Full Transcript

Darren [00:00:03]:

Hi everyone. Welcome back to another episode of One of one. I’m your host, Darren Gold, CEO of the Trium Group. My guest today is Sukhinder Singh Cassidy. In this conversation we cover Sukhinder’s incredible career journey which has included being a two time founder, a senior executive at Google and CEO roles at StubHub and now the accounting software company Zero. Given this background, Sukhinder shares an important and unique perspective on the debate between founder Mode and CEO Mode. She also offers a really helpful view on what it takes to build a truly high performing leadership team. I really enjoyed this episode and I hope and trust you will too. So kinder, welcome to the show. It’s so wonderful to have you here and I’m really grateful for you spending the time.

Sukhinder Singh Cassidy [00:00:55]:

Yeah. Good to see you again.

Darren [00:00:57]:

Yeah, great to see you. I have so many things that I’d love to cover and we’ve got limited time. We’ll try to get to as much of it as we can. I’m sure it’ll be a great conversation. I wanted to start with this great company that you’ve been leading for the now, I guess, past couple years, partly because I’ve been a consumer. My youngest started a small business when he was in high school and we were looking for a great accounting software to help him manage the financial part of the business. And we found Xero and we absolutely have loved the product experience. I mean it is a great product.

Sukhinder Singh Cassidy [00:01:32]:

So, you know, I, I didn’t even know you were a secret customer. Yay.

Darren [00:01:35]:

Yes. Yeah. And I think you were too when you came on.

Sukhinder Singh Cassidy [00:01:39]:

I was, yeah. I mean, so look, Xero, as you pointed out, is small business accounting software that is used globally. Actually, many people probably don’t know Xero because born and bred from the southern hemisphere, it was a New Zealand company that was started 17 years ago, been expanded to Australia, the UK, the US, Canada and South Africa, Singapore, what have you. So I would imagine we’re one of the most global accounting software companies in the world if you think about the markets we play in. And the biggest are the us, the UK and Australia of course, which is our heritage market. It’s cloud native, it connects to all the apps you love so you can use it with every app stack you have. Like in the US that’s particularly important given all the fintech stacks people use. But we also have embedded payroll and payments. So if you want to, you know, manage your cash flow, send an invoice, pay your employees, you can do that on the platform. As you pointed out. We pride ourselves on being easy to use. We’re very friendly for SMBs, but also for those who have accounts and bookkeepers. We have a big community of accounts and bookkeepers that connect with their clients on the platform so they can work together. Companies, multi channel, multi product, multi geo. And most importantly, it’s a group of really lovely people and a wonderful culture. So that’s, that’s zero.

Darren [00:02:50]:

So apart from the product and the lovely people, what was, what was the draw for you a couple years ago or plus when you were considering joining as CEO?

Sukhinder Singh Cassidy [00:03:00]:

Well, you know this because you interview CEOs and you coach CEOs. Finding the right CEO job is, you know, a combination of those things. Obviously you want a great business, a great product, a great culture, but it’s even more right. So when people were asking me what I was looking for in the CEO journey, I said, I know this is a tall list, so just bear with me. I want to be in a category that on the one hand, I have passion for and I love small businesses. They’re very close to consumer. You can get your, wrap your arms around them and think about their journey. Because it’s your journey. It’s my journey. I’ve been a founder. My parents are small business owners. But in. But I also want a category where I’m not just passionate about it, but it’s growing. So I think actually it makes a lot of difference in your career journey to pick a good hand. Right? So you want to be in a growing category. You want to feel like there are macro tailwinds in your favor. And in fact, accounting software is one of the last things to digitize for small businesses. It gives them back time and savings. And we’re still at a very low level of adoption globally and governments are pushing small businesses to digitize more. So I was looking for category of passion and category of growth. And then I’d say lastly, I mean, I’ve lived a lot of different business models, ads, B2B tech kids, you know, Yodeli. One of My first companies, StubHub, was E Commerce and Marketplaces, as you well know, as founder of another e commerce company. But B2B software, you know, strong business model. The customer has a recurring subscription. You know, if you do well by them, they will come back every year. You don’t have to refight to claim them though. You have to fight to keep them and keep doing a great job for them. So I was also looking for a strong business model. So you could, as you can tell, I was really judging the fundamentals of what I was joining because, you know, there are different types of companies you can join and they off offer all offer a different leadership journey. But of course I do believe in being a smart risk taker and maximizing your chances of success by picking.

Darren [00:04:47]:

Well, yeah, I believe you’ve written a book about this very subject.

Sukhinder Singh Cassidy [00:04:52]:

I did choose possibility Step up in zero. I did write a book on taking smart risks. But you know, many people think you just out execute your way out of any problem. And of course I like to think of myself as a good executor, but when people ask me for career advice, I’m like, you know, you also want to maximize your chances of success. Like you want to go to environments where that might be more conducive to that. Right. And so I think that, I think that’s also okay.

Darren [00:05:16]:

So let’s spend a little bit of time talking about your incredible career journey both because I think that will bring to life who you are and bring us to the present day. We’ll come back to zero in a moment. But also I’d be interested in you weaving into your own description of your career journey, some of the choices you’ve made and the meta subject of choices and the path that people take and the mistakes they make, the risk they should be taking and so forth. So take us back to maybe the beginning of your professional journey or whatever, however way you want to.

