Ajmere Dale Is Accountable for Supporting Innovation at Square

Ajmere Dale builds financial foundations meant to last in one of the most fast-paced and disruptive environments: Silicon Valley

Like most other people in his profession, Ajmere Dale did not grow up dreaming of becoming an accountant. “Like most kids, I wanted to be an astronaut,” he says with a laugh.

Ajmere Dale Square
Ajmere Dale, SquarePhoto: Terence Bordon

Accounting may not have been Dale’s first calling, but his knack for numbers has led him to the top of his field as chief accounting officer at Square Inc.—and his enduring passion for exploring new frontiers has earned him a reputation as a trusted business partner to some of the most visionary companies of our time.

An engineer by training, Dale began his career at Jaguar Cars in the days before the automotive legend was acquired by the Ford Motor Company. But in 1989, he decided to switch tracks, quickly completing a combined business and engineering master’s degree at the Imperial College, London University and then securing a chartered accountancy trainee position at Ernst & Young (EY).

“I wanted to get the best training possible at a global firm known for being very much people-first,” Dale says of his seven years with EY. “And it worked out well because I had the opportunity to travel and get overseas experience, including experience in the United States.’

“And once I landed here in Silicon Valley,” he continues, “I just knew that this was the right environment for me. There was so much opportunity, so much diversity in what was happening—it was a prime example of the American Dream in terms of how people were following their dreams of innovation and trying to make a difference.”

And for the past twenty years, Dale has been working with some of the brightest minds that Silicon Valley has to offer, from software and biotech pioneers to the leaders of Tesla subsidiary SolarCity Corporation.

“If our product teams are not innovating, the rest of us wouldn’t be here. So, at the end of the day, we have to support that innovation.”

“All the companies I’ve worked for have tried to do something different—they’ve been disruptors, explored new ground, addressed new markets,” Dale reflects. “And with its IPO, SolarCity went through something that is very unique. There are a lot of challenges and risks involved with an IPO and timing can be everything, so not a lot of companies get the opportunity or the right conditions to go through it.

“We managed to get it done,” he continues, “and it really was a testament to the whole team. You face a lot of abstract problems with an IPO, but you don’t have the luxury of taking time to think them through. You have to build and drive the car at the same time.”

But a willingness to explore new markets and opportunities isn’t the only thing that attracts Dale to a company. He looks for organizations that make an impact, whether that means developing tools for cancer detection, helping to solve the global warming crisis, “or empowering individuals who don’t have appropriate access to the financial system, which is what we try to do here at Square.”

A leading financial services and mobile payment company best known for the square-shaped chip readers that allow secure payments to be made any time, any place, Square Inc. is really an “incubator of ideas,” Dale says. And it’s up to him and his accounting team to help support those ideas.

“We don’t bury our mistakes here—we bring them to life and celebrate them as opportunities to grow.”

“As I learned at SolarCity, you have to be a strong voice of principle if you ever think that the company’s growth is crossing lines that are unacceptable and your starting to operate outside of predefined boundaries,” he notes. “But if our product teams are not innovating, the rest of us wouldn’t be here. So, at the end of the day, we have to support that innovation and, as we grow the team, ensure that we’re hiring other people with a growth mind-set.”

Square as a whole has experienced exponential growth since undergoing its own IPO in 2015, Dale says, but is still nimble enough to launch new products very quickly. Accordingly, he and his teams are always “ready at the pump” whenever any new products are developed.

Recently, the chief accounting officer and his teams have been working to support the launch of a number of new products and initiatives, including a fractional stock trading feature offered through Square’s popular Cash App. That feature will help open the equity markets up to the average American who for example may not have the two thousand dollars required for a full Amazon share but do have say a dollar to purchase a fraction of that share.

“We are constantly rethinking the way that different industries are working in order to increase individuals’ access to the financial system,” Dale says. “And those industries have been ripe for disruption for a while now. We are truly only inhibited by our own pace and velocity and our desire to create something that is remarkable.”

Dale shares some of the key ideas and strategies that have helped propel his own career as well as his teams at Square.

What advice would you give to other finance executives working in disruptive industries?

Trust your team. It’s impossible for somebody to quarterback everything—we move too fast and we have to be too nimble. You have to understand when your team might need your support and when they don’t, but you also have to create a strong values framework so that nobody goes on a witch hunt when somebody does unintentionally make a mistake.

What empowers the teams at Square to feel like they’re allowed to make mistakes?

The tone from the top is critical—a lot of companies get into trouble because there’s a mind-set at the top that everything has to be exactly right, and on time, all the time. Accounting doesn’t always operate with such precision and there are judgment calls to be made.

The culture here at Square centers on learning from our mistakes. When something goes wrong, we hold a cross-functional meeting called a retro: we talk about how to fix the issue going forward, and then we publish the results across the company. We don’t bury our mistakes here—we bring them to life and celebrate them as opportunities to grow. I haven’t seen that sort of discipline and transparency at other companies, and I think it’s what helps people here feel like they are more than just employees. They feel a connection to this place because of the trust that is put in them.

What about your own growth? What makes you feel comfortable taking risks?

Living in the Bay Area for twenty years now, I’ve developed a network of trusted advisors that I can call anytime I have a question. I expect my advisors to have seen a lot more than I have, especially if they’re specialists in a particular area. That network of external voices helps amplify my impact and also helps ensure that the team doesn’t get bogged down in groupthink, which is vital when you’re trying to be disruptive.


CrossCountry Consulting is a business advisory firm that provides customized finance, accounting, human capital management, risk, operations and technology consulting services to leading organizations facing complex change. We partner with our clients to help them navigate pressing business challenges and achieve goals related to improving operations, minimizing risks and enabling future growth. Visit www.crosscountry-consulting.com.


At Grant Thornton Ireland we embrace fresh thinking that moves people and organizations forward, and recognize it takes passion and commitment to achieve growth. We are delighted to congratulate Ajmere Dale of Square on this well-deserved recognition. We are proud to work alongside someone who embraces exceptional leadership and is committed to a re-envisioned future.


At Siegfried, we work alongside executives across the nation on important accounting and finance projects. We provide clients with our unique leadership advisory service, combined with high potential talent. Our Firm’s higher purpose is to help people transform themselves into better leaders to exponentially improve their lives! www.siegfriedgroup.com