The Leadership Lesson Xero's CEO Learned from a Tennis Legend

Dow Jones
Aug 12

When I spoke to Sukhinder Singh Cassidy, CEO of Xero, in early June, she said she didn't want to talk too much about the company's share price. Our conversation veered back to that topic a few times anyway.

At the time, the New Zealand-founded and Australia-listed maker of accounting software for small businesses wasn't a market darling. Its share price was down more than 50% from one year prior even though the company beat revenue estimates for its fiscal 2026, which ended March 31. The drop was partly attributed to the "SaaS Apocalypse," but also to investor concerns about the impact of a 2025 acquisition, a move the company made to expand the business in the U.S.

"The company is doing extraordinarily well," Singh Cassidy, a former Google and StubHub executive who remains based in Silicon Valley, told me. About AI and the company's AI strategy, she said, "we're going to be a net beneficiary."

"The market's reaction to SaaS companies being completely undifferentiated...that's a moment of challenge," she said.

Spoiler alert: Xero's share price began to rebound in late July, following a leadership change for the U.S. business and positive chatter about the company's valuation, among other shifts. It's up nearly 12% over the month.

Leaders have to develop a mental framework that can help them weather frustrating periods, and Singh Cassidy said she has found tennis useful in that regard. (She rediscovered the sport during the pandemic.)

"It's a game where you can, theoretically...win less than the majority of the points, and still end up winning the match," she told me. "When I am down three games in the first set, what I think to myself is, 'This match is going to go 30 games."

As someone who lives constantly in the future "like many CEOs," she also said the sport is "probably one of the best things for my mind to just live in this moment once the shot is on."

Then there was the mindset trick she learned from 88-year-old tennis giant Dick Gould, who was the men's tennis coach at Stanford University for nearly four decades.

The CEO once took a lesson with Gould along with other tech leaders, she said. Gould was "older and joyful," she recalled, "and I remember this point he said to us. He's like, 'Look, guys, every time I step onto the court, I just tell myself on every shot: Relish the challenge. Relish the challenge. Understand how unique a position you're in, and relish the challenge.'" It's a simple idea, she said, but true.

Xero and Singh Cassidy still have much to prove to investors, and the CEO has more recently faced some scrutiny in Australia over share sales and high-profile departures. But she told me that Gould's three words come to her when she's behind in a game, or explaining the disconnect between the company's results and the market's perception to employees. She encourages employees to forget about the share price and focus on the work.

"It's very much a mindset of, Hey, challenge is a privilege,'" she said. "Honestly, being able to play the game is amazing.'"

Lila MacLellan

Editor, CEO Brief

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