Jack Dorsey's Inner Circle at Square

Many CEOs of billion-dollar public companies have more than enough to keep their hands full, but for Jack Dorsey, it's astounding he doesn’t need extra hands at all.

Dorsey co-founded Twitter in 2006 with Noah Glass, Biz Stone and Evan Williams and currently leads the company as its chief executive officer. Three years later, Dorsey co-launched Square: a financial service and digital payments company designed to help smaller businesses with credit card processing and point of sale transactions.

Square is the second company that Dorsey leads as CEO, and is also the second company he’s led to a billion-dollar valuation. Founded alongside Jim McKelvey, Square rivals other U.S. fintechs like Stripe and PayPal.

Take a look at how Square stacks up its popular products like Tidal and CashApp throughout its succinct org chart.

As the figurehead of the company, Dorsey is extremely well-known throughout the tech and entrepreneurial world. His inner circle at Square consists of eight C-suite executives, and exactly half of the company leaders are women.

One of the most powerful women at the company is Amrita Ahuja, Chief Financial Officer and Treasurer, who is second-in-command to Dorsey.

Ahuja has only been with the company for three years, and before she accepted the CFO job she was working as CFO at Blizzard Entertainment, a division of Activision Blizzard. Ahuja has also held various leadership roles at Fox Networks Group, the Walt Disney Company and Morgan Stanley.

Square’s current org chart also reflects its new initiative to transition from just a payment processing platform to a broad financial services company. Exemplifying this is Seller Lead Alyssa Henry, who rose through the ranks on the infrastructure team to get to her C-suite role at Square.

Henry started at the company in 2014 and was responsible for Square’s software and hardware infrastructure. She now heads the company’s seller business unit, which focuses on pretty much every operational corner of Square: engineering, marketing, data science, partnerships and the seller-facing product suite, just to name a few.

Henry’s background is in product and computer science. She worked for over a decade on various teams at Microsoft and was the VP of Amazon Web Services (AWS) Storage Services before joining the team at Square.

One of the biggest projects Square has developed has been its successful CashApp service. Brian Grassadonia co-created the mobile payment and money transfer service that rivals Venmo in 2013 and currently serves as team lead. Since its launch, it has quickly risen to become one of the biggest revenue generators for the company thanks to a viral and influencer-driven marketing strategy. It brought in $849 million in 2020 and accounts for two-thirds of Square’s $65 billion market valuation.

Grassadonia now leads the CashApp team within Square as EVP and General Manager. He started at Square in September 2010 as the first Product Manager and later launched the first Growth team at the company. He previously worked as Manager of Corporate Development at Slide before it was acquired by Google in August 2010.

In May, Square further broadened its horizons by acquiring an 80% ownership over rapper Shawn “Jay-Z” Carter’s streaming platform, Tidal. The move placed Carter on Square’s official board, and now industry veteran and Apple alum Jesse Dorogusker oversees the music service at Square, along with the Hardware team.

Dorogusker has been with Square since 2011, joining after eight years at Apple where he worked as Director of Engineering for Apple’s iPhone, iPad and iPod accessories business.

Perhaps its least-established new product is TBD, Square’s cryptocurrency and decentralized finance business unit. Mike Brock officially directs this effort. Brock has held a number of leadership positions at CashApp and was responsible for setting up Square Crypto, an open source, independent initiative focused on a more accessible global financial system for the internet. Prior to Square, he was a principal software engineer and project lead at Red Hat.

On the legal front, Sivan Whiteley oversees all legal, regulatory, public policy & communications, compliance, and security operations as General Counsel. A longtime leader of Square’s legal team, she previously held positions at Better Place, eBay and Bingham McCutchen.

Rounding out the executive team is Helena Christianson, the People Team Lead. Christianson is an experienced human resources leader, and has a background working in HR leadership at Apple on the product and engineering teams. She’s responsible for employee policies and scaling at Square, a big job considering the company has over 3,000 employees distributed across the country after it’s permanent work-from-home policy was announced in 2020.