From XU Magazine, 
Issue 36

Q&A with Sukhinder Singh Cassidy, CEO of Xero

This article originated from the Xero blog. The XU Hub is an independent news and media platform - for Xero users, by Xero users. Any content, imagery and associated links below are directly from Xero and not produced by the XU Hub.
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In the field of financial technology, Xero has long been recognised as a trailblazer, revolutionising the way businesses manage their finances through its innovative cloud-based accounting software. With the recent appointment of a new CEO Sukhinder Singh Cassidy, Xero is set to embark on an exciting chapter of growth. In this exclusive magazine interview, we have the privilege of delving into the mind of Sukhinder Singh Cassidy, a visionary leader who brings a fresh perspective and a wealth of expertise to this influential role.

XU: As the new CEO of Xero, what attracted you to this role and what do you hope to achieve during your tenure?


What attracted me to Xero was the opportunity to make a difference in the lives of those running small businesses and their advisors around the world. Growing up I helped my mother and father run their own business - a medical practice in St Catharines, Ontario, Canada. When I wasn’t at school, I was helping them complete their general ledger and file taxes, all by hand and from the dining room table. During the summers, I was working the reception and looking after our customers, so I really began to understand how important small businesses are to the communities they serve.

So as you can see, helping small businesses succeed is a deeply personal motivation and passion for me, and why I’m so excited to help drive the next stage of Xero together with our customers and partners.

XU: What are your plans for the company’s future growth and innovation? What are the key areas you believe will drive Xero’s success in the coming years?


Xero has been operating for more than 17 years and we now have more than 3.7 million subscribers globally. Our long term opportunity is still really significant. The total addressable market for small businesses in the regions we operate in is estimated at 45 million - and that’s just the English speaking markets. We’ve still got so much space to help drive cloud accounting adoption, which we know has huge benefits for small businesses of all kinds especially in navigating challenging or changing economic environments.

We’re really positive about the multiple levers Xero has to deliver growth - including driving further adoption of cloud accounting with new customers and deepening customer engagement with our existing customers.

One of my top priorities is to be more customer-centric - to be responsive to and guided by our small business customers’ evolving needs. That’s a really exciting challenge for us as a global company and a huge opportunity to get closer to small business communities around the world.

Longer term, there are three important areas that are front of mind for me. First, we’re focused on unlocking the full potential of our platform, which will set us up for the future as we scale and help us to be more responsive to our customers’ evolving needs.

Second, it’s about supporting our accounting and bookkeeping community to respond to this changing environment so they can continue to be the trusted advisor to small business. This includes being more customer centric, and focusing on how we can continually add value for them - like getting new features and product enhancements to areas that are most important - serve them better and faster, and increase their engagement with Xero. And finally, we’re enabling and driving innovation across our ecosystem app partners and payments attach. Xero data shows that Xero customers who use online invoice payments, like Stripe or GoCardless, get paid up to twice as fast than those who don’t use online invoice payments.

XU: Can you share your vision for the expansion of Xero’s events globally and the reason for only hosting events in Xero’s big countries every 2 years?


Our global communities are growing quickly, so we’re evolving our approach to Xerocon to ensure we stay connected not just with communities in our existing regions, but also with those in our emerging  regions across the globe. The new format means that Xerocon will be held in different cities across Xero’s key regions each year. There will be a focus on destination locations for partners to build their plans around to connect, collaborate and network with each other. We’re excited to be back in London and the US next year, so stay tuned for more.

Xero Roadshows also continue to be a crucial part of how we can stay connected with our partners and small businesses at a country level.

XU: To help our audience get to know you better, could you please share some insights about your background and experience? We’d love to hear about the key milestones in your career that have led you to this role and what motivates you to drive success?


As mentioned before, I come from a background of small business through my parents’ medical practice. It really had a long lasting effect on me, and helped inspire me to take a step into entrepreneurship. I started three companies, took one public, served as CEO of two others, served as president of StubHub, and advised some of the largest tech companies (Google, Amazon, and others).

