Killing it in Silicon Valley: An interview with Sukhinder Singh Cassidy

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Sukhinder Singh Cassidy is one of the most accomplished Canadians in Silicon Valley. She is CEO of small business accounting software company Xero Ltd. and previously led ticket reseller StubHub. She was part of the team that built Google Maps and founded theBoardlist, a talent marketplace that promotes women for board posts. She recently joined the ownership group of the expansion Toronto Tempo WNBA team. She spoke with Sean Silcoff earlier this year. The interview has been abridged and condensed.

Toronto Tempo adds Canadian Silicon Valley CEO as co-owner of WNBA expansion team

You are one of the most successful Canadian tech leaders outside Canada yet you’re not well known in your home country. Does that matter to you?

I don’t wake up and say, ‘Am I well known?’ I don’t really care about my profile in Canada, but I care about Canada, deeply. I’ve been a net beneficiary of this country [the U.S] and part of my identity is here. But there’s this pride in being Canadian that I’ve held onto.

What is it like to be a Canadian in Silicon Valley leading New Zealand’s biggest tech company?

It’s crazy, right? They never asked me to relocate. I think they were looking for somebody who could manage a global portfolio. They knew that Xero was getting to the size where they needed different skills and were seeking a global profile. The good news is it’s just a global SaaS (software-as-a-service) company and not that different than what you’d expect. We talk about the unique heritage of being a Kiwi company – you want to honour the values, you want to honour the pride that comes out of that.

There’s a lot of talk about the [New Zealand rugby team] All Blacks and how you get that All Black energy at Xero. But it’s like running any global company. On the one hand you want to hold it to standards, and on the other you want to honour its heritage. I love the company. They’re just really good people. They share my values. The thing we work on, which we say to investors, is: we have high ambitions to be among the world’s best performing SaaS companies, so we’re upping our performance muscles and our disciplined execution.

You grew up in St. Catharines, Ont., where you’ve said your dad was the only person that wore a turban.

My parents ran a joint medical practice in Tanzania and immigrated to Canada when I was two, mostly for our education. They were in their 40s and had to redo their residency, recertify and start over. Walking through a shopping mall in 1980, people heckled him. They thought he was like the Ayatollah. He was ridiculed, mocked. It was awful. He encountered a lot of racism. But he was loved and respected by his patients, by his community.

What led you to San Francisco?

I was so confused coming out of undergrad [with a business degree from Western University’s Ivey school]. I applied to the foreign service. I got an interview at McMaster’s medical school. They asked me, “Why do you want to be a doctor?” The best answer I had was, “Because I love my parents.” It was terrible. I had a need to prove I could get the top job. I spent two years with Merrill Lynch in New York and London, then moved to broadcaster BSkyB as a financial analyst. One of my American roommates in London went to Stanford Business School. I visited and thought, “This place seems great.” I quit and moved to California in 1998.

Tech is a notoriously male-dominated industry. Did you encounter sexism, and how did you deal with it?

I have not often encountered sexism, but when I did, it was memorable. I started in male dominant industries – investment banking, media – and did well. Merrill Lynch, BSkyB, these were very aggressive meritocratic cultures. I got promoted. I got more responsibility. And then at my first job in the Valley, which was for a startup, the second day on the job my boss said to me, ‘Sukhinder you’re scaring the secretaries.’ I would see this volatile male behavior from one of his buddies that he would placate all the time in public settings. And then he would just give me diminished responsibilities. One day he told me, ‘You know Sukhinder, you’re like the rookie on the field that needs coaching.’ Nobody had ever told me I need coaching. I was miserable. I thought I wasn’t cut out for the Valley.

Luckily, a recruiter called and pitched me on being a product manager at a company called Junglee. I met the three Indian founders who were out of Stanford’s computer science department. They were so smart and straight shooters. My mom was probably happier than she’d ever been because I came to Silicon Valley and finally encountered other Indians. I got the job at Junglee. Day one, I’m a product manager. Day two, they’re like, ‘We know we asked hired you to be a product manager, but we just did this deal with Yahoo and we need to sign a bunch of e-commerce vendors to put their listings on our site. Do you want to just be a business development manager and start calling them?’ There was no telling me I needed coaching.

Your boss, Ram Shriram – an early investor in Google – helped you land a co-founder role at Yodlee, a financial data aggregator, in 1999, after Amazon bought Junglee. How did you end up moving from there to Google in October, 2003?