Sukhinder Singh Cassidy [00:05:47]:

Well, maybe it’s probably best to describe the macro and then the micro. You know, I think people often think that path to CEO seat is linear. It’s not. I mean, you know, you can read articles from the New York Times and on that like everybody takes a path that when you, when would describe it backwards, it sounds so like perfect. But when you’re going through it, it is a lot more nonlinear. Right. And mine certainly fits that bill. And I think that’s. And I think what you’re referencing is I’ve spent roughly half of my career at large companies and roughly half of my career starting companies. And so clearly the arc that I think that fits between those things is growth. I love to build and to grow. And I’m fascinated by almost any problem or opportunity to do that and any opportunity to learn. And so when you move between big and small companies, your own as a founder or as, you know, joining a startup team or a large company like a Google, where I’ve been, or an Amazon or I was at ebay, I guess, When I ran StubHub, part of the ebay leadership team, you have different learning journeys. Right. One is about scale and, you know, optimization and one is about build. And so I guess you could call me somebody who’s very attracted to building and problem solving and I can get passionate about anything, almost anything. So. So that’s the arc. And then I think to your point, I grew up in St. Athens, Ontario. I’m Canadian, proudly. I went to school in Ontario and I sort of, I would say had a. I. We don’t need to go into it, but I had a pretty difficult time for getting my first job. But I ultimately did. Took me about a year and a half and I got to my dream job, which was on Wall street, moved down to New York, was an investment banking analyst and then I moved to London. But as I referenced earlier, my parents were small business owners. And so even though I was in this like, you know, intense, kind of prestigious job for somebody out of school, which took me a long time to get, I really, really loved the idea of being an entrepreneur and I didn’t know how. So I spent a year at a media company, B Sky B, you know, a big media company owned by News in, in London. I was, I was there after investment banking and I basically quit my job and I moved to Silicon Valley and I was like, I don’t know how to be an entrepreneur. I think if I just put myself in quit great weather and this great environment, I’ll figure it out. And so I think that was a big move for me in hindsight because although I didn’t know it, I moved in 1997 and it turns out 1997 is a pretty good time to bet on the Internet. Like, who knew? So I, I mean, this is what I mean about choices. Like I had a thesis about entrepreneurship and I made a small choice that turned out to be a big choice, if that makes sense. Right? Yeah, I quit, I moved. I was 27 years old. I’m like, okay, I’m gonna find a job. I did. I was at a couple of startups, one of which got bought by Amazon and kind of started my career, I guess in earnest at Amazon. And a year later had an opportunity to found a company based on connections, you know, in the Valley. That kind of small mafia of startup founders found me and that company was Yodlee, which still exists today. Yodle is a fintech pioneer. It is sort of the backbone for data for many, many fintech apps you use today, including Xero. We use Yodlee proudly. So I became the business co founder there and spent five years building Yodlee. And its business model and then moved. Interestingly, I thought I’d moved to another small company, but Yodlee’s investors were the same as Google’s And I was lured over to Google and I we talk about thing. Google lured me over. I thought it was so big, it was a thousand people. Google lured me over because as I said, we shared common investors and they sort of came and found me and they basically said, well you know, we have this interesting problem set that we think you’ll like. It’s very startup like and, and Yahoo has like this thing called local and AOL has Maps and Google has nothing. And it took me about two weeks to realize that like the opportunity to build a local or Maps product was pretty darn big. The yellow pages industry was $23 billion. Nobody knows what that is now, but that was the backbone for local advertising. And two weeks later I filled up with a job offer at Google. I left my own startup, I went to Google and my first job was being the business partner to the product team on building local and Maps, so doing all of the deals necessary to get the data to build those products. And a year later Google asked me to move internally to another startup job which was building our international business. And I moved from running kind of a larger team of biz dev folks, you know, to moving to running what was then called Google’s RO business rest of world, which is everything outside of Europe and the US and for the next five years I built our business that became called Appla Asia Pacific, Latin America, from Brazil to China and built that to a couple billion dollars and a few thousand people. So this is what I mean about big and small, right? But I started small. I think you should have like did I know what Google was going to become? I knew it was a good company, but again, think about my journey like in backwards. It sounds so impressive and forward leaning. You’re like, oh, this sounds like an interesting challenge. And that was great. I think from there I was about 39 years old. I actually Googled up very big. I was very senior. But I also really thought if I I want to be a CEO and I think I want to be an entrepreneur again. So I left my big creepy job at Google. I went to a venture capital firm and looked at everything. I had a thesis that E commerce, this is circa 2008, 2009 was going to boom. I joined the board of a retailer called J Crew, which everyone knows. And a year later I joined E commerce startup where ultimately I fell out with the founder we can get into that if we want. But my love of e commerce remained. I’d studied the category and I started a company called Joyous, which, believe it or not, was a video commerce startup. You know, so people are. What do you mean? I mean, I mean, I mean shopping on the Internet through video. I know everybody thinks that’s like a, like, like easy to imagine today. In 2010, there was no TikTok, there was no Instagram video, There were haul videos on YouTube. And every time I pitched the idea, people thought I was pitching them on having infomercials on the Internet. So we built my own patented technology, we built studios, we built a merchandising team. And for six years I ran a business that was like online shopping. Videos grew to about million. Couldn’t get any VC to fund it. Circa 2015, 16. I mean this is like about timing, right? I ultimately sold it and went back to scale. I missed scale. So I ended up joining eBay. EBay offered me the opportunity to run StubHub. We met there, you and I. I became a CEO, I guess, of something larger. Not my own startup, but something larger. We successfully ran that business and sold it right before COVID which is crazy, really, you know, wonderful exit for StubHub. And then ran into Covid, managed that crazy experience, which we’re, I’m happy to talk about or not. Just made sure the company survived after we sold it for $4 billion. I was still on watch when its revenues went to zero. Got that jam, wrote a book and found zero. So that is the arc. As you can tell, it’s like a three time founder and a three time, I guess, larger company executive.