I’ve now come full circle to run a global small business platform that helps improve the lives of small businesses and their advisors. Another thing I was attracted to at Xero was the opportunity to lead a global organisation whose passion for supporting small business aligns with mine. There’s so much potential when you look at our total addressable market for small business and early adoption rates of cloud accounting around the world, and I’m so excited to lead Xero into its next chapter.

I have long believed that in navigating their careers, people tend to look at risk and reward in the wrong way. People should stop over-weighting the first choice they make. As long as you are willing to keep choosing, there are a thousand choices between you and success. Keep aiming for impact in every single choice. As long as you keep working for what you want and without being afraid to fail, success will eventually come. Learning how to be agile and continually trying to succeed will lead you there vs trying to avoid risks overall.

XU: What are your observations about the values exhibited by the Xerocon community? How do you envision contributing to and fostering these values in your role as CEO?


Not too many people know, but I actually attended Xerocon Sydney last year when I was still in the process of interviewing for the CEO role. Attending Xerocon allowed me to see firsthand how our partners and the Xero team interacted at the event. I was just blown away by the mutual trust, respect and genuine love for Xero - it was actually one of the convincing factors for me to take on this role. And that’s exactly what I’m going to continue to make sure we show every time we get to immerse ourselves in this amazing community together - whether it be at Xerocon or any other events. As mentioned earlier, we want to continue to strengthen our already strong connection to our customers and I see trust, respect and love for our product as key to that.

XU: The success of Xero is undeniably driven by the hard work and dedication of the talented individuals who make up the Xero team. How do you perceive the importance of the Xero team in achieving the company’s goals and maintaining its competitive edge?


A lot of this comes down to the hard work and passion of our people at Xero. Xero is unique in that our culture is truly something special and Xeros - as we like to refer to ourselves - live and breathe our values everyday. Our desire as Xeros to listen to understand what challenges small businesses are facing, the dedication to creating and refining the best products to meet those challenges, and the overall passion for helping small businesses succeed is at the core of what makes Xero, Xero. Without the incredibly hard work, commitment to our purpose, human approach and willingness to challenge and innovate from our teams, we simply couldn’t do it.

XU: As Xero has expanded its reach globally, the company now operates with a widely dispersed team across various locations worldwide. What do you see as the primary challenges in managing a geographically diverse team, and how do you plan to address these challenges?


Just like any other global company, we’re always assessing how to ensure our teams can collaborate effectively across time zones. We trust our people to make the best decisions about how their team can best work together, whether that be through asynchronous communication or setting a regular meeting cadence - whether virtually or in person - that takes into consideration different time zones.

One small example is our monthly all company team meeting. Each month we host from a different country or office - for example, the July meeting was live from Toronto, and June was from Milton Keynes in the UK. We highly encourage our people to attend or watch it together in the office common spaces from wherever they are, as long as it’s within working hours. We also provide the recording afterwards for those who weren’t able to participate.

Our aim is to share important information, celebrate milestones and achievements and answer questions from our people all together as one global team - helping people feel connected across different time zones.

What unites us all though - regardless of role or location - is our commitment to our customers and our purpose to make life better for people in small business, their advisors and communities around the world.

XU: Could you share what particularly excites you about the next year, 2 years, and 5 years for Xero? What key milestones, initiatives, or market opportunities do you anticipate pursuing for continued growth?


I mentioned earlier the total addressable market being really significant - the opportunity to help drive cloud adoption across our key markets and to support even more small business customers is really what motivates me every day.  

We continue to be focused on taking the advantage of our long term opportunity and driving disciplined, customer-focused growth.

One thing I’m particularly excited about is our new Xero Beautiful Business Fund - this is a brand new initiative to help support the future growth ambitions of small businesses globally. We have more than NZ$750,000 total funding up for grabs and we’ve just opened the call for applications at Xerocon Sydney, so I would encourage all partners to get behind this and encourage your clients to apply, and you can even go in the draw for some great incentives by referring your clients.

XU: Could you share your perspective on the importance of the Xero community and the ecosystem of apps? How do you plan to foster and leverage this community to drive further innovation, enhance user experiences, and create value for Xero’s customers?