I wanted to start another company. Ram said, ‘You should go talk to the guys at Google.’ So I went to see the chief business officer, a lovely guy named Omid Kordestani. Omid said, “I have a greenfield opportunity for you at Google. We need to build something in local [search] and maps. Why don’t you come help?” I researched it and realized, “Oh my God, all this local advertising is going to come online.” I joined and did the business development deals to get data to build Google Maps.

You then headed Google’s Asia-Pacific and Latin American operations, before leaving in 2009. You were 39. You must have done well on your stock options. Could you have retired if you wanted to?

Yeah. I just had so much energy. I wanted to build another company. I joined Polyvore [a social shopping platform]. It was a painful six-month stint where I went to be CEO of somebody else’s e-commerce startup. Then the CEO wanted the company back, and the board basically said, “You’re lovely [but] he’s getting the company back.”

All my mentors said, “Sukhinder, get out. You have a board that just signaled to you that they were with you until they weren’t.” I met both venture capitalists [on the board] when it was done and said I’m disappointed by how it was handled. They were apologetic. Startups are a high-contact sport. I swore after that if I would ever be in a startup again, it would only be one that I owned. I tried building a video-shopping network called Joyus, but it was too early for its time. I joined the boards of Ericsson, TripAdvisor and Stitch Fix. I learned that I missed scale.

What had you learned about yourself by this point career-wise?

I learned I’m resilient and agile. I always thought, “I’m not that intense,” but the feedback I kept getting at places like Google was that I’m intense. I’ve learned that I have more intensity than I ever thought, which means that needs to be managed. I learned how to manage people. I learned how to raise money. I learned about my own capacity. I learned about the type of people I like to have around me that made me successful. I learned a lot about values-fit and how important it is to me.

Tell me about your experience at StubHub.

It’s a fun business, but it was slow going. And eBay [its parent company when she joined in 2018] was struggling. I was trying find an entrepreneurial mode. We launched a new set of businesses and were trying to drive our international growth, but nine months into my tenure, Elliott Management and Starboard Value wrote the eBay board, pushing them to divest StubHub. Less than two years after I started, we’d sold the company to a competitor for US$4-billion. The deal closed on Feb. 13, 2020, but they weren’t allowed to integrate because the U.K. Competition Authority thought the combined company would have too dominant a market share. For a year and a half it was under competitive authority and had to be run separately.

By March 13, 99 per cent of live events in the United States were canceled. We had over US$400-million in liabilities and US$100-million in the bank. We had just sold and were owned by another ticketer whose revenues had also gone to zero, so they’re like, “You guys manage it.” Within two weeks we’d furloughed 70 per cent of our staff. We rescinded our policies to offer refunds and instead gave customers a 120 per cent credit for the value of their tickets to be redeemed later. We were hated, lawsuits started. At one point on Twitter somebody said, ‘Sukhinder, I’m coming to your house with a gun.’ I called the police to track the guy down. It was a crazy period. But I’m proud because the company didn’t go bankrupt. I left in June, 2020.

You wrote a book, worked in venture capital then looked for a CEO job. What led you to Xero?

I wanted a bigger total addressable market than StubHub. I wanted tailwinds. I wanted a great business model. I wanted a customer I could be passionate about and a problem I could understand.

Xero was in a rough patch when you joined.

I don’t think you can really say it’s in a rough patch if you have a good business model and a good culture and you’re a bit over your skis on costs. It was very manageable. The company was growing over 20 per cent year-over-year. We right-sized the cost structure, about 900 layoffs in total, sold Waddle [an invoice lending platform], wrote down [workforce planning business] Planday and hired a new executive team.

What’s ahead for Xero?

We’re just getting started. We play in large markets already – accounting, payroll and payments, which account for the majority of what small businesses spend on software. We also play in big country markets. We have the U.S., the U.K., Australia, and seven other countries in which we compete directly, including Canada, and 180 countries in which our software is available. Small- and medium-sized businesses are still digitizing their back office, and governments are still starting to increase their regulation of digitization of tax, of invoicing. There are lots of macro tail winds. Now there’s an opportunity for us to build magical software with generative AI. The opportunity is tremendous for our customers and then increasingly for me as a CEO it is going to change the way people work. At a minimum, the consumerization of generative AI will train the business customers that we serve to expect it in their enterprise software, too.

Why did you start theBoardlist?

