Sukhinder Singh Cassidy on Counting Failure as Success

Sukhinder Singh Cassidy, CEO of tech company Xero, counts her failures as successes, saying it makes her a much better leader.

Current role: CEO, Xero
Tenure: Almost two years
Previous roles: Founder, theBoardlist; president, StubHub; founder and chairman, Joyus; CEO, Polyvore; president, Asia Pacific and Latin America operations, Google

How do you describe great leadership?

Great leadership is impactful. It leaves any place better than you found it and creates positive impact for your employees, your customers and for the world in which you operate.

Xero is the second-biggest tech company on the ASX. What’s your overriding ambition for the organisation?

For us to meet our mission and purpose, which is to be the most insightful platform for small businesses and their advisors globally. And it’s to make lives better for those small business owners and communities in which they operate. Like any good company’s mission, ours is infinitely ambitious. We’re never going to reach it but it’s about unlocking the scale of impact for small businesses. We have chapters of ambition and a never-ending goal.

Isn’t that every CEO’s mantra? You get here but then you have to get there? 

Of course it is. I never rest. There are hundreds of millions of small businesses around the world and in every economy in which they operate, they are a vital and driving force economically to job creation and GDP growth. So by serving our customers, we serve economies around the world. I don’t think you can meet that level of impact if you define it by a single country. That’s why we pursue markets like the United States, because we know it’s an extraordinarily large SMB market.

The tech industry doesn’t have a great reputation for fostering female talent. Is that changing and how will you improve it?

Are there more female founders than when I started? Sure. Are there more female creators of unicorn companies? Yes. On a relative basis, has it gotten better enough, fast enough? I think we would still say no. A very small proportion of dollars goes into funding female-led founders; a very small proportion of capital is controlled by female-led investors. The numbers are still not where they need to be. So what are we doing about it at Xero? We’ve been pretty forthcoming with setting gender and underrepresented people targets. I think we are – and I say this very proudly – the antithesis to the US backlash against DEI [diversity, equity and inclusion] right now. We’re proudly inclusive and focused on equity of all kinds in representation. We’ve reflected that in our targets and our disclosures, in our annual report. Our board is 40 per cent female. Sixty per cent of our leadership team is female. I’m proud that we have a leadership team that looks like the world looks but the sad truth is that it shouldn’t be notable.

Can I take you back to your second day in Silicon Valley in the ’90s? A male boss pulled you aside and told you that you were scaring the secretaries. What was that all about?

I don’t even know. At that point, all I’d done was go to the bathroom, go to my desk, get out a pen and a piece of paper. When you say that to a 26-year-old woman who has four years of work experience, you have to think about what you’re saying. I had been used to being in very aggressive and, quite frankly, far more male-dominated environments like finance. And I had been given a tonne of responsibility; people just let me run. So for me to go to a more meritocratic place and have that commentary passed on me before I had even done an ounce of work was unfair. I was confused and in the ensuing weeks and months, I got fairly menial work. And then I saw some very volatile male behaviour being rewarded at work. I was never going to thrive there; I didn’t feel valued and I questioned everything about myself and whether I belonged in Silicon Valley. In hindsight, I believe that was an unfair experience and you can tell I still feel that way because I can talk about it with some passion 30 years later.

It takes bravery for a young woman to speak up, doesn’t it?

I didn’t even really speak up. I said a little bit but mostly I just cried. I cried at work. I cried in the bathroom. I cried at home. It’s not like I was sexually harassed. It was much more subtle than that. Unconscious bias shows up in a lot of ways and I think when there’s a power dynamic – and even when there’s not a power dynamic – it’s really hard to speak up.

You’ve said that your path to CEO has been a winding one. Has that been a real advantage for you?

I think so. When I was writing my book [Choose Possibility, 2021], we did a tonne of research that shows people take a far more nonlinear path to success. It’s often defined by flexibility, agility, a learning mindset, right? These are maybe the commonalities you find in that winding journey, taking on the hard assignments. So yes, I think that’s been an advantage because it’s taught me flexibility and resilience, which are very endearing qualities for long-term success.

You’ve also described yourself as having the heart of a founder and the training of a professional executive. That sounds like a pretty good mix.

I’m not sure it is such a good mix! Well-trained executives don’t get as impatient or irritable. They’re not as stubborn; they don’t want opinions on everything. I wouldn’t say it’s an easy combination because sometimes you take things too personally. The good news is that when you have been a founder, you wake up every day and have gratitude that you have four million customers. You can’t take that for granted and so few people ever get there. I’ve been on the other side, you know, counting customer one, 10, 100, 1000.

Before you joined Xero, you wrote your book and sat on a couple of boards. How valuable was it to take that time and really think about your next move?