Our vision is to be the most trusted and insightful small business platform, and so it’s difficult to overstate just how important our wider community of more than 1,000 connected apps is to Xero and to Xero’s customers. Small businesses have a diverse range of needs and we believe that no single product or service can solve them all. Through our open platform, we enable others to create solutions to satisfy those needs, so we can deliver more value to Xero users and solve the wider needs of small businesses across the world.

We’re working hard to match-make our customers with the right apps, so they can see the benefits. As part of this, we launched the Xero App Store in 2021 to make it easier to find, try and connect to apps that integrate with Xero, and then last year we released the Xero App Launcher to help bring that experience directly into the Xero dashboard. This brings both our customers and our app partners closer together than ever before.

XU: We’d love to hear about a quote or piece of advice that has been particularly influential in shaping your leadership style or guiding your decision-making. Could you share any with us and how it has impacted your approach to leading teams and driving business success?


It’s crucial to build a professional tribe. These “professional priests” are people who know you professionally and personally and can help you to navigate your way, gut-check your decisions, provide different perspectives, ask the tough questions and help you define and ultimately achieve success.

Prioritise smaller actions rather than agonising over the big decisions

Always passively network: you never know when you’ll cross paths with a coworker or person in your network that can help you out

Don’t underestimate the value of a professional confidante, be that a coach or a peer at another company that may be in a similar point in their career – we all need a “professional priest,” to talk things through with in a safe space, who’s not our board or our spouse!

XU: In a rapidly evolving technology landscape, disruptions and shifts are common. How do you plan to adapt and future-proof Xero’s business strategy to stay ahead of emerging trends and maintain long-term success?


At our recent annual results call, I spoke a bit about how we reorientated the company for the next stage of Xero’s growth. We recognise that the technology sector and the needs of our customers are constantly changing, so it’s important that we be more flexible and responsive, and smarter about where we put our resources and focus.  

We announced that while we continue to be focused on delivering ongoing value for customers through our product and technology developments each year, while also continuing to invest in a multi-year platform modernisation strategy to unlock long term efficiency, scalability, productivity and speed to market improvements.

If we’re talking about leveraging emerging technologies like AI, Xero has always been excited about, and committed to, adopting new technologies to help our customers. As part of this, we’ve considered two key perspectives: 1) how AI will shape our products for the benefit of our customers, and 2) how AI will shape our company and the way our teams work. This enables us to be focused on where it can up-level our capabilities in a way that benefits our customers.

But we always have to balance the fact that accounting work often has a non-negotiable requirement to be financially accurate, and in some cases the consequences of inaccuracies can be severe. For example, a brilliantly worded but inaccurate tax return would not go over well with any country’s  tax department. So, when we think about our AI strategy, we need to take a strategic approach and look at how we can draw benefit from this technology, alongside managing the risks like factual inaccuracies that can occur with content generated with these models, while always considering our responsible data use commitments.

XU: Sustainability and responsible business practices have become increasingly important. What is your vision for Xero’s role in promoting environmental sustainability and corporate social responsibility?


Xero seeks to operate responsibly and contribute positively to the communities we serve. The really significant opportunity for us is in how we can help those communities - our customers and their advisors - to become more environmentally sustainable themselves. We’re excited about the ways the data in the Xero platform can be leveraged through third party apps to help them measure and reduce their carbon footprint.

XU: Innovation is crucial in the tech industry. What is your approach to fostering a culture of innovation within Xero, and how do you plan to encourage new ideas and technologies that can benefit Xero’s users?


The secret to true innovation is deeply knowing your customer. We set up our product teams around core “jobs to be done” and host a number of customer forums, events and advisory groups that helps us as a business connect with our customers in order to fully understand their needs. These conversations are critical in driving innovation and informing our data and product roadmaps.

Small businesses are very diverse, and to create new ideas that really serve them, we must prioritise diversity in our business. We have been recognised for our commitments in fostering a more inclusive and equitable workplace and consistently strive to improve this as we know that diversity of thought is core to innovation. During events we host, such as formal hackathons, we make sure that we include other parts of the business outside of just product and tech. This helps to ensure we have a broad mix of perspectives in the room. Ultimately, we know diversity always lends itself to better outcomes for customers.

Why leave it there?

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