I recently had the opportunity to sit down with Gusto Legal Lead Liza Kostinskaya . A year and a half ago, she made the leap from a leading Silicon Valley law firm, Fenwick & West LLP, to a rapidly growing midsize company. She discussed the reason for this transition and provided advice for attorneys considering a similar move.

After a successful career in Big Law, you decided to make the bold decision to accept an in-house role at a tech startup. What fueled the change?

LizaI really enjoyed working for Fenwick, but when my favorite client reached out about an in-house position, I accepted, because I wanted to help build a business that I believed in and help them scale from the ground up. I had the chance to experience the “Fenwick Dream” of working closely with a client through its early stages and then being asked to come on board as their first legal hire. I didn’t hesitate when deciding to make the jump, and since then, I’ve had the opportunity to build out the in-house legal role from scratch. I have zero regrets about doing so – coming to Gusto has been an incredible experience.

Aside from the professional opportunity, the decision was easy because I loved that Gusto has such strong values. The people are kind and generous and really care about the company and their colleagues. The opening was too amazing to pass up.

You mentioned that you got to build a team from scratch. When you interviewed Gusto’s second legal hire, what did you look for in that person?

There are so many talented attorneys who are tightly specialized in one area of law. This is great in many situations, but for a tech startup like Gusto, we needed a jack-of-all-trades. We needed somebody that was thoughtful and adaptable because there is so much variety in the work. Two legal projects rarely look the same.

I hired a coworker from my previous law firm. She’s skilled at corporate law but also talented at evaluating issues, assessing potential paths and being really smart about selecting the best course of action.

You noted being a jack-of-all-trades is very important. How did your previous experience at a big law firm prepare you for this role?

At a large law firm, you develop the skill of handling a high volume of work at the same time, and every detail matters. Working at a large law firm taught me how to be both fast and accurate. I’d say the most important skill I developed during my time at Fenwick, and that has served me well at Gusto, is judgment – recognizing when an issue is important, when something is worth holding firm on, and when you might be able to let something go. The analysis and risk tolerance might be much different at a firm vs. being in-house, but I rely on my law firm training every day.

Of course, a major difference from being at a law firm is the variety of the work I see every day. I might be handling employment law at breakfast, reviewing a contract at lunch and studying new laws in the evening. Never a dull moment! No day is the same. 

When making this transition there is a learning curve. Key to overcoming this curve was having really great mentors. For anyone making a similar career move, I would highly recommend building a strong network of mentors with in-house counsel experience. I often bounce ideas and concepts off my friends and contacts at other companies, because we are often dealing with the same kinds of issues. Finding friends and mentors at other companies (especially those with a few more years under their belt) has been invaluable to me.

Gusto office with stack of wood

If you were to give advice to another attorney looking at this path, what would you say? Is there anybody who shouldn’t travel this path?

Serving as in-house counsel for a tech startup might not be the right path if you struggle with ambiguity. Most of the time you won’t know the right answer 100 percent, and you must be OK with that.

At a big law firm, you’re often focused on perfection and mitigating all legal risk. But in-house, you’re making decisions about what’s right for the business. Not everything is black-and-white; there are many gray areas. So you have to be prepared to work in those gray areas, but also be ready to stand firm on issues that you as a lawyer are specially equipped to analyze and be aware of. 

Also, if you like to be an expert in one particular practice area, this isn’t really for you. There are many different areas of law to learn, so you’re never really an expert in one area. But if you enjoy blazing a trail, learning continuously and working at a really fast pace, going in house is a great path.

Give us the inside scoop on the hours? Is working in-house less rigorous than a big law firm?

The amount of hours is similar, and the stress is about the same, yet the type of stress is different. I don’t have to work weekends if I don’t want to, but there is always more I could do. I’m always worried that something more can be done. For example, what happens if we don’t hold this training session and somebody makes a mistake?

I’ve learned to balance risks with what can realistically get done in a day.

But overall, leading Legal at Gusto is amazing work. I love the variety, and I’m not planning to transition back to Big Law anytime soon.

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About the author

Courtney Cregan

Courtney Cregan

Courtney Cregan is head of content and PR at UpCounsel. She has more than five years of experience working at AmLaw 100 law firms. Courtney earned a bachelor's degree in women and politics from Trinity College in Hartford, Conn.

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