did data entry. I did enter all of it into the database and then went from there. So that was my very first experience with digitizing a business. I started out working on Wall Street at a BigLaw firm and then moved back to California to another law firm and then went in-house. My very first position was at ETrade, which at the time was about 1,000 people - [they] were already public and had no legal department. I was the very first lawyer there, so they put me in the compliance department. I always say that I went in-house as a litigator and I came out as a commercial lawyer.

So I did a variety of different things at that company and [eventually] really gravitated towards transactional work. I became more of a transactional lawyer and then, you know, over the years did a variety of different things and ultimately landed at Salesforce in Canada. I was living in Toronto and worked on the commercial team, but eventually became the General Counsel of and Salesforce Foundation, where I then began working more on the corporate side of things. Eventually I made my way to Zendesk where I'm the General Counsel today of what is currently still a public company, although we do plan on going private when our transaction closes.”

Mead Dixon Head of Legal at Envoy

I'll go with the first job I had post-college and I'll loop a couple together because I had to work two jobs. One was working at a tea room in Philadelphia, making and serving tea (basically a barista, but without the coffee). The rest of my time I spent at a gourmet food and cheese company doing web design, writing and some design work. After law school, I started off with the clerkship at the bankruptcy court in a district of Nevada. I stuck around there for a couple of years and then moved into a very small commercial litigation firm. I think that was a big influence on how I think about risk now. It was also where I learned that I very much do not want to do litigation, so I really gobbled up any sort of transactional bits of work I could find while I was there. In a way, [I] served as an ‘outside/inside counsel’ for a few of our clients. From there, [I] moved on to a global open source enterprise middleware company called WSO2. We were very distributed [with 95%] of my team in Sri Lanka. I was the only attorney handling the US work, [which was] very commercial-oriented. And then I made my move to Envoy; started out as a contractor here and then moved full-time just a few months ago. That's how I ended up where I am now.

All of our panelists bring a unique perspective to their careers and, as panelist Mead Dixon noted during the webinar, “I took an unusual route to where I am now. If I can become Head of Legal that way, there's clearly no defined path to being Head or GC.”

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