Darren [00:12:37]:

Yeah, it’s an incredible journey. I am curious and maybe we’ll get to what it must have been like to be leading Snubhub at a time, you know, in 2020, your live experiences marketplace. And there are no live experiences. So I’m just taken by the, the depth and breadth and richness of your experiences and also a really grocking the point, which is it’s, it’s not a, it’s not a linear path. It never is. And it does sound nice in hindsight.

Sukhinder Singh Cassidy [00:13:03]:

It sounds. And I’m like all the way through, you know, and like, of course, like good amount of failure in there. People think it’s all successful. I mean, building a video commerce startup, I don’t wake up and ask myself, man, if I went five more years, like, you know, like how the world has changed now, you know, there are rails on which you would and those are big platforms. So maybe my know, maybe my studio would have been the thing of most value. But all interesting. Think about.

Darren [00:13:28]:

Yeah, one of my key thesis and in this work, in this podcast is as I think I’ve shared with you, is that the CEO in particular is an extraordinarily high point of leverage in a, in a system. Of course, it’s more than just the CEO, and I recognize that. But I’m curious whether, number one, you agree with that statement and two, as you were entering the current company zero as CEO, what was your, what was your thesis? What was your hypothesis? How are you planning to use your, the freshness of your leadership and perspective to inflect the business or change the business and how has it turned out?

Sukhinder Singh Cassidy [00:14:02]:

Sure. I’ll take the second question, then we can come back to the question of CEO leverage. So my thesis 1000 first of all is it’s a great business. So, you know, it’s not me. It’s a great business and I’m lucky to enter it. So like, important, you know, important. It’s not all you. It never is. It’s you in combination with your environment and can you bring strengths that are uniquely needed. So maybe I’ll tell you what I and the board both, both thought I saw in common. Number one, you know, great business, still high growth, still needs though like entrepreneurial energy to keep innovating, growing. So they were attracted, I’d say, to that part of my DNA, right. Which on the one hand is product driven. I’ve been a founder. I do think that I have fintech experience. I understood the category, I understand e commerce, right. So like a conflection of things I understand on the product side and how to keep innovating and growing. Number two, a global CEO. And I thought, okay, I do know how to run all these markets. I have actually run the US market, which is one of our smaller markets, but growing. I do know how to run a business. In Australia I ran a whole portfolio of like 180 countries. And so the global thesis, like how do you bring in a global CEO and run this portfolio of global markets and global product? And that’s obviously a very CEO like thing to be able to do, but it also requires kind of a global mindset. And so I’ve, if you’ve given my background, that made sense to me. So I think we, I think they were looking for sort of entrepreneurial energy, product innovation, product thinking, the ability to handle the complexity of a global business and understand how to manage a global portfolio and I thought, yes, I can do this, I can do this. And then three, as I, you know, as we talked about, you know, I think we both saw and you know, pretty quickly at zero, when I got here, the opportunity for it to go from being a good business financially to a great business. And by great business, I mean I saw that it could get profitable. I saw that we were probably a little oversized on the cost base. The board saw, like, man, we have such a good hand. Like, why isn’t this business profitable yet? How do we get it there? And so just optimizing the business model for long term sustainable success. And to your point, coming back to the CEO. Yeah. I mean, people would ask me when I arrived like Sukhinder, is it growth or profits? And I’m like, both. Like a great business model, that means that we can sustainably deliver strong top line growth, be best in class software that is loved by users and yes, be profitable. And so the optimization of that business model, I think that was the triumvirate I saw and I think that’s it. I think that’s also probably why they, you know, gave me a chance at the job. That’s my gut.

Darren [00:16:30]:

Yeah, yeah. I’ve seen you in the role and what I’ve seen is a, I think a really powerful demand for excellence and performance from the organization. I imagine you haven’t changed since we first met and I’m just wondering, you know, how you brought that into this company, how it was met, where you might have been challenged by trying to raise the game a little bit. And you know, where, where have you been successful?

Sukhinder Singh Cassidy [00:16:55]:

Sure. Well, first of all, unfortunately I haven’t changed. Like our strengths are our shadows. So I’m as intense as ever. Um, and so yeah, I did, I did bring that intensity and maybe demanding nature, dare I say zero, but the thing I bought with it and the thing I’ve had to temper, the thing I bought with it, which I think you know, is, is how I’m, I’m like a really open person in some ways. I can’t help myself. Like, I just say it as I see it, I wish I could play a more savvy game. You know, even in this conversation, I’m sure I’m saying a dozen things I shouldn’t, but that is, I have also benefited from being in, I’d say open and authentic with my views. So I think if you’re going to bring that intensity, you have to bring self awareness and you also have to bring openness, you know, and you have to be open to others. And so I do try and meet the world openly and I try to meet Z openly. And I would say in things like cost cutting, I mean we did a major restructure six weeks after I arrived. Yeah, the only way we navigated that was through, I think their openness to me and my openness to them and my plain speaking with them, if that makes sense. Like guys, this is a great business. I’m going to bring you the data from the outside and I’m not going to lie to you. And, and I just felt from day one, my job is to bring optimism but also realism to the job. And so that’s how I’ve navigated it here and I think it’s held me in good stead. Now what have I had to temper? Look, this is a global business. Proudly it should be. You know, it was built from Australia, New Zealand. It’s one of the largest tech success stories. Like it doesn’t need somebody coming in like, you know, imprinting like I come from Silicon Valley, you know, we everything. Like it doesn’t need somebody’s trying to bring like I dare I say it like, you know, like in an American takeover. No, I, like this is a global business and I’m going to honor its roots and its global nature and even the variety of cultures we have, you know, we have, those of us come from Silicon Valley. Yeah. We have this in like intensity and drive and like why not yesterday? And I don’t understand. And I’m even worse because I’ve been a founder which you know, so think about my patience levels is low. And on the other hand we have a culture that is sustainably one of care of treating our people really well. And I want to maintain that. We have, we have different cultural standards around the world. Like we operate everywhere from Singapore to Australia. You know, in Australia they have. And it’s true, there’s, there’s right to disconnect from work legislation. Like that’s a different operating environment. Right?