I have always taken time between jobs to think about moves, mostly because when I’m in it, I’m in it. But when I’ve decided that maybe I’ve done all I can do or had all the impact I can have, I’m intentional about what’s next. And I often feel like it’s very hard to know that without stepping back and taking a breather. I feel like these are very important moves and I want perspective.

And how did you assess Xero to ascertain it was the right fit?

Oh, it was easier than you’d expect because I had a long checklist and very few companies made it. When Xero showed up, I said to my husband, “This is the one.” I was already a Xero customer. Then the checklist was simple but hard to fill. I would say to recruiters that the CEO job needs to be open. It needs to have macro tailwinds – the world needs to be moving in the same direction as the company. I like swimming in favourable waters. It needs to have a very robust business model and it needs to be a product I can get passionate about. And it needs to be in line with my values. In two years I saw two opportunities that fit that bill, one of which was Xero.

You’ve talked very openly about being sacked from a startup. I know it was painful at the time but you’re grateful for that experience now, aren’t you?

It taught me grit, resilience and the things I value. I never want to be in a boat with somebody who doesn’t share my values. I made the decision to be CEO, to go to e-commerce and to join Polyvore. I’m really happy with two of those three decisions and they led me all the way to Xero.

Does having more failure than the average person make you a better CEO?

For sure. Because life is a portfolio of bets. I am somebody who believes that if you make more choices, you’ll see more success and also more failure. Making one choice and counting on that single choice to be the path to success feels foolish to me. Everything you try is not going to work. Some things are highly assured; other things are highly speculative. I’m quite comfortable taking risks because I don’t know how you create change without risk or how you innovate without risk. And I also don’t know how you outrun the market without a portfolio of risk. What are the sure bets, what are the adjacent bets and what are the moonshot bets? That portfolio can produce really extraordinary returns if you have the right allocation in each bucket.

So how do you help people take risks?

You have to create conditions that give people frameworks. At Xero, we have a risk radar. We rate the risks – what could go wrong? Let’s identify the prospectus and the risks. For example, nobody knows how to predict what a new product is going to do in terms of behaviour. So when people give a forecast, can they give me a high, medium and low forecast? It’s okay to have volatility in results. That helps people understand how they can actively take risks and be rewarded for telling you about the volatility, identifying the risks upfront, the mitigants and telling you what their escape hatch is. I think you have to ask those questions and then you let them run.

You’re launching an AI chatbot called Jax. What are you learning from it?

The use of a conversational agent to do things that typically would require you to hunt for information offers very quick rewards. But at the end of the day, Jax’s job is not only to be a conversational assistant but to automate tasks in an otherwise onerous world called bookkeeping and accounting. The first task we’re launching with is the raising of an invoice. Why do you have to type out an invoice? Why can’t Jax just create an invoice for you from email or a text message? We’re starting with simple tasks, which is different from information retrieval, and that’s what we’re excited about.

Are you more excited about AI than fearful?

I’m more excited. In the case of Xero, we’re very responsible with the use of our data. It’s in a hosted environment, we have a proprietary dataset, we think about how we train the OLMs [organisational language models] and how we create boundaries for them to prevent hallucinations. In the world at large, I understand why people are fearful. But I’m excited because I feel like we’re putting guardrails on the tech.

Are you the type of leader who likes to feel uncomfortable in a role so you’re always trying to stretch yourself?

Historically, yes. If I don’t have something new challenging me, I’m likely to go and find it. I’m not very good with the status quo; I feel like my brain needs to be fed. I have a lot of intensity and I’m fairly sure I’m ADHD, though I was never diagnosed. I get joy from intellectual stimulation and challenge.

What advice would you give a brand-new CEO?

The work doesn’t happen at your executive team. Two, three, four levels away from you are the superstars who are driving your business. Get close to them. Understand what they’re doing and connect with them. Don’t let hierarchy reign because you won’t know what’s going on. Gather that whole community together and learn, listen and connect.

Take-homes

Personal motto

You don’t know if you don’t try.

Email approach

On average, my inbox has about 50,000 unread emails so I’m not responding to every email. If I spent all day long clearing out my inbox, I’d get nothing done.

Motivation tactic

Recognition. Nothing is more motivating for the team than to stop and be like, “Hey, you know that thing we said we’re going to do? We just did it. Thank you.”

Productivity hack

I don’t respond to things that don’t require my direct involvement. The biggest protection of my time is that I only enter certain morasses and I cherrypick.

Business book

My most recent favourite is Strategy Beyond the Hockey Stick [by Chris Bradley, Martin Hirt and Sven Smit]. I make everybody read it.

A rule you don’t break

Say what you mean.

Favourite piece of advice

My father always said, “It’s not all about you.” He never talked of the “I”; he always talked about service. I live in this larger world with a lot of perspective and gratitude.

SEE ALSO: Adam Goodes Refuses to Compromise on His Values