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Inspirational Women Leaders Of Tech: Diya Jolly Of Xero On The 5 Steps Needed To Create Great Tech…

Inspirational Women Leaders Of Tech: Diya Jolly Of Xero On The 5 Steps Needed To Create Great Tech Products

An Interview With Rachel Kline

Understand the problems being experienced by your target customer audience. What isn’t working for them today? This will help build your product’s hook, which you can then zero in on and build the right product to address that hook better than any competitor in the marketplace. Maintaining this “startup mindset” of identifying a gap and seizing it will help make your products as relevant and focused as possible.

Currently, only about 1 in 4 employees in the tech industry is a woman. So what does it take to create a successful career as a woman in Tech? In this interview series called Lessons From Inspirational Women Leaders in Tech, we are talking to successful women leaders in the tech industry to share stories and insights about what they did to lead successful careers. We also discuss the steps needed to create a great tech product. As part of this series, I had the distinct pleasure of interviewing Diya Jolly.

Diya leads Xero’s product and tech teams driving product management, development, design, and product marketing to further improve Xero’s global small business platform for partners and small businesses. Diya has market-leading global experience in designing, developing and launching consumer and business products in high growth mid sized companies, startups and Fortune 500 brands. Before joining Xero in 2023, Diya was Chief Product Officer at Okta where she led product innovation for both its workforce and customer identity business. Prior to that she was Vice President of Product Management at Google, where she was focused on driving adoption for some of the company’s leading products. Diya has a Masters of Business Administration from Harvard Business School and a Bachelor of Electrical Engineering and Economics from the University of Michigan.

Thank you so much for joining us in this interview series! Before diving in, our readers would love to learn more about you. Can you tell us a story about what brought you to this specific career path?

I’ve been in product for over 20 years, starting my career as a product manager at Microsoft and then going on to lead global product teams at companies like Google and Okta. But when I was growing up, I used to help my dad in his biomedical business in India. He wanted to bring cheaper healthcare to villages. I remember listening to his conversations about product design and commercial strategy, and realizing what an impact he was having on the world. I remember the exact moment where I thought: I want to think like that. I want to do that.

On the weekends and over the summer, I’d help my dad enter his accounting data into a software system called TALLY — it was on one of those 8-inch floppy discs. Remember those? My dad told me how this saved his team so much time. Funnily enough, 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.

It has been said that our mistakes can sometimes be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I think one of my first big mistakes, which is funny in a sort of tragic way, was trying to perfect the design and definition of a product for so long without anticipating what would really matter to our users when the product launched. This product was TV over internet. To be more specific, we were essentially trying to launch an IP TV experience, and we were trying to perfect a transition for the user interface to go back and forth between being clickable on a mouse while also being clickable on a remote.

We toiled over so many minute details and spent so much time on this specific piece of the product, but when it came time for a wider user base to interact with the product, this wasn’t even a function that saw much attention. Trying to perfect such a particular thing that ended up being a waste of time really taught me to streamline the design process for products and get a better understanding of what our customers will care about in a new product — honing in on (and obsessing over) customer pain points is much more productive and valuable at the end of the day. And while it may be more common these days, using iterative launch strategies with semi-open alpha and beta testing stages can deliver much-needed feedback before a product is finalized for launch.

What do you feel has been your ‘career-defining’ moment? We’d love to hear the lead-up, what happened, and the impact it had on your life.

To continue to grow and develop, sometimes it has meant following my own intuition and making decisions that don’t make sense to others. One significant moment for me in this regard was when I left a really safe and successful job at Microsoft to go to a small startup. Though many questioned it, I felt it was right and would get me out of the comfort zone I’d built for myself in this more secure and structured role. That time at a startup ended up giving 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 with Xero. It gave me a huge amount of empathy for our customers and the struggles they face every day.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

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.

Ok, super. Thank you for all that. Let’s shift to the main focus of our interview. We’d love to learn a bit about your company. What is the pain point that your company is helping to address? How does your company help people?

Xero is a global small business platform, which provides small business owners (as well as the accountants and bookkeepers that serve them) with accounting software and invaluable digital tools to support the many tasks that businesses have (such as payroll, expenses, payments, inventory etc) and streamline financial and operational workflows. It provides these entrepreneurs with capabilities that otherwise may only be accessible to larger corporations.

In a business ecosystem that often leads to high financial risk and potential for burnout, Xero helps automate much of the tedium, makes it easier to track performance and connects business owners with their banks and advisors in a much more seamless way so that they can truly focus their time and energy on being innovative and building a successful business.

If someone wants to lead a great company and create great products, what is the most important quality (for example, “determination” or “eye for detail”) that person should have, and what habits or behaviors would you suggest for honing that particular quality?

To build high performing teams in a successful company, the first thing a leader needs to do is make sure their direction is clear. Where are you headed and why? Why are you trying to accomplish what you’re trying to accomplish?

Communication skills are a non-negotiable. A great leader in the product world needs to be able to communicate their direction and purpose in a manner that other people understand. You need to be able to set clear and measurable goals around this purpose, and then be able to hold your team accountable to meeting those goals.