Darren [00:19:21]:

Yeah.

Sukhinder Singh Cassidy [00:19:21]:

And so zero’s respect, I think, and need me to honor all of the cultures of the business and traverse between them and not just be like, well, my way is the highway. It’s my way or the highway. It’s very much like, okay, this is who I am, this is who you are. And by the way, this is how we’re going to traverse. So things like hybrid work we embrace. I don’t need to be, I mean my own belief set is if it, if I’m asking people to work like four time zones. Yeah. You think I’m also going to ask them, myself included. Okay. Work for four time zones and please come to work at 8 in the morning and go home at 5 and you know, and then get online again. Like, and by the way, spend two hours commuting. Okay. Spend no time with your family. And by the way, I already know you have to get on another call at 9pm because of our time. You have to give people some recognition that we work differently across these places. And, and there’s demand. So I think the thing I’ve had. I wouldn’t even say temper. The thing you have to modulate. You’re running a business with like 5,000 people with five different experiences and how they work and, and, and how they think. The thing I find comfort in, in that, by the way, is our values are very similar. So zero is an open play. And it’s far easier for me to be expected, accepted as a CEO with my intensity by just saying it. Like, you know, people recognize that, so I don’t try and hide it from it. I’m like, guys, this is like, I’m a workaholic.

Darren [00:20:34]:

Yeah, yeah, yeah.

Sukhinder Singh Cassidy [00:20:35]:

Last thing I do. And I think this is important at zero. Was important at. It was important at StubHub, but probably even, even more important at zero. Like, I have a Slack channel. I’m like, you want to ask me anything, ask me anything. You know, I don’t just post about, believe it or not, I post about what I’m doing with my family. Like, I mean, if everybody thinks I wake up every day and I don’t think about that, my own health or the health of my children, like, I’m trying to navigate it all too, just like everybody else. And so maybe I put myself out there even a little bit more at zero because I want people to understand. Like, I, I’m just like you. I’m navigating the same thing. You know, I’m not one person. You know, if you want to define me as being Silicon Valley, you know, type, that would be a mistake. I’m Canadian mother. I love to play tennis. I like, you know, I have 10 identities I’m trying to maintain, and so is everybody. I just like, put out, maybe put out a bit more at zero, given all the different diverse folks we have on the team.

Darren [00:21:25]:

I’m picking up a couple things and I just wanted to, to, to name them and get your reaction to them. One is your ability to handle complexity, and within that, particularly opposites. So how do I have a culture where we’re demanding a lot. So high standards and also high care. And I find the most effective leaders are ones particularly in global complex businesses that are able to handle paradox and, and integrate them. I also have always found in you and I think it’s a really laudable trait. I am who I am and while I’m open, I’m going to be unapologetic about in some ways the way I’m leading this company and what my expectations are with a lot of deep care in that. So I just wanted to synthesize what you just shared. Does that feel accurate to you?

Sukhinder Singh Cassidy [00:22:05]:

I think, I think it’s accurate. I think the more complex an environment, the more you need to help people get clarity and simplicity. And to your point, I do hold paradoxes. I mean it could be true. We’re going to talk, I’m sure in this call about founder versus CEO mode. Like yeah, and people think of that as a paradox. I’m like, no, it’s a paradigm and you have to figure out, you know, how to hold both types of energy if you want to and when to use which. So yes, I do believe that it’s not one or the other. I think that’s accurate.

Darren [00:22:32]:

Well, let’s talk about that because last year if you had to sort of name a theme, particularly in Silicon Valley, and I know we’re speaking to a larger audience and your company is certainly broader in reach, you know, the theme of founder mode was pretty prevalent, I think in some ways misunderstood and misapplied. And in some ways there was a lot of brilliance to the naming of something that a lot of people had been feeling. I know you have a unique perspective. I share it. Like you have such a unique background because you bring founder experience. You also bring professional CEO experience, if that’s even the right way of describing it. And I think you integrate those two things really, really well. But I’d love to hear your perspective just overall because it’s such a, I think, important topic.

Sukhinder Singh Cassidy [00:23:13]:

