Booted from a tech startup, this CEO is now leading a $20 billion ASX giant


Sukhinder Singh Cassidy opens up on the philosophies that have taken her to the top of the tech tree and leading a $20-billion ASX-listed company.

Xero CEO Sukhinder Singh Cassidy has had more failures than most,. And she’s okay with that.

The leader of the ASX’s second largest tech company, Singh Cassidy was ousted as CEO of tech startup Polyvore in 2010, after just six months in the job. There were uncontrollable tears, she told the Forbes Australia Women’s Summit.

Singh Cassidy had left a big job at Google as President, Asia Pacific and Latin America Operations, to join the 10-person start-up. “I thought no one will ever want to hire me again… Never again will I go to somebody small and be at the risk of somebody else.”

But she went back to her philosphy of taking small risks.

“I think I’ve had more failure than the average person.” But the daughter of Sikh migrants to Canada from Tanzania said it was important to keep such things in perspective. “I was raised by two parents who were doctors … I was healthy, my parents were healthy. That’s a great position to take risks from.”  

When she was at Google, Singh Cassidy said she wanted to generate a “pipeline of possibilities” for herself in much the same way that CEO Eric Schmidt wanted to do it for Google. “I wanted to be a CEO, I thought I wanted to be an entrepreneur, and I wanted to be in e-commerce.”

She took her time talking to a lot of companies. “I came upon Polyvore which was a really early version of Pinterest and fashion search which had a lot of great engineers. I said to my husband, ‘this is the one’.” Six months later she’d been ousted by the board. “The founder and I saw the world differently.” There were tears. “I gave up this great job at Google for a 10-person company.”

Singh Cassidy’s mentors convinced her not to fight it. “Why would you ever put yourself in the situation where you’re working with people you don’t trust?

“At the end of the day, all this stuff will happen, the world will go on … That’s the underlying thesis I have.”

She went out and founded Joyus – a convergence of content and e-commerce – which sold for a reported US$50 million to StackCommerce in 2017. She became president of StubHub, a US$5 billion turnover ticket resale business. “I led the sale of that business. We sold it right before COVID for US$4 billion,” she told the summit to wild cheers.

“The point of this story is that I set out with the goal to be a CEO, to work in e-commerce, to be an entrepreneur. I was an entrepreneur, it didn’t work but it was scary and innovative and because I was an entrepreneur in e-commerce, I got the call from StubHub.

“I tried one it didn’t work out, I tried three and they did. Sometimes it’s about the learning.”    

Singh Cassidy said that her success has been built on two foundations. Her doctor father taught her the importance of understanding the accounts in a business. “The second thing I learned was to sell. Financial literacy and learning how to bring in the dollars have taken me where I am now.”

But she said her principal business philosophy was about creating a “pipeline of bets”.

“Think about taking risks as a portfolio of choices. People say ‘I’m going to quit my job because I’m really unhappy.’ I’m like, ‘that’s one decision. Open up to possibility. Have you got a second decision, or a third? Before you take the leap, why don’t you do a risk calculation … Nobody’s telling you to make all these decisions today. Have a pipeline of possibility. Generate a list of nine or ten choices and optimise between those choices.

“If you can generate possibility yourself and you have choices every day, you have power … Just keep choosing, whether you fail or succeed, keep choosing.”

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