Operator Spotlight
Technical & Product

Meet Xero Chief Product Officer Diya Jolly

Caroline Caswell

“How did they do that? How did they get there?” Companies succeed because of the people who build them - operating leaders who grow businesses to new heights and make decisions every day that can impact entire industries. Each month, our Operator Spotlight gives you the inside track from one of our incredible Operator LPs (Limited Partners) who are changing the game – building and scaling some of the world’s most successful companies. Read on for lessons learned and mistakes made, perspectives from the top, practical advice, and ideas on what’s next.

This month, we chatted with Diya Jolly, Chief Product Officer at Xero, where she is responsible for developing and launching consumer and business products in high growth small and medium-sized businesses. Prior to Xero, Diya served as the Chief Product Officer at Okta where she led the product innovation that has helped fuel the 4X growth in revenue over 4 years. Before Okta, she served as Vice President of Product at Google responsible for YouTube Monetization where she grew from 6X in 4 years. She currently sits on the board of ServiceTitan. Diya holds an MBA from Harvard Business School and a Bachelor of Electrical Engineering and Economics from the University of Michigan.

You’ve made the jump from larger enterprise companies to smaller, high growth companies - what have been some of the most impactful lessons from those moves?

DIYA: No matter what the size of the company, if you want to build successful products that are commercially viable  you need to be able to know and understand your customers and the markets you operate in deeply. Regardless of whether you are in a large or a small organization you need to set time aside for this or you get lost in the day to day. I follow a very rigorous process where I set time aside every two weeks to use my own product(s), talk to and even shadow customers, read up on the market landscape, technology changes and any new ideas that would make it easier for us to deliver better products that would delight our customers and provide them with more value.

Everyone who has worked in a big company knows that what you achieve is all about the team you built. Always hire people better than you is my motto. You will learn from them and they will have more impact than you ever could alone. This is even more true in a smaller company. In a large company you may be hiring many more people and a few stars can help carry the team. In a small company you only get a few hires. So you have to make doubly sure that they are A+ players.

Tell us a bit about your journey leading product for consumer, B2B, advertising, hardware, software (did we miss any?!) across incredible organizations. What have been some of the throughlines across your career?

DIYA: I’ve been lucky enough to get the opportunity to work on some really tough and interesting problems, be it for Google, Okta or Xero. The top three things I’ve learnt and applied in my career are:

  1. Whenever selecting a career listen to your gut and optimize for what you think you will love. I remember when I first told my father that I wanted to design and build products. He didn’t understand why I wouldn’t follow a more traditional career path. He tried to convince me to become an accountant or a lawyer. Later in life, my professor at business school thought that I should pursue a career in CPG and operations while my husband thought I should pursue marketing or corporate/ business development or finance. However, in my gut I knew that I really wanted to innovate and build new products that changed peoples lives. Despite everyone close to me thinking that I’d be better off in a different function/ industry I went with my gut. Today I love what I do and it doesn’t feel like a job. It is what has given me the ability to persist through the hard times and keep getting better and better at what I do.
  2. When selecting what job you should do, many  people optimize for brand name or what is “hot” (especially in tech) or the highest compensation they can get. While I have a lot of brand names on my resume I have never optimized for any of these criteria. I have always optimized for how I would learn and grow, who I would get to work with and finally what impact can I personally drive for the organization and for the world at large in a given role. This formula has served me really really well and I think it has been a large part of me being able to stand out to get more and more challenging opportunities.
  3. A friend of mine told me that she refused to accept a promotion to vice president at a very well regarded high tech company because she didn’t think she knew how to do all aspects of the job. She felt that she would be much better prepared in two years. I often hear a different version of this that says I’ll take more challenging roles when my kids are older or when I….. The reality is you will never be ready for the next challenge if it is a challenge that will truly stretch and grow you. And many times your refusal to take the opportunity is your fear of failure. However, growth only comes when you put yourself at risk and try to do something that you have never done before. I’ve faced situations multiple times in my career when I was sure that I could never do a role that I was being offered. However, every single time I took the role, put in the hard work and tried to learn from my mistakes. It was painful and humbling but it grew me faster than if I had waited to be ready for the next role.

There’s a lot of chatter about the impact of Generative AI in the developer field, how are you thinking about its application and the future of the industry?

DIYA: We’ve always been committed to innovating to help businesses streamline time consuming and manual processes, while delivering useful and timely insights to help them make more informed decisions. AI is a core technology that delivers on this commitment and already powers many of Xero’s products.

With Generative AI, we've been experimenting with how it can help our customers find the information they need through seamless conversational interfaces. Investing in GenAI was a straightforward decision: we're always looking to give our customers new ways to engage with our product and their finances.