Circa 2015, there was a lot of negative press about women in tech. Women were talking about how they couldn’t get funding or asked about whether they were going to get pregnant by venture capitalists. Because I was a founder, I was hearing a lot of these stories. I didn’t experience that, but I’d had Yodlee under my belt and Google, so it was relatively easy for me to raise money. But I’d hear from all these young female founders how brutal it was. On the one hand, I was kind of disgusted. On the other, I was in a cohort of female CEO founders, and they were killing it.

TheBoardlist for me was an attempt to use my voice on gender for the first time, to counteract the narrative that it was terrible for women in tech and at the at the same time say, ‘But it needs to get better.’ Everyone was like, ‘we need more girls in STEM.’ My thesis was, okay, get more girls in STEM, but the Valley is filled with Marissa Mayers and Sheryl Sandbergs and Susan Wojcickis [former leaders at Yahoo, Facebook and YouTube] and powerful women who are knocking the cover off the ball. So why don’t you think about women at the top? One of the things I’m most passionate about is putting women in positions of power. If you really want to change the dynamic and get better outcomes faster, don’t just think about representation at the bottom level of an organization.

DEI has become a dirty word, or acronym, in the U.S. As someone who’s been a champion of the cause and has one of most diverse leadership teams in tech, has that changed how you talk about it?

I’m a believer that diverse thinking drives better performance. The data supports it. And I don’t think that diversity is just gender, ethnicity. It’s also experience. It is whether you come from a Silicon Valley background or not. It’s whether you’ve been in a startup or somewhere bigger. Clearly, I am driving towards building teams that can outperform and thus I believe it’s essential to build diverse teams. I think there’s a false dichotomy in this idea that diversity is the antithesis of performance. I think diversity is highly correlated to outperformance and strong performance for shareholders. It’s simple. Diverse thinking drives higher performance, period. I will always strive to build diverse teams and that has nothing to do with charity. It is seeking to build the very best teams and the very best companies I can.

How do you feel about the fraught state of relations between Canada and U.S.?

For so long we’ve enjoyed a great relationship. I’m a net beneficiary of that. I’ve been able to keep my Canadian identity, my family is all there and yet I’ve built a great career here. I mostly feel sadness. I hope sooner versus later we get out of brinksmanship and back to a positive place. I also believe that America is a capitalistic country and understands economies well and understands that Canada is one of its biggest trading partners. So I believe, at the end of the day, we’ll see resolution.

Have you ever thought about returning to Canada?

What drives me is size of learning opportunities, of impact opportunity. If I were to move back to Canada today, I’d be still looking for the same professional opportunity. I love spending time there. My family is there. Maybe one day I’d spend 50 per cent of my time there, but it’s a different question if you’re asking if I would move back professionally.

The opportunity has to be compelling. That’s how I ended up in a New Zealand company instead of an American one. I was just looking for the best company I could find. The thing I worry about in Canada is you have to make it a friendly environment. There has to be enough venture capital and incentives, like in the U.S. where we have qualified small business stock [which offers capital gains tax benefits]. You have to worry about things like how capital gains are treated. We know there’s great talent there; we bought two Canadian companies. The issue is making sure the environment is conducive from an investment perspective and from a commercial perspective for people to want to build businesses and wealth there. The question is, how do you create policies that encourage or accelerate that growth?

What drew you to invest in Toronto’s WNBA expansion franchise, the Tempo?

I fell in love with basketball over the last 15 years, given the fast pace of the game. At StubHub, I fell more in love with live sports as a fan and as a business category. I learned the businesses of building world-class consumer franchises in sports and saw the appreciation of team values across different leagues – and the continued increase in media rights being negotiated.

After I left StubHub, I identified that I wanted to find the right opportunity to invest in the right franchise, in the right league, where there was the opportunity for long term value appreciation, and where I could align my knowledge and passion for live sports. I honed in on basketball. As a fan, it’s my favorite pro sport. As a business leader, I think the NBA is one of the most forward-footed leagues in terms of building a global fan base and truly global franchises at the team level. I looked at multiple NBA opportunities on the men’s side where there were ownership stakes turning over, but most of those opportunities felt more passive and I felt no emotional connection to the franchise. At the same time, I kept getting approached to invest in professional women’s leagues, including soccer and volleyball. There I felt emotional excitement at investing in the fast growth of women’s pro sports franchises, but was not as excited about the categories where I felt less passion and affinity.

Increasingly, I began to ponder whether the best opportunity to bring together my passion and values was in the WNBA. When I heard Toronto might be bidding on a franchise, I got connected to the ownership group. It finally felt like the Tempo could be the ideal opportunity to have my aspirations come together and be able to participate at the ground level in the investment and building of the team.