This Month in Fintech

AI, Automation, and the Future of Fintech Platforms with Diya Jolly

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We sit down with Xero’s CTO/CPO Diya Jolly to unpack how AI, product conviction, and human judgment are reshaping small business finance. From JAX, Xero’s financial superagent, to passwordless lessons at Okta, we dig into saving time, making better calls, and building faster.

• Xero vs QuickBooks and why orchestration matters
• Jax as a unified financial superagent
• Transparent automation that invites human override
• Data moats and domain depth as AI advantages
• Focus markets across ANZ, US and UK
• Auto bank reconciliation and 22 hours saved per month
• One leader across product and technology
• Reversible vs one-way-door decisions and speed
• Career jumps for learning over brand
• Betting on passwordless and proving security with less friction
• Google lessons on pairing data with intuition
• The next decade of fintech UX beyond dashboards

Connect with the Host & Guest

Sasha Pilch: https://www.linkedin.com/in/sasha-pilch

Diya Jolly: https://www.linkedin.com/in/diyajolly/


Welcome

Sasha Pilch

Hello and welcome to the listeners of the This Month in FinTech podcast. I'm so happy that you could all join us today. My name is Sasha Pilch, and I'm delighted to interview our guest today, Diya Jolly, Chief Technology Officer and Chief Product Officer of Xero. So, Diya, it's great to have you on the podcast. How are you today? Thank you for having me, Sasha. It's great to be here. And where in the world are you calling from today?

Diya Jolly

Um, I'm in the San Francisco Bay Area. Um, I usually am on a flight. I live on a flight, but uh today I happen to be here.

Sasha Pilch

When I was doing the preparation with your comms team, they were explaining that because Xero is a New Zealand headquartered APAC company, you're often on a flight to Australia. I'm actually Australian, so I know that flight too well and it's really long. So, do you have any hot tips for jet lag?

Diya Jolly

Hot tips for jet lag. Um, I am actually not that great at jet lag, except I do enjoy the flight because it is a flight at night. You can go to sleep, um, and then you can wake up and have a productive day.

Sasha Pilch

Yeah, true. There's no disruptions, like you're just in there for 17 hours. So it sounds good.

Diya Jolly

My hot tip for jet lag is just get through it.

Sasha Pilch

Yeah, just survive. Me too. Um, great.

Xero Vs QuickBooks: Big Picture

Sasha Pilch

So for the listeners that don't know, Xero is a multi-billion dollar public company and it's a leader in accounting and fintech software for small businesses globally. Um, I was actually the 13th employee of Rant back in 2020, and back then we only had two accounting integrations. We had Xero and we had QuickBooks. Later, we added Sage and NetSuite as our customers started to grow and had those needs, and we went upmarket with customers. But I'd love to talk about how Xero fits into the space now in 2026. So, for those listeners that are thinking about deciding between Xero and QuickBooks, what are the differences? What's the strength?

Diya Jolly

Yeah, absolutely, that's a great question. Um, because from the outside it all sounds like it's the same thing.

JAX: The Financial Superagent

Diya Jolly

So Xero really fundamentally today, in today's world, if you think about Xero, um most software platforms are being changed dramatically because of AI and automation, right? And we're no different. We believe we can deliver a lot more value to our customers than our small businesses via using new technologies out there in the market. Now, a lot of companies are automating um and providing individual agents to customers, and they then have to stitch all of this stuff together. We, on the other hand, believe that you as a customer don't have the time to do this, right? Like you need someone, the reason you come by software is so that someone can actually stitch everything together for you. So we have this concept, our our concept of a financial superagent, which essentially orchestrates all your other agents for you. Um and we call it JAX. The reason we call it JAX is because we think of it as your personal financial assistant. And with that personal financial assistant, you can talk to it just like you talk to any other employee in your company, and it does all the tasks that you need it to do. Um uh and you don't have to go talk to um a um uh bookkeeping agent or a payroll agent or a payments agent or a bill pay agent. Um so we simplify it in that way. So that's one thing. I think the second place we're very different from most other SaaS companies is we are um we believe that um most domains um like that that small businesses and and um uh CFOs and accountants and bookkeepers um work in required some element of human judgment. Some of it is a lot of it is automatable, but at the end of the day, human beings are human beings because of their judgment. So the way we build our products or all our AI and automation product is to make it easy for a human being, make it transparent to a human being what what has happened with the automation, why it has happened, and also make it easy for the human judgment to be applied as and where needed. So we'll either solicit the human judgment if there's human judgment needed, or we'll also um take in the human judgment of the human if the human being wants to override something. And it's built with that, it's

Human Judgment In An AI World

Diya Jolly

built with that mindset, which is it's not just automated workflows, it's automated workflows that makes human beings better.

