🤝 Meet Sukhinder Singh Cassidy. She’s the CEO of global software provider Xero, a minority owner of the WNBA’s Toronto Tempo, and a Silicon Valley veteran. We sat down with Sukhinder to talk about the SaaSpocalypse fears, how she built the first iteration of Google Maps, and what she learned from her colleague’s free fall from the edge of space.
What does Xero do?
We are a global-based software provider to small businesses. We help them do accounting, payments, and payroll. We have about five million businesses worldwide, including in Canada, of course, but also Australia, the U.K., the U.S., South Africa, New Zealand, Singapore — 180 markets in all. We also serve hundreds of thousands of accountants and bookkeepers who are often their financial advisors. We did NZ$275 million in revenue this past year, growing 31%. We generated about $800 million in free cash flow.
You were part of the team that built Google Maps. Did you know back then the product would become what it is today?
Google Maps was the opportunity that got me to leave my own startup. I was a co-founder running business development at Yodlee, and Google and I had met maybe eight months earlier and I'd said, I don't know if I want to come to Google — it's big, it's about 1,000 people, I don't know if I want to not be an entrepreneur again.
Then they called me up and said, we have the Google Maps opportunity for you. I researched the opportunity and thought, oh my god, big industry, big opportunity. I moved over, quit my job at my own startup, and moved to Google as a sole contributor. I partnered with a guy named Bret Taylor, who now runs Sierra and used to run Salesforce. I did all the business deals to get map data, local data, all the data in, and we built Google Maps. It’s crazy to look back on. It was just myself, 10 engineers, and a product manager.
What was the biggest challenge of doing that from scratch?
First of all, you had to work with all the yellow pages companies and mapping companies to license their data, and they were obviously all nervous about Google entering the space. Ultimately you had to convince them there's an opportunity to create a disruptive new product that would grow the pie, even though it would change the pie.
So I'd say the challenge was those deals. They were very proprietary with their data, but that data was essential to get into the product. The core of a maps product is mapping data, and then of course search data on local businesses — their addresses, their phone numbers, all of that. So I'd say it was unlocking those companies. And then, of course, over time Google built its own mapping capabilities to augment what they got from third-party providers.
You were the CEO of StubHub when the pandemic hit. What was that experience like?
Sometimes you can't make this stuff up. I think this is what happens when you've been in tech for a while and see a bunch of cycles. An activist investor forced the sale of the company, so after about two years as CEO I had to lead a sale process. We sold the company for $4 billion on February 13, 2020. We were still waiting for all regulatory approvals of the deal, but the deal had gone through. Around March 8, the pandemic started hitting companies, and I said to my team, "how bad could this get?" And they said, well, maybe by the end of the week 30% of events will be canceled. By the end of the week it was more than 95%.
If you do $5 billion in ticket volume a year, that means you're doing more than a billion dollars a quarter, and it means at any point in time you have a certain amount of liability, because you've taken money from a buyer but you don't hold it — you give it to the seller because you think the event's going to happen.
Because we had been bought by another private company that was also a ticketer, at the time we sold, we had $100 million on our balance sheet and we had liabilities in excess of $400 million to customers. So we ended up furloughing two-thirds of employees. We issued new ticket policies — everybody who was mad about this as a consumer will remember it. We put out policies that said we can't give you cash refunds right now, we can only give you a credit that's more than the face value of what you paid us — we issued up to 120%. Ultimately we managed through the pandemic. So yeah, crazy time. I remember thinking, it's a good thing I know how to be a founder and manage cash — because how did I ever know I might have to run this big platform on cash?
Where does that rank in terms of the challenges you've faced in your career?
I think it ranks higher in terms of the craziest stories, but probably among the top five challenges. Most of the challenges you face are known, they're drawn out over your career. But you will also have what people call black swan events. COVID was a black swan event. The financial crisis in 2009 was another — maybe some people would say it could have been predicted, but for those of us in tech, we didn't know there was going to be a mortgage crisis. There are just times these things happen that you don't think you'll ever encounter, and then you do.
