From personalized handcrafted jewelry to a hand-knitted version of U.S. Supreme Court Justice Ruth Bader Ginsburg, Etsy has something for everyone.

And it falls to Jill Simeone, the e-commerce site's general counsel and corporate secretary since January 2017, to oversee the Brooklyn, New York-based Etsy's legal department, which includes 24 people working on legal, compliance, advocacy and policy matters.

In a wide-ranging interview this week, Simeone spoke with Corporate Counsel about everything from her unusual route to the top to what it's like to navigate the ever-changing world of e-commerce and internet law. The conversation has been edited for length and clarity.

Corporate Counsel: How did you go from being a prosecutor in the New York County District Attorney's Office to where you are now?

Jill Simeone: I was in the DA's office as a sex crimes prosecutor for five years, after which I realized I didn't want to be there forever, so I really had to think about how to leap into a different box.

So I applied for a Fulbright Scholarship in international business and law. I went to Mexico and did graduate work at a university there and was also embedded in a company, where they liked me and were willing to trust me. I found a mentor there who helped me convert into a corporate lawyer, and I was with that company for about a dozen years.

What really carried me through was that at the DA's office I learned to be a strategic thinker. I had become a great negotiator; I was good at multitasking; I had street smarts; I was able to solve problems; and I was able to reach resolutions through influence. Those are the skills that made me successful in corporate law and allowed me to transition my career.

A lot of people want their career ladder to be just straight vertical and, if you do that, you're not building for a rich career, and you're also not taking in the feedback of how the world changes. When I graduated from law school, the internet was brand new, so it's not like this job could have been a dream of mine at the time.

What is it like working in e-commerce law?

There are a lot of business law jobs out there, and they're not always that exciting. I love the analogy I've heard about Ginger Rogers: She does the same dance as Fred Astaire but backward and in heels.

I think e-commerce is similar. It's just like regular business law, except we're doing 17 other things. The shop never closes; we're in the cloud; we're in 100 jurisdictions; we have complex cyber and privacy issues. I think the dance of being a tech lawyer in e-commerce is part of the excitement and the challenge, and I think we're dealing with a really fun area of the law.

What are some of those challenges?

A lot of issues and areas in e-commerce are in flux. Sometimes I say that if you become a maritime lawyer, the law was settled 100 years ago so you just need to be really good at maritime law.

But if you're an internet lawyer, the law hasn't been settled yet. You're making analogies, and you're making judgments based on what's been decided before. But maybe the issue before you hasn't been presented, so we're dealing with a lot of really cutting-edge legal issues.

One of those cutting-edge legal issues was recently addressed by the U.S. Supreme Court in its Wayfair decision. How has Etsy been dealing with the consequences of the ruling?

We submitted an amicus brief in the Wayfair case when it was before the Supreme Court. It is a decision that affects remote sellers in jurisdictions, so it is a decision that really affects our sellers.

One of the things that was interesting about this case is that it was presented as a situation where there was an easy technology solution, a button you could push that would fix this. But it's really complicated for our sellers because they sell a lot of unique and unusual things that don't really track to a [number assigned to a product for stock-keeping purposes]  and that don't really line up with a specific definition. What could be athletic shoes in one jurisdiction is a sneaker in another or a hiking boot in another, and they all have different tax rates, so it's a challenge for our sellers.

We're working with them, and we're helping them solve those questions. We've also been fighting for some de minimis exemptions so small sellers don't have the same tax compliance burden that the big mega-business sellers do.

Etsy says it strives to create an environment where “you can bring your whole self to work,” and strongly emphasizes diversity and inclusion in the workplace. How do you implement those values in your department?

I am very interested in recruiting a really diverse team of players on my legal team. I want some people who are junior; I want some people who are more seasoned; and I want people who have come from different backgrounds.

The focus when I got here is to not have an inbox legal department. I want a legal department that is really excited about being embedded in the business and about coming up with new solutions to problems that maybe haven't been answered before. And in order to do that, you need people who are excited by change and by grappling with complex legal issues.

And then we talk about those issues a lot. We'll sit around a table, and with a diverse team, there could be three or four different approaches to solving a problem, and that's where you really get the rich discussion and the best solutions.

As a tech-forward company, is there an increasing reliance on technology in the legal department?

I actually think that the more complex regulations get, the more we rely on lawyers. Again, in tech law, it's not as if there's a place where there's an answer for these issues.

Right now we're launching an updated contract management system, but a really important part of this project is that we didn't want it to be just a contract management system. We took a lifecycle approach to our relationships with third parties and a broader approach to third-party oversight, and that really ties together issues of information security, privacy, vendor management, compliance and quality of relationships with our vendors. With that, we understand that the payments are happening on time, and we are able to onboard and offboard our vendors in a uniform manner. 

The legal team really took the lead on building a cross-functional team to tackle this project, and we're well on the path to doing that.