Sasha Pilch

That's an excellent example of how you're utilizing AI to improve the product. And I can see that other players in the market are also trying to make the use of AI as everyone is in 2026. What about your thoughts on newer, yet smaller entrants to the market? Um, Rillet, for example, founded by Nicolas Kopp, who a lot of our audience knows because he was the CEO of N26 when that launched in the US. Campfire is another one that comes to mind. Anything you'd have to say about how you differentiate there?

Diya Jolly

Yeah, so look, I think um we're always watching others in the space and and we're always learning from other people. Um, what we have that is differentiated is a couple of things. We have uh four and a half million subscribers using the platform. And in the world of AI, data is king. So um the more data you have and the more data you can um uh build agents on for your customers, uh, the the more complex agents you can build and the more um accurate they will be. Uh the other thing is we also have domain knowledge, deep, deep years of domain knowledge, right? And that also helps you shape agents uh much more deeply. Because think about this. The reason you don't go to a horizontal

New Challengers And Data Advantage

Diya Jolly

LLM like a chat GPT to do your uh accounting and bookkeeping is because the rules are complex. Even for LLMs, the rules are complex and there is judgment required in the rules. Um we have four and a half million customers that have been using us forever, have been telling us what judgment they are taking. So we have all of that data to build on. Um, and then the other thing um I would say is it's actually funny. I tried to start uh my own uh my own bookkeeping slash payments type company after I left Okta. And I quickly realized that, oh, I uh and AI had just LLMs had just come out, and I'm like, we should be able to use this to turn everything around. And I quickly realized data is a huge advantage in the space. So I'd say that's really how we think about it. How do we learn from people who are using it, our customers, and then how do we use AI to make that better?

Sasha Pilch

Exactly. Yeah, and especially with LLMs learning with all of the data and experience that they've had as an import. So it makes total sense as to why Xero is a leader. And you're definitely a leader in regions like APAC, you know, you're founded in New Zealand. Can you talk to me a little bit about what's next for the regions that you're going to tackle and be the dominant player in?

Diya Jolly

Yeah, absolutely. So look, I think um what Xero has been known for is um its customer centricity and its really simple and easy-to-use interface in all the countries that we're in. Um it's easy to use, yes, yet it's a end-to-end fulfilled uh full uh uh it's an end-to-end complete financial platform with uh bookkeeping, uh tax, uh, and compliance, payments and payroll. Um when you think about what's uh what is uh what we're looking at in the future, it's a few things. Look, our customers' needs do keep

Market Focus And Product Depth

Diya Jolly

deepening and changing. So we've said we are going to focus on um three key markets, which is Australia Um and New Zealand, U, US and UK, right? And really it's not that we can stop building customers need more things, regulations change, new forms of paying people come out. So uh payroll, uh in payroll uh more innovation happens. So, how do we keep deepening for our customer needs set and um expanding expanding the types of customers we can serve to some some extent, right? We're we are very good in certain sex segments and verticals. There are other segments and verticals we can therefore. Uh but I think that is one aspect of it. I think the other aspect of it just is can you just rethink software right now with with all that's happening, right? And and this is where I talked about a bunch of uh this is where I talked about this is this is what I was referring to when I talked about um AI changing how software works. So um rethinking what software means and how much more value it can deliver to our small businesses.

Time Back: Auto Reconciliation

Diya Jolly

Um, for example, we just launched uh Autobank Reconciliation, and that saves customers 22 hours per month. That's four to five hours per week. That's five, yeah, five hours per week. That's crazy. That's huge. Think about these small businesses or accountants or bookkeepers who are so time-strapped, right? So now you can bring technology to bear that actually gives them time back, whether they want to use it for growing their business, whether they want to use it for other things. It gives them like their evenings, their weekends back. So that I think that is what the next uh generation of innovation would be around.

Sasha Pilch

Excellent. So important for these small businesses to have time back in their day.

One Leader For Product And Tech

Sasha Pilch

And with you talking about these priorities for zero, it's probably a good segue to talk about the dual role that you have as both chief product officer and chief technology officer. How did this come about and how do you what's your secret to time management?