Yeah, it’s so funny. So long before there founder mode or CEO mode. I’ve always talked, you know, to my own teams and then teams externally. When I speak about operating range and I have this paradigm, it says like there’s this range that says like the founder CEO was like in the details building the product and you know, the founder’s here and the CEO was here. You know, they bring big scale and like a top down view and delegate ability management board. I’m like, and you guys have juxtaposed them here. And I said no, no, what you need to have is as, as somebody wants to lead a company sustainably is what I call a sign. Sign like sign like a sine wave. Right. You have to go up and down between founder energy, between details and vision, between delegating and doing. And so like I’ve always had this idea that you need to have operating right. You go up, down, side to side. And I think to me that’s like very analogous to founder versus CEO. Like no, it’s two types of modalities and at any given time a company needs it, right. So if you want to stay high, I don’t know if you’re driving a product driven tech stuff tech company of any size. I’m pretty sure Sundar Pichar still does product reviews. Right. You know, because he wants to understand like what is it we are shipping, you know, and have a go at the product level. And of course he’ll turn around and then go have to talk to the board about running a multi trillion dollar company. But it’s about putting on the right hat for the circumstance and being able to find that energy. Sometimes when you’re in a turnaround, you want to bring that vision and inspiration, right. Or the grit of a founder or the ownership mindset. Like you all want to live in silos. And as far as I can tell as a CEO, like it is one team and sometimes you want to bring the pound, the table energy and sometimes you want to be able to bring the like it’s going to be okay. Everything has season in a time. We don’t need to do it all today. So of course I, I think you have to find those modalities and many people will argue that they only have one skill or the other. I’m like, you have both within. You might have them in different proportions and then the importance is okay, well if you recognize a team means something else and you can’t bring enough of it, well that’s why you build a team, right? So you can still count on your team to bring more of that energy. Maybe you don’t see yourself as product visionary. Well, have your, you know, chief product officer, you know, speak more, take the mic in, in all hands, like whatever energy you need to bring. So I think you need to sense the time and need for both modalities, find and bring forth the discomfort part of yourself and also use your team.

Darren [00:25:31]:

Yeah, that’s a great point around team and I’d love to just explore it a little bit with you. And we all talk about everybody has a leadership team. We, I think CEOs manage and lead their teams differently. What do you do that might be distinctive or what philosophy or beliefs you hold about the importance of team that might be a little bit unique to you?

Sukhinder Singh Cassidy [00:25:50]:

Yes. Let me think about what’s distinctive to me. I look for. One thing I look for in leaders is people who have high self awareness and who have low entitlement and who have navigated failure and success. I look for diversity of experience. So as an example, when you interview with somebody like me and I say like what’s the hardest thing you’ve ever been to through or what’s a situation in which you didn’t succeed or you know, what do you think your development areas are? And people stumble on those questions and they give me like a non fail fail or a non weakness weakness. I’m like, I’m interested in people with a diversity of experiences who’ve seen a lot and navigated a lot because it gives me a lot of confidence that they have both resilience and creative problem solving. So I think that’s probably unique about me. I know there are people who look for perfect resumes and I know there are people who look for like larger and larger scale or they’ve done the job. Of course in some of these jobs you need the experience. Absolutely. We don’t have time to teach you how to be a CMO as an example, but the converse is I’m looking for people who’ve had a history of impact in a variety of circumstances. Like how have they been impactful, how have they navigated failure? What do they know about themselves that’s going to trip them up and how comfortable and willing are they to talk about it? Then I have a lot more comfort that they know how to build teams that they don’t come into a place like zero which will spit you out if you’re arrogant. And so will I by the way. So those maybe things are things that are distinctive.

Darren [00:27:24]:

Yeah. I’m curious to have a picture of what your leadership team feels like and looks like and sounds like in a meeting where you have a combination of people with high self awareness, low entitlement, a history of navigating and thriving in failure. What does it look like?

Sukhinder Singh Cassidy [00:27:41]:

How would you characterize your team in practice? It looks like a bunch of extroverts and a bunch of introverts and it looks like a bunch of people who are high task oriented and a bunch of people who are very high eq. I will say if you looked at my team, it’s very diverse from introvert, extrovert, so that people who speak up a lot and people who speak up less, which is maybe obvious, but it’s also very diverse in terms of like some people are very high on the task orientation capabilities and others are very high relationally. Like it’s really interesting when you look around the team. So I think in some ways it maybe reflects the things I value, but they’re not, it’s not like every single person has all of it. Does that make sense? That’s okay. You could like, I need people who are more, I would say really high EQ quotient around me because I might care deeply but I might miss a lot of signals because I’m going so fast. Right. So it’s, it’s what you’d expect, Aaron. You never get it all in one person. Right. But you need of course, the raw capacity to do the job. I’d say most teams I build are not political. They are at their nature. I would say if there’s one thing that people who I hire always say to me, it’s like, you know what I really hate political environments. I seem to end up with teams that also like me, a political environment. So I would say I don’t, I count myself lucky. I’ve never had a team that were cat fighters, you know, whatever, half fighting, dog fighting. Internally my teams never really look like that and I count myself blessed for that. But I think there was something about the way we relate to each other that’s pretty open and authentic. But people have a wide variety of styles and they index bike on EQ or IQ or task orientation or relation orientation pretty dramatically actually.

Darren [00:29:19]:

What would you say is the hallmark of a truly high performing team? I’ll offer mine just as a way of giving you grounding. Mine is the ability for people to be really, really direct and skillful in their communication where the percentage of things that are held back is really low. And there’s obviously a lot of things that contribute to the kind of trust and relationship and skill that’s that, that, that enables you to do that. I’m, I’m wondering would that be on your list or what, what’s at the top of your list?

Sukhinder Singh Cassidy [00:29:49]:

You know that’s on my list, but I’m going to offer one that maybe is more tactical, but it is the challenge I have as a CEO. I would say in high performing teams people step outside their box. Okay, so here’s what happens when you’re a CEO. You have really high performing individuals and they have all high trust and care for each other. Okay, so presume that happens. You know where all the messiness in execution is, it’s not within a function. It’s in the distinct projects that cross functions. And you know what every one of your leaders has, they’re pretty, pretty darn busy in their function. So quite frankly there is a unique and I’d say in the highest performing teams you have at least one or two people who will take on the whole and facilitate it. And that is really. And I don’t think you find it a lot. What you find is most teams even appointing the CEO are highly functional teams. Right. And in Silicon Valley even more so because we don’t really arrange by like general management. Like there are some companies in the world where a GM has everything okay. But in most Silicon Valley companies it’s a matrix. So what happens is in the highest, in high performing teams you have high trust and you have directness. That still doesn’t always solve the problem. What I’m needing is one person’s like you know what I know I lead product but I am going to champion or facilitate the whole souk ender. I don’t need you to do that. Like I will drive it through including with my peers. Now that yeah, yeah to me is the highest performing team. If you had multiple people who do that I would say most teams, mine included still fall back to the CEO is the glue.

