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Sivan Whiteley is the General Counsel of fintech payments company Square. She is a prime example of a lawyer who manages numerous challenging responsibilities. As the head of Square’s legal department, she is faced with many complex legal, regulatory, and business problems. Whiteley also navigates the demands of running a large legal department of a tech company. Despite its size, the company retains many characteristics of a startup culture.

Founded in 2009 by Jack Dorsey, Square is one of the largest fintech companies in the world. The original inspiration for Square came after Dorsey and his co-founder observed a frustrated small business owner. The owner was unable to process a sale because he lacked the technology to accept credit card payments. The company’s first product was the Square Reader, a credit card processing tool that connects to a mobile device’s audio jack. Square’s point-of-sale systems provide seamless merchant processing for both small and large businesses.

Some of Square’s major competitors today include PayPal, Shopify, and Clover. Dorsey also serves as a CEO of Twitter, a company he founded in 2006.

Square Breaks the Mold with Two Consecutive Female GCs

Sivan attended University of California, San Diego, where she majored in political science and economics as an undergraduate student. She then went onto Harvard Law School. Whiteley began her career in a law firm, and her first in-house legal role was at eBay. She then moved to the role of Associate General Counsel at Better Place, a startup that develops battery charging services for electric cars.

Square’s previous General Counsel, Hillary Smith, also graduated from Harvard Law School. When Smith joined Square in 2016, she received an $8 million compensation package. Smith stepped down in 2018, but during time as Square’s General Counsel, Smith played a pivotal role in launching bitcoin trading on Cash App, a mobile payment service developed by Square in 2013. Bitcoin transactions have been a huge profit generator for Square. In the second quarter of 2021, Square earned $55 million in profit from bitcoin transactions. In the first quarter of 2021, Square generated $75 million from processing bitcoin transactions.

How Square’s Legal Department Does Things Differently

Unlike many other companies, at Square the legal department plays a key role in decision making and shaping the course of company strategy. Whiteley works closely with other executive officers, including Chief Executive Officer Jack Dorsey and Chief Financial Officer Amrita Ahuja.

“Jack named us a long time ago ‘the counsel team’ and it’s not an empty name, he believes the function serves as advisers, people who are in the room from the beginning or the moment someone has an idea,” Whiteley stated. When you’re moving money, everything’s regulated, so it’s an exciting place to be as a lawyer because you’re not just in the room because you’re forced to be in the room, or because you’re a check box along the way: they want you there.”

Under her leadership, Square’s legal department has focused on improving the automation of certain legal processes. For example, Whiteley hopes to use artificial intelligence technology to automate the drafting of non-disclosure agreements, waivers, and other relatively standardized contracts.

Square Expands into Other Industries

Based in San Francisco, Square became a public company listed on the New York Stock Exchange in 2015. It currently has a market capitalization of around $120 billion. Today, Square’s point-of-sale software is available in several countries worldwide and can accept payments in different currencies, including the Australian dollar and Japanese Yen.

While Square is best known for its peer-to-peer payments, the company is making strides into investing and banking services. Square’s recently announced acquisition of Afterpay Limited, a pioneering “buy now, pay later” platform. Once Square brings Afterpay on board with Cash App, customers who purchase by installments can manage their accounts in the app.

Although it is primarily a financial services company, Square has diversified into other business areas. Square acquired Caviar, a food delivery company, in 2014. Square later sold Caviar to DoorDash in 2018 for $410 million. It has also diversified into the music industry. In March 2021, Square reached a deal to acquire a majority stake in Tidal, the music streaming company owned by Jay-Z.

A GC Who Also Oversees Diversity Initiatives

Thus, as the General Counsel of Square, Whiteley is responsible for overseeing a broad range of business industries. She must stay on top of the latest legal, business, and regulatory developments impacting the diverse areas of Square’s business.

In addition to her involvement in Square’s legal and business functions, she is also involved in diversity initiatives. “What I’ve found, and it’s really distributing, is people bring to pitches a diverse group, but it’s not who’s actually working on your matters. We’re doing an audit and looking at how many hours each person billed,” Whiteley commented. “Even in meetings, if you have a diverse group of folks coming over to meet, when you pay attention to who does the talking, it’s still the same.”