Diya Jolly

Um how did this come about? I actually think the world is moving more and more to a combined role, to be honest. Um, and the reason is because uh if you have one person that can arbitrate, if you have one person that understands both, it reduces a lot of the friction. And then if you can have one person that arbitrates across um what to build and how to build it, it just makes decisions move faster in the org. It uh makes spinning happen less, like when when uh different teams spin. Um and it just I think leads to a better outcome. Uh the trick though is you need to have a product leader who's quite technical, and you need to have it, or you need to have a technical leader who's very customer and pro who is very customer and product focused. So, but I think as time goes on, as AI is making it easier to write applications, it's not making it easier to write every kind of software, but it is making it easier to write applications. I think you will see more and more of the combined role. Um in terms of time management, honestly, I think there are there are a few different frameworks or a few different things. One is like I'm blessed that I have an absolutely amazing team, right? Um and uh so they they're the ones that really do a lot of the work. Um I think the second thing is um I keep my focus on the top three or four things. My my um I decide at the start of every week what are the three things that I'm gonna absolutely do

Decision Speed And Reversible Bets

Diya Jolly

this week that are most important to move the business. Um and then I have it at a month level, I have it at a weekly level. And so I make sure I have time blocked out on my calendar for that. And then the other thing is not spending too much time making a decision that is reversible. Sometimes it is better if a decision is reversible, if it's a two-door, two-way decision, then moving faster is better than um continuing to debate it and spend time. If it's a one-way door, then you need to spend the time and the effort. Um, but even in a one-way door, can you construct it, can you get your team to construct experiments that give you an early signal so you don't end up spending all the like spending too much time spending on it?

Sasha Pilch

I totally agree. And the fact that you have this dual role of CTO and CPO does make so much sense, especially as the organization grows. There's no these two silos of two leaders working on their own top three things, which might be different things. So it makes total sense that you're the leader across both of those orgs. So, like, I love to hear it. Um, and it's probably a good segue to talk about how you got to this point.

Career Jumps And Learning First

Sasha Pilch

So, your earlier career. So, you started at McKinse on the grad program, and you then went to Microsoft where you led bringing live TV to Xbox. In 2008, you joined a pre-revenue startup called Free Will, which you successfully scaled and sold to Comcast. We've got a lot of listeners that are either working for a very early stage company or working for a large corporate and thinking about making the jump to a startup. So we'd love your insights on that experience.

Diya Jolly

Uh sure. So I I was relatively early in my career. I was part of a team uh that scaled it. Um I think the founders of that company get a lot of credit for scaling and and and uh selling it. Um I think the way I would think about decisions in your career, very early in my career, I made a choice to always chase learning and growth. Uh, not brand names, not what's hot, but learning and growth. Um I actually had a I had a uh role outside uh once I graduated from business school from one of the uh hottest uh companies in the Bay Area. I'll leave them nameless, and um I decided not to take it because the role that they were giving me uh just did not have the I just didn't think I would learn. Um and instead went to Microsoft. Um so I think that is one thing. I think in terms of, I believe you should jump across companies of different sizes and domains. If you look at my background, most people are either B2B people or B2C people or they are fintech people or they are uh consumer, like consumer platform people. I've always jumped around because I believe that different domains have learning for for across each other. Um so so from a from a if if you're thinking about your career and your early stage, what I would say is seek out experiences

Betting On Passwordless At Okta

Diya Jolly

where you can learn both from the content of the role as well as the people around you, and constantly put yourselves in roles that make you uncomfortable where you think you're gonna fail.

Sasha Pilch

I think that's excellent advice. It's scary advice, but I'm a big believer in doing the thing that scares you most because that's always gonna be the right decision if it's a calculated risk. Yes. Um 2019, um, you made a move to Okta. So and it was also the rise to your first C-suite position. Um as chief product officer of Okta. During your tenure of Okta, the company grew from 400 million to 1.8 billion over four consecutive years of achieving rule of 40 by launching innovative industry-leading new products like FastPass, Next Gen Identity. What a success story. So I first used Okta myself in 2019 when Quovo had just been acquired by Plaid, and the New York City employees were flown over to San Francisco for induction, and we were exposed to how the San Francisco office did everything. And I remember being blown away about how seamless the product was. So, can you share a little bit about anything that was pivotable in enabling your team to build such a futuristic experience?