What do you make of SaaSpocalypse fears? Do software companies still have a real moat in the AI era?
We think we have a moat — more than a moat, we think of AI as a tailwind. What do I think is happening in the market at large? I think the market hasn't discerned, in totality, the difference between software companies that will benefit from AI and those which AI will potentially threaten the existence of. It's just lumping them all together.
We see ourselves in the former category. Our customers are small businesses who are short on time and often short on cash. Most of them do not have big technology departments. Who do they look to, to give them technology at a good price? People like Xero. They need us to bundle in features like AI and teach them how to use it. So I think you have to be able to discern between those who have deep, enduring, multiple facets of value, and those who are a thin application layer of software only. We would consider ourselves very durable infrastructure, data, application software, go-to-market innovators, for whom AI is a tailwind.
Do you think the market will eventually be able to differentiate between those types of software companies?
Eventually. I think what you saw in the SaaSpocalypse — if you think about the tail end of '25 into '26 — I think it's just a broad market sell-off. We just focus on creating value. This last year we grew revenue 31%. We got 5 million customers just this July. We believe for our customers, AI can be a multiplier of the value we give them.
You've talked about the importance of maximizing the fear of missing out. What was the genesis of that mindset?
I’ve learned that you have to minimize your fear of failure and maximize your FOMO. If your fear of failure, what I call FOF, is even bigger than your FOMO, you won't act. So where most people say visualize the positive, I would say visualize the negative, pre-mortem the failure state, think about what you would do if that happened, and try to shrink it enough to act. It's very similar to Jeff Bezos's thesis when I was at Amazon — he used to say most decisions you'll make as managers are two-way doors. If you go through and something goes wrong, you can come back.
When I was at Google, I worked with a guy named Alan Eustace, who was one of the original VPs of engineering. Alan ultimately took a sabbatical because he wanted to build a human flying machine. He morphed that into an ambition to create a suit that could take him to the edge of the stratosphere and parachute down. Not only did he make it to the edge of the stratosphere and skydive down, he set the world record for speed in doing so, and survived. And this is not a daredevil, this is a very deliberate engineer. I asked him, “Alan, how did you do it?” And he said, “well, we practiced every failure state. We pre-mortemed every scenario.” So by the time he went to the edge of the stratosphere and jumped out and free-fell for minutes, his heart rate stayed completely steady.
You’re a big tennis fan. Who are your favourite players to watch right now?
There are so many. I'd say, first of all, the GOAT — Novak. That guy has so much grit. You've got to give him credit, he's going after 25 Grand Slams and I think he'll make it, but he's such a competitor, it's crazy. So Novak's probably one of my favourites. Of the young guys there's so many right now, but, of course, Felix Auger-Aliassime, our fellow Canadian. Every morning I get up early — I have the Tennis Channel — so I watch some matches before my day starts.
You recently became a minority owner in the Toronto Tempo. What's been the coolest part about owning a professional sports team?
My love of sports has been long, but obviously it was cemented by running StubHub, because it's an entirely sports and live events experience. I think the coolest part has been being a part of the ownership group. It's the most diverse ownership group I've seen in sports. You've got myself, you've got the Williams sisters, Lilly Singh — one of YouTube's biggest stars — you've got Masai Ujiri, the Lowrys who just joined, the owners of the Montreal Canadiens, the owners of the Ottawa Senators, and Larry Tanenbaum. When I sat in the ownership meeting, sitting around the table watching all of the diversity of experience, gender, ethnicity, just the representation in the room — that is my favourite part of the Tempo.
Any other future sports ventures on the horizon?
Well, I have one other sports interest that I'm not allowed to talk about — I do have an ownership position in another team, but it's confidential. Sports as a category for investing is a scarce asset. It’s a new institutional class that’s historically pretty homogeneously held. Women's sports is an incredible financial opportunity, but I also care a lot about equal footing on who gets to own teams, not just who gets to watch.
This interview has been lightly edited for length and clarity.