But holding your teams accountable by itself is not enough. You need to hire the right people, and this doesn’t just mean looking at a candidate’s skillset. It means looking for people that want to push boundaries, but also have a high emotional intelligence (the EQ to your IQ). Once you find those star players for your team, you need to be able to empower them and support them — retention is just as important as recruitment.

Next, let’s talk about teams. What’s a team management strategy or framework that you’ve found to be exceptionally useful for the product development process?

I am a big believer in establishing a framework for apprenticeship, particularly for the soft skills of product development. In my opinion, you need about 15–20% of people in your organizational model to be at the pinnacle of positive “behavior.” You then reward that behavior, and everybody else learns to figure it out and follows suit. To put this in more concrete terms, I think it’s super hard to teach something like an ownership mindset. I think you have to see it in action, whether from a peer, your manager or your manager’s manager. Having someone who already has this quality walk you through a problem and seeing how they navigate the situation is immensely more impactful and long-lasting than something a training course can provide.

When a product team is fully removed from the “not my problem” mindset, and everyone works as a unit to tackle challenges proactively, you’ve found the ideal framework. Anything can be built from this cornerstone.

When you think of the strongest team you’ve ever worked with, why do you think the team worked so well together, and can you recall an anecdote that illustrates the dynamic?

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.

Altogether, this is a quality that I think leading tech companies have which enables them to continuously innovate and launch incredibly successful products over time. It’s a cultural pillar and a muscle that needs to be built over time. Rarely does a business get this right from the jump, but you see it entrenched in longstanding tech companies.

If you had only one software tool in your arsenal, what would it be, why, and what other tools (software or tangible items) do you consider to be mission-critical?

I don’t think you need anything fancy to succeed in this sense. Communication is the one thing any team (product or otherwise) can’t live without. Email, text, and calls are the tools I rely on most to make sure we’re building great products, because without them, it’d be much harder to get my vision and my goals across to my team and to the broader organization.

Let’s talk about downtime. What’s your go-to practice or ritual for preventing burnout?

I have learned (perhaps the hard way) that there is a productivity curve, which means after a certain amount of time spent working, you’re just not being productive. My time in consulting was a perfect example of this — I could sit there for hours not being productive, but as long as I put my “face time” in at the office, I was seen as a good worker. Over time, I learned there are certain things that are just not productive, and spending 70+ hours working is one of them. While it may feel like you’re working hard by putting all this time into your work, you’re sacrificing valuable personal time that helps balance and foster the creative side of your brain that helps you bring ideas to the table at work.

So, in my downtime — what do I do? I dedicate as much time as I can to family and being there for my son. I like to maintain a healthy social life, exercise, meditate and (of course) sleep. All things that are essential for keeping your brain from short-circuiting and helping you have a clear head when you clock in.

Thank you for all of that. Here is the main question of our interview. Based on your experience, what are your “5 Steps Needed to Create Great Tech Products”?

  1. Keep an eye on the tech industry at large — stay informed and identify trends as they materialize. Understanding which trends can directly benefit your business and customers is a valuable attribute, and this is often the catalyst for emerging technology products.
  2. Understand the problems being experienced by your target customer audience. What isn’t working for them today? This will help build your product’s hook, which you can then zero in on and build the right product to address that hook better than any competitor in the marketplace. Maintaining this “startup mindset” of identifying a gap and seizing it will help make your products as relevant and focused as possible.
  3. Approach your new product idea with the combined mindset of a mathematician and an artist. What does this mean? You need to be able to understand your customers’ pain points from a business perspective, but you need to understand it from a standpoint of building experiences. The iPhone wasn’t built as a soulless machine of pure functionality. It was built with the knowledge that it would be the key to a brand-new universe for customers to unlock the expansive worlds of digital communication, entertainment and so much more.
  4. Synchronize with your engineering team. All roads lead back to the need for effective communication, and aligning with the people building the product is needed to ensure your goals are being met while maintaining expectations for what’s practical and realistic rather than being brainstorm fodder.
  5. Make sure your product is commercially viable. It’s the true test for a product in our economic framework. No matter how valuable it may be for your customers, a new product needs to be commercially viable. This is where balance is once again needed from a product team — know how to juggle your role as a customer whisperer, an engineering liaison, a creative problem solver and a savvy business person all in one.

Are you currently satisfied with the status quo regarding women in Tech? What specific changes do you think are needed to change the status quo?

No — I’m not satisfied. We are still far off from the amount of women leaders that should be in the technology space, even if some aspects have improved greatly. While women now outnumber men in the college-educated workforce, there is still a glaring need for more women in decision-making roles for the tech industry. There are many things that might keep that number down today, like unconscious bias (especially with perceptions of authority and aggression in asking for what they want, be that a raise, promotion, or some other form of recognition) and exclusion from networking opportunities that may have been historically male-dominated. Making sure these opportunities are available to the women leaders of tomorrow is vital, and it’s on us today to bridge that gap.

We are very blessed that very prominent leaders read this column. Is there a person in the world or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them 🙂

Yes! Satya Nadella — the best combination of product innovation, business acumen and leadership skills while still being a great, humble and transparent human being.

Thank you so much for this. This was very inspirational, and we wish you only continued success!


Inspirational Women Leaders Of Tech: Diya Jolly Of Xero On The 5 Steps Needed To Create Great Tech… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.

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