Darren [00:31:25]:

Yeah, yeah.

Sukhinder Singh Cassidy [00:31:26]:

When they’re in the room with me we can all get on the same page and create a team. But who do I look to say like okay, like if you’re gonna take a, like almost every single project that has complexity crosses functions. And so you know, I think that that is actually the highest performing team. One in which people step out of their functional excellence in telling you their opinion to taking ownership beyond the own self complex things.

Darren [00:31:52]:

It’s a great, a great ad. Totally agree. We talk a lot about, you know, the senior leadership is my first team.

Sukhinder Singh Cassidy [00:31:59]:

Yeah.

Darren [00:31:59]:

The reality is mostly it’s the functional team is my first team and I not nod when yeah well you know.

Sukhinder Singh Cassidy [00:32:05]:

As I always say to you and I say to others, even though I am theoretically a point of leverage and maybe a high point of leverage, I am the only person without my own functional team. So I am the cross functional leader at zero. But I think as you know coming back to the original point, I think the highest performing teams have, I think know that excellence and success is not just about the success of their function, it’s about the success of the whole and they’re willing to risk themselves to Go outside of that. Right. And lead more. Yeah.

Darren [00:32:34]:

It’s almost like having a CEO mindset. You know, how do you. How do you cultivate a CEO mindset in the C level executives, both as a part of their development, because some of them have aspirations, but regardless, to be a great, functional leader and a member of a senior leadership team. You know, building that makes a ton of sense. So I think it’s an awesome point and a great ad. I’m going to steal from it.

Sukhinder Singh Cassidy [00:32:54]:

Oh, good. Yeah, yeah, you should. I mean, and don’t get wrong, Everybody wants to give you an opinion. So it’s not like people don’t come into the room with opinions on how the whole should go. I’m just like, when we leave this room, who outside of me is willing to hold their peers accountable as a me? And that lead means, like, you don’t own it all. You own a good corpus of it, but you have to lead others and lead your peers. And to your point, that is a CEO mindset.

Darren [00:33:18]:

Yeah. There’s a psychological underpinning to that because I think that block oftentimes is, well, it’s my peer. We’re equals, and who am I? And I think what the. What most businesses are calling people forward to do is to transcend that and then skillfully lead and lead your peers and sometimes even lead you. So.

Sukhinder Singh Cassidy [00:33:36]:

Yeah. Yeah. And by the way, I always say, like, every team needs a coach. Right. So I think this is the fallacy. The fallacy is you put a bunch of smart people in the room and brilliance comes out. I’m like, you know this because you are a coach. I mean, the job of the CEO is to get that out of people. Right. In a boardroom without a good chair, that’s. That’s a great experience, you know, no matter how brilliant each person is individually. So to your point, I think this idea that it’s. It’s okay to be a coach of others and to say, hey, I’ll facilitate, I’ll take the lead. You know, I’ll be the person to call everybody else together, you know, to help force a decision to check in on execution. I think that is. I think that is actually quite a rare skill.

Darren [00:34:17]:

Yeah. I want to go back to a comment you made about you have a Slack channel and, you know, you people can post and ask questions. And you’re also very revealing about your. The fullness of who you are, because you’re much more than just the CEO of a zero, even though that’s a huge part of your life. And I’M really curious. You’re running a very complex high growth international business and you have these other identities and other roles and other interests in your life. What is the secret to making that work for you? And I’d love maybe like the day in the life or rituals or some window into that part of how you manage your energy and manage everything you’ve got on your plate.

Sukhinder Singh Cassidy [00:34:58]:

Yeah, I think there’s probably a few constructs I use. First of all, like I’m a, I’m a, like I’m a block of day optimizer. So you know, some people think like you have to always be on or whatever. And I think now, I mean like many people I’m sure like there are just blocks where I need to disconnect and maybe would find that like I think because they think I’m a workaholic. But you know, like by 8, 8 or 9 at night, like I have been going all day and quite frankly if I wanted to in a global company, I could get on five more calls. But I know that if I log in at 9pm and start checking emails, it’s not like I don’t check. But I mean like if I start working again, I can’t even go to sleep. So I’ve learned for myself like, you know what, I am just not looking at my, you know, inbox till tomorrow morning at 7, which would surprise people. But again I try and be a smart time shifter because I know at seven in the morning the, you know, the Australia, New Zealand markets are closed, you know, and so I have like two hours in the morning that nobody else has to catch up on email and do all these things. So as opposed to like respond everywhere, all the time. Now my husband would probably disagree. I think of myself as like a time blocker and the same applies to the weekends. Like people would think like, oh, you know, some people are like, do you have an Apple Apple watch? I’m like, man, if I had an Apple watch I would be checking email every minute. So I actually don’t, you know, like, so I have like, I give myself Saturday. I’m like, you know what, I’m just not good. Look, if I look, I’m getting started. So my rituals, believe it or not, probably more off, off and on than people think. I think people seem always on because I’m you know, generally quite responsive. So that’s one. Number two, I, you know, another thing for me in this off on mode is I would say I flick 50,000 unread emails at any point in time. People Are what I’m like, I pick and choose. I pick and choose in everything. Like, you know, I’m like, the only one responsive to you is if I’m scanning an inbox and be like, of all these things, what requires a response from me? And I just pick them off and I respond. And the rest, I’m like, you know, I’m just gonna ignore all this unread email. And if it’s not to me requiring response directly from me from somebody who is important right now to respond to, I’m not doing it. And so, you know many people. So I just, I’m a picker and chooser. That’s a big one. And I think it’s, it’s. That’s probably a day in the life looks like picking and choosing. So people find me highly responsive because it’s. This is what’s going on in the background. I am quite selfish about blocks of time. You know, like, you know, if I want to go see my son’s basketball game or my daughter’s water polo game, I have no shame whatsoever in saying, you know what, I’m sorry. Like, I’m busy from 3:30 6:30.