Diya Jolly

Uh, that's a great question. I think uh, first of all, um the uh it's actually an interesting story. Um when I started at Okta, there was a lot of talk about passwordless, which is essentially FastPass. But the industry was like, will it happen? Will it not happen? Will it happen? Will it not happen? Right. And Okta itself was like, I have this whole laundry list

Proving Security With Less Friction

Diya Jolly

of things that customers want. Like my team was like, I have this whole laundry list of things that customers want from us. We know this is a short bet. This is definitely gonna happen. So should we spend time on that? That's so hard to do, it'll take away from all of these. So I think really the the the lesson here is you're not always um building a product is part science, but part art, right? And part part uh data and part uh and logic and part gut. Um so really what the team and I went with there was gut, right? Which is they if you cannot enter passwords, it increase it it reduces the friction to sign in, it makes signing in a great experience, it makes um actually makes security go up. So we made a bet that the world will definitely go in that direction, right? In terms of making it so you so you have to have some conviction to make up bets, because otherwise you will only increase your product incrementally. And now, will all bets win? Not always, uh, and that's where you need to be careful about spending enough

Lessons From Google’s Innovation Culture

Diya Jolly

resources on things that will win and spending and enough on new innovative bets. In terms of bringing the future a frictionless experience, I think one uh some of the lessons there are to get a team to understand the customer pain points, they must live the day-to-day of a customer. Uh you the team must unite on a on a common mission. So, how do you do that? You build a vision together and a mission together, and then you talk about it, and you talk about it, and you talk about it till it becomes second nature. And then really, a lot of teams get stuck in, I am going to wait till I have the perfect product. It took three years for I'd say to get fast pass to perfection, right? And and probably after, like, and after I left. So keep iterating, launch the first thing. You you can have a vision that you want to get to, but then don't get blocked by trying to launch your holistic vision. Break it up into simple steps that you can launch for customers, learn from them and iterate. Because I guarantee you, no matter what your vision was, your customers are going to tell you what it really needs to be.

Sasha Pilch

And such great advice. Like when I worked for big banks, I used to see millions, billions of dollars be put into products that were built in a silo and then they launched it to the market, and then no one wanted it. Or so I am a big believer in this like fail fast, fail often, test and learn. But the really like key point that you mentioned, which was not having to enter a password is less friction. But then there's that you know paradigm of do we increase friction to decrease fraud? So was that one of the things that you proved with the fast iteration that actually not having to enter a password is safer, even though it's less

Book Picks: Geopolitics And Metrics

Sasha Pilch

friction? Exactly.

Diya Jolly

That's a very, very good question. Um Are you sure you weren't in the security industry at some point? Um so yes, I think the hypothesis was uh biometrics or your fingerprint or your face ID is inherently harder to harder to fish, right? It's inherently harder to copy, uh, but it needed to be proven. And so the hypothesis was it's frictionless and it has higher security. And so as you rolled it out, there are a lot of companies that would be like, well, we're not sure, we still want a password. Uh a passphrase is more is more secure. Um, but then they would do rollouts and tests because we because it was designed in a way where you did not have to roll it out to everybody. You could do a test on a small cohort of people.

Sasha Pilch

And then the data spoke for itself and you your hypothesis is proven. Exactly. Um I I've just realized I've skipped over a big chunk of your career, which I'm actually very excited to double-click on. So you spent eight years at Google's Mountain View office. What was that like in that heyday of Google? Like, do you have any stories from Google that you're okay to share?

Diya Jolly

Um, heyday of Google. Yeah, I mean, Google was an amazing experience. I I all I generally say I grew up at Google and learned most of what I what I learned in product leadership um in the innovative part of product leadership at Google. I learned a lot on business discipline after as well. Um I think uh really the things that I that that I learned was like, how do you actually think about the customer? Put yourself at the center of the customer. How do you use both data? Because Google has a ton of data, but also data doesn't always tell you. What somebody wants because they who would have imagined, like,

The Next Decade Of Fintech UX

Diya Jolly

if you told me I'm going to chat into a chat box six years ago, I'd be like, what are you talking about? Um, so often you don't like it's it's the coming together of technology, intuition, and data that really tells you what customers can do. Um and getting the reps to do this at with a with people that are like world class at this at scale and innovating with them at scale. That is, that is what Google was. It was a startup, it was like a startup, even if, even though it was gigantic. Um stories. I think I don't have stories, but I'd say some of my closest prof, most of my closest professional friends to date, I've now been out of zero or out of Google for seven years. I was there for eight years. They're still people from Google. They're still my closest friends. So it was a it was a very tight-knit community uh that really helped uh that really just that really just thrived on innovation and launching and launching things people that that solved people's pain points.