More broadly, our approach to AI, is focused on four key areas:

  1. Helping customers reduce toil and run their businesses more efficiently and effectively by automating and streamlining repetitive, time-consuming work
  2. Delivering the right insights at the right time to help customers thrive
  3. Introducing conversational interfaces that can assist customers and improve their experience
  4. Increasing the productivity of our teams so they can deliver faster for our customers

What are some of the most important dynamics between engineering and product teams? How do you keep both aligned?

DIYA: A good product is equal parts mathematics and art. For example, the iPhone was not made by only mathematicians, it was also made by artists. So while engineering and product teams have their own dynamics, it's about channeling those dynamics into a common goal in mind and creating products and features that are relevant to our customers. Our best product and engineering teams combine technical understanding with a commercial acumen that allows them to understand how to create and build more value .

You have a fantastic view into how work products have evolved over the last two decades. What’s different about the space now vs when you started your career?

DIYA: I think there have been three seismic shifts since I started working 23 years ago.

  1. The ubiquity of the internet leading to cloud applications - When  I first started working you had to dial in via VPN to connect to the internet at snail speed. All applications were primarily desktop applications. Even email applications like Lotus Notes were not constantly connected to the internet. They had to “sync” to the internet. Today 5 minutes with a disruption in internet availability brings our work world to a stop. We can’t email, we can’t Slack and we can’t access any of our applications which are primarily all cloud applications
  2. Mobile phones become a core part of work - When I first started mobile phones were a novelty. Very few people had mobile phones and they were voice only phones that looked like bricks.  Can you imagine your work world today without checking your email or Slack a 100 times on your phone or needing to give feedback on that very important document while you are lounging on your couch after dinner? It’s hard to imagine our work life without being able to connect to and access information in seconds.
  3. The third seismic shift is something we are going through right now and is midstream. And it is the impact of Artificial intelligence

What are the most important traits you hire for when building out your product teams?

DIYA: Ownership mindset aside, I think one of the best qualities for a strong product team is having a healthy obsession with delivering measurable customer value while having the wherewithal to launch and iterate, rather than to wait for perfection. You cannot build something perfect on the first go, as you’ll never have enough information. Even the customers that are asking for a product don't know how they would use it until they start using it. So, it's better to put out a product that is reasonable, that can then be sharpened and tweaked over time to be made better.

And something to consider about customer value, is that it doesn’t only mean revenue. It can be an increase in customer satisfaction or a deepening of engagement with a product, but your product team must be clear on what the value is that you're looking to provide.

What’s a leadership lesson you experienced that surprised you?

DIYA: A pivotal moment early on in my career came during my time as a consultant at McKinsey. I had just jumped into the professional world as a 23-year-old, and my first couple of clients were relatively easy and lightweight. All of a sudden, though, I’m thrust into a situation with a client that was not at all receptive to guidance from a younger employee like myself.  

It wasn’t uncommon to hear comments like, "What the hell is a 23-year-old telling us?"

Meanwhile, the expectation was to go and win over the client regardless of their attitude. Really what kept me going was an unwillingness to say “no.” It wasn’t an option. I’d figure out a way to move forward and eventually I’d find a light at the end of the tunnel, and that I did. I have my 23-year-old self’s determination to thank since this trait of saying no has helped me out multiple times in my career especially when I’ve taken large leaps in roles to grow and have to rely on my grit to persist through.

How have you made a mark in your industry? What’s something you’ve done that’s perhaps counterintuitive in your field - broken any rules with interesting results?

DIYA: I’m really proud that over my product career I’ve been able to scale products that have both delighted millions of customers, while also being commercially viable. I’ve achieved this by constantly chasing learning and development, and being very curious.

To continue to grow and develop, sometimes it has meant following my own intuition and making decisions that don’t make sense to others. For example, I left a really safe and successful job at Microsoft to go to a small startup. Though many questioned it, that role gave me decades worth of experience in just a few short years, because of the tremendous amount of hats I wore. I did end up back working with enterprise tech at Okta, but then left to start my own business. Though I didn’t do that for long, that ended up being such an invaluable learning experience for me when I moved to small business accounting software Xero. It gave me a huge amount of empathy for our customers and the struggles they face every day.

What’s your secret super power?

DIYA: I’ve always been really good at absorbing large complex pieces of information and making sense of it. That has allowed me to cut through the noise and helps me focus my energy on what’s most important. I’ve also always had an innate sense at how product and tech innovation will unfold in the future. That ability to predict what technology to invest resources in, has helped bolster business innovation.

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