Darren [00:37:36]:

Yeah.

Sukhinder Singh Cassidy [00:37:36]:

Because I’m always working. Right. Generally. So. So I, I think that’s sort of how I manage it. And then I pick and choose at home too. Everyone’s like, oh, what’s it like to be a mother? Whatever. I’m like, yeah, guess what? Like, you always feel guilty. Someone’s already always gained the short end of the stick. That’s true. So you know what? I’m not worrying about. I’m sorry. We have a really high doordash bill. It is what it is, you know, I’m sorry. Like, your car is a mess. I’m like, it is what it is. Like, so I. There’s just. I think that’s maybe the big theme. Pick and choose, Pick and choose. Pick and choose.

Darren [00:38:05]:

Yeah. Yeah. The ability to discern what’s important and be comfortable disregarding and letting go things that aren’t or.

Sukhinder Singh Cassidy [00:38:12]:

And then just time blocking, you know, because otherwise it is completely possible to just never switch off. And my mind is already always going, like, if I, if I just kept checking, you know, I literally, I would not be able to sleep because I’d. My, you know, the last thing in my mind is the thing that’s racing. So you really just do have to really be pretty precious about blocks of time.

Darren [00:38:32]:

Yeah. We talked about this in the context of a senior team, like a principle that really guides your philosophy. I’m Wondering if I could ask you the same question about being CEO. If there were one principle that would capture the spirit of the way you think about leading your leadership philosophy that really guides you and animates you and gives insight into you, is there one that comes to mind?

Sukhinder Singh Cassidy [00:38:57]:

I think I have. Maybe I have one. I’m worried it sounds simplistic, actually. My principles impact, I mean, every way. Every day I wake up and I think, can I have the most impact? Every day I judge my team on, are you working on the most impactful thing? Every day I, you know, when I interview people, I say, you know, can you just tell me about the impact you’ve had? Like including impact. When it failed, it didn’t matter, like, what’s the mark you left? Why is something better? Because you spent your time on it, you know, and gave it your attention. So I think the word that guides me, honestly as a CEO is impact. You know, we all have to make choices about where we can be of service and have impact. And I think probably it will probably thread through this conversation. So that’s probably my principle. I mean, sure, there are dozens of other principles I could throw at you, but if you ask me the word it would be an impact.

Darren [00:39:46]:

I’m curious to see, to understand how that shows up. Like, imagine I’m on your team and we’re in a one on one. And like, what would that conversation look like? What was the quality of that principle in action?

Sukhinder Singh Cassidy [00:39:59]:

Quality type, principle in action is I like, here’s a good example, I say to my teams, and remember the other principle I have is operating range, right? Go high, low, go side to side. Okay? So think about those two. Those two. Here’s one example of a interaction. First of all, I asked my teams to always bring an agenda. Of course, always you can do it in a Google Doc. And I’m like, Go 30,000ft, 3,000ft, 300ft. And they’re like, I’m like, just can you categorize the topics we’re going to talk about? I want to make sure that what’s the most important thing to work on? Like what’s at the 30,000 foot? Like what are the things I need to know the right 300ft? Like what there do I need to know about? Because you’re dealing with something at 300ft and hope maybe nothing, right? But I’m like, what are the altitudes you’re dealing at? And so that in our conversation, even in an agenda, I know we’re tracking on all three, that’s impact. That’s sequencing, that’s operating range. So that’s how it might play up. You know, everyone’s like, what’s the most important thing? What’s the most important thing you need to do? But again, I’d rather they bring a very simple framework for that. Right? A CEO. I mean, I have to count on the fact that my teams can sequence and prioritize. But what it looks like with me is I am trying to understand, you know, the things that matter most and how we’re tracking on those, which is so obvious. I would say.

Darren [00:41:07]:

Yeah, but I imagine you’re, you don’t shy away from being directive when there’s a difference of opinion on unfortunately, what’s the highest impact?

Sukhinder Singh Cassidy [00:41:16]:

Unfortunately not. And unfortunately I have a high directive quality. But, but, but to be honest, when you come back to this, remember we talked about self awareness. So if you know you’re a highly directive person, that’s another reason my teams need agendas. I always say, come in with your agenda and your thoughts. What chance you’re leaving with your agenda and your thoughts. Come in with no agenda. You’re leading with my agenda. I’m not saying you’re wrong. I’m just saying you’re interacting with somebody who always has an opinion and whose mind is always like, oh, what’s the most impactful thing? Right? So what, as an example, when my mind’s worrying that way, I will shoot my teams and know and be like, hey, on our next one on one, can you add these things to your list so I know the things I’m thinking about are covered, right? Because I’m obviously thinking about a dozen things anytime. But I think the way to be in command, which is really important with the CEO is very simply, it works with me too really well. I’m like, manage up. It’s really simple. Bring your thoughts, bring your point of view, bring your structure. All I need is structure and a great interaction. And I’m good because I have a dozen other problems to solve. So I think people, when they encounter somebody who can be more directive, will be like, wow, if you’re just going to tell me what to do, I’m like, no, you’re a leader. Like, you come in and you tell me what to do. Like, I actually enjoy those interactions, believe it or not. I’m like, oh, that was really simple for me. I just had to say, yes, no, maybe. And nine times out of 10, I’m going to agree with you. You’re the, you’re the expert, right? So even it helps with that directive Tendency, if that makes sense.