Sasha Pilch

It's so special when that happens, like when you're really in flow state and enjoying your job so much that those people become your best friends. Like uh, I still have some of my best friends from Kovo and Plaid, they're coming to my 40th this year. So um I'm I feel really grateful that I got that experience, and it sounds like you you had a great experience at Google too, which is lovely. Um, we are kind of coming up on our time together. So I wanted to ask you a bit of a fun question. What are your favorite books? So personal, and it can be fiction or non-fiction, and a professional one?

Diya Jolly

That's a good question. Um so on on personal, I would say uh it still is. I was trying to see if if I've used this a few times, but I was trying to see if anything else um if

Closing

Diya Jolly

I if anything else would um would take its place. But there's a book called The Accidental Superpower that talks about how the US came to be um came to be uh uh the country it was, uh, with the amount of innovation, with the amount of um uh uh uh uh uh wealth creation, to be honest. And um I don't think I had ever thought about how geography uh impacts uh the destiny of a nation. Um and that is what it talks about, um, primarily, which is how geography and then the people that gravitated towards that geography is really what led the US to be the US. And so that that was a very intellectually interesting book that has nothing to do with the world I live in. Um on the professional side, um there are two books. I'll pick one um because I can't remember the name of the other, but it is it is um uh really the the power of mathematical thinking, right? Which is when things are ambiguous, when you don't know what decision to make, how can you put um how can you put measurement um to help guide you? So for example, right now we are trying, we are, we have, we're trying to figure out if we want to um make a decision about building a certain product. And there are about as many opinions on whether we should build it or not build it as there are our team members, to be honest. And so in a situation like that, how do you actually go, okay, here is the here's the metrics we want to meet, and then what is the smallest possible experiments that lead to understanding if those metrics are correct or not? That's really kind of along the lines of what that book explains.

Sasha Pilch

I think that's one of the reasons why I'm living here in the US rather than all the way over in Australia. Um, but yeah, definitely interested to learn more about that. So thanks, Diya, for sharing those. Okay, so we're nearly at the end. Is there anything that you want to share with the audience before we wrap up?

Diya Jolly

Um I would say the following. For anyone that is thinking about being in the fintech industry, for anyone that is thinking about building products or using products in this in the in the in over the next 10 years, um, I think where the world is going to go to, or I believe where the world is going to go to, I feel pretty confident about this, is that software will start doing more and more for you and will start becoming more and more of your um uh uh of your junior assistant. This is not revolutionary, revolutionary, uh, but um what will happen is that users will want an interconnected experience. They will not want um they will not want a ton of software all over the place, they will not want a ton of agents all over the place. So what you will see is, especially in FinTech, you will see the the financial stacks begin to collapse and and financial horizontals beginning to come up, and you're already seeing this, seeing this. I mean, this is one of the reasons we um acquired Milio is because we felt um you can't be a financial platform of the future without without um actually having bill pay and having the best bill pay capabilities. Uh the other thing I think you'll see is that um you not only is software helping you do stuff, it is also helping make it making it easier for you to get more intelligent. And what I mean by that is um it'll proactively start surfacing things like, hey, your cash flow is low, you should do X, or um uh have you thought about this business opportunity, et cetera. And then the final one, and this is my this is I'd say this is my belief, is um you're not just gonna experience financial products within a financial UI anymore. So what LLMs have done is it's made us be able to converse to software kind of like we converse to human beings. So why can't I converse with zero over text? Why can't I converse with zero over WhatsApp? Why can't I be in my Gmail and send zero an email asking it what to do? Um so I think you're gonna see more and more federated um uh software experiences uh from software products that may not be in their existing UI.

Sasha Pilch

I think that's great because there are so many times in our you know life right now where we're like, oh, I have to get back to you when I'm at my keyboard. But why? Like that's just slowing things down when it could be a pure, like a very um ubiquitous experience. So I'm excited for that. That sounds great. Okay, well, we're at time now, so I'm thrilled to have had you on the podcast, Tia. Thank you so much. It's been wonderful getting to know you. You've got a very inspiring story. Um, and to our listeners, you can find us wherever you get your podcasts. Please give us a review or subscribe. We'd be so grateful for that. Okay, thanks everyone. See you next month.