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Xero’s Jolly on building a tech roadmap to level playing field for small businesses
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Xero’s Jolly on building a tech roadmap to level playing field for small businesses

Xero’s Jolly on building a tech roadmap to level playing field for small businesses

Christine Hall·
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·Jan. 14, 2026·4 min read

It’s not just enterprise companies investing in AI for driving efficiency and lowering costs–but small businesses have a different set of considerations and hurdles for adoption

The analytics gap between large