Darren [00:42:37]:

Yeah, I want to maybe round out our conversation and close out, start to close out our conversation but really to have you think about the next couple years at zero and your own leadership and your own role and if you had to sort of describe the continued evolution of Sikhinder over the next, let’s call it two years, what would that, what would that look like? What, what are your hopes and aspirations for yourself?

Sukhinder Singh Cassidy [00:43:00]:

Right. Well first of all I’m somebody who thinks like the continued evolution of security has to be in service of zero. So I think of who I am and what I do and what I’m meant to do and my purpose all intertwined in the same thing. So like if I have an agenda that’s different from zeros for my growth, I would be pretty upset with myself. So that’s, that’s just the way I roll Xero. Let’s start with Xero. Like look, zero is my agenda is very simple. We have the opportunity to be a world class company in our category when it comes to delivering amazing software that’s increasingly magical for our customers. And you can imagine what that means. AI, all these other things but like a delight product and an excellently run, you know, financial machine. Yeah, High growth, high profits, high care, high performance, like that’s it. So that’s the journey Zero’s on and it’s a continual journey and it doesn’t end and that’s great. All that happens every year is the bar gets set higher as it should. Like that’s great. Like good for us that like, you know, we are growing as a team and as a company and as far as we can see we have a lot of Runway, we have a lot of things to do. You know, it’s like it is a growing category and our customers need more time back from us every year that. So what does Xero need for me and where do I need to grow? Well, you can imagine first of all like everyone I need to keep up leveling my team’s capacity and capability to take on more so that I can go, I always think like of drafting right. So I can go draft around the next corner and start thinking about the things Xero is going to need a year from now. So probably needs, I need to keep modulating my style like making sure we have the right talent not just at one level of the strategy but the second level, third level. I’m a believer that you know, unlocks happen like maybe at a director or product lead level for a key area. It’s not going to happen because you hired the person at your levels, because they hired the right person and their team is firing. So I care probably about the development of our top 100 leaders, right? And for me that means like what services, what programs they need, how do I need to show up as a leader to get the best from them? I think a lot about that. How do I need to. My style, that’s part of Sukender’s development problem is also like as the business go gets more complex, everything gets more complex. Like how we deal with our board, you know, how we take people on a bigger strategy journey, how do we think about our investor base? So I think what, as you get bigger and in some ways more relevant, all that happens is demands on you increase. And so I think I have a coach, you know, I have, I have a set of things that people need from me all the time and I again, I’m just quite simplistic. Like I’ve got to keep improving my game, but that depends on the team I build, grow and foster. It depends on my own self awareness and depends on me tapping into some of those other modalities. So I mostly think that I’m capable of growing if I stay self aware and keep looking around the next corner. Does that make sense? It’s all kind of a virtuous cycle. You know, when you need scale, I’m like, of course I need to keep scaling myself and keep developing new modalities and all those things, but I have to look at this toolkit I have and you know, it’s a system and the system’s gonna run at another gear and another gear in another gear. And so for me, for me to find my next gears, I’m gonna run the same playbook. I just have to run it, you know, at a next level of performance. And so yeah, I, I guess I’m not somebody who worries too much about whether I can do it. I think I need to stay self aware and keep building great teams and keep trying to look around corners and be precious on my time and priorities and keep obviously, I hope, evolving as a human being. But you know, hopefully all in all, good ways.

Darren [00:46:31]:

Yeah, well, I’m also struck by the sense that you’re having fun in this role.

Sukhinder Singh Cassidy [00:46:35]:

Yeah, yeah, I said, I said I like growing and I like creative problem solving. And so it’s really fun to be in a job where every year the challenges are different and they look different and you get to do it with the team you love. Right. I do love working with people. I’m Half introverted, half extroverted. I’m very, you know, I’m very independent, but I get energy from people. I get energy from people solving problems, and I get energy from having impact. So for me, as long as things are true and I’m with the tribe I love and my family’s healthy and my children are dead, then, like, what do I have to complain about, right? I. I get. I get something amazing.

Darren [00:47:11]:

Yeah, We’ve. We’ve covered so much ground. It’s been awesome. I wanted to give you an opportunity. If there’s anything that we haven’t covered that you’d want to add or something that we have that you want to say differently or synthesize. There is anything.

Sukhinder Singh Cassidy [00:47:24]:

Oh, gosh, I don’t think so. I think we’ve talked about a lot, and I. I mean, I think you covered the essence of. Of most. And, you know, thanks for being a great interviewer.

Darren [00:47:32]:

Well, thanks for making it so easy. It’s been delightful. I was so looking forward to it. And again, I really, really appreciate you and. And the time.

Sukhinder Singh Cassidy [00:47:39]:

Thank you.

Darren [00:47:48]:

I hope you were able to get a full appreciation of Sukhinder’s incredible leadership style. A unique combination of authenticity, care, and an intense drive for impact. I look forward to being with you on the next episode of one of One. Until then, I hope you live and lead with courage, wisdom, and above all, with love.

One of One is produced by Erica Gerard and Podkit Productions. Music by John LaSala.