Sivan Whiteley, General Counsel and Corporate Secretary, Square (Photo: Courtesy photo)

Under Sivan Whiteley's leadership as general counsel and corporate secretary, Square, Inc. became one of only seven companies to obtain a New York cryptocurrency trading license, allowing residents to buy and sell bitcoin with Square's Cash App.

In 50 words or less, how far has the tech industry gone toward tackling its gender gap since you started practicing?

Not far enough.

Name a lawyer whose work you admire and why?

Sally Yates recently came to speak to our team. Her honesty is powerful. She also brings a common-sense approach. One of our takeaways from her talk was how important it is, as lawyers, to not overwhelm with information, but rather use judgment to distill down what's necessary in order to present a clear argument or proposal.

What's the best part about working in the tech sector?

The tech industry is dynamic by nature. So is its legal environment. Constant learning and iterating is requisite. As in-house counsel, we are able to closely partner with product teams from the start. Getting in on the ground floor empowers us to weigh in on those early discussions and impact product development, which is really exciting.

What's the biggest challenge?

Tech moves quickly, and as innovators we find there's not always a natural regulatory fit or precedent for what we are doing, so we work in partnership with regulators to help educate them on the direction of the industry.

What piece of advice do you give to lawyers considering a career in tech law?

Provide advice from an empathetic mindset by first thinking about how an idea or proposal provides value or improves a customer experience. Turn to the legal challenges and hurdles only after you've spent a minute considering the situation from that perspective.

What's one way technology has made your life easier?

Given [that] our employees are working from geographically diverse areas, video conference meetings have changed the game and allowed for a more distributed workforce. Workday flexibility, remote working and collaboration across the globe are the working modes of the future and VC meetings enable that change.

One way it's made your life more difficult?

Need to make intentional space for downtime.

Name an important opportunity you got early in your career and what you did with it.

Very early in my career, I was given the opportunity to argue motions in big cases before I felt I was ready. I learned that some of the best—and fastest—education comes from being uncomfortable and just jumping in.

What's the best piece of career advice anyone ever gave you?

When making a tough call, “don't be the only one in the boat.”

No. 1 survival tip in a work crisis:

Listening is a non-negotiable first step. Spend time gathering information and understanding the issue before you go into problem-solving mode.

What's one way you've had to change your thinking toward practicing law to succeed in-house at a technology company?

I stopped thinking about the legal barriers first. There's always a reason not to do something. Start with what's best for the customer, then figure out how to make it happen within the confines of the law. That's innovation.

What's one area of technology that you're most excited about and why?

Machine learning. For example, in an anti-money laundering (compliance) context, machine learning is allowing us to accurately, quickly and efficiently identify our customers and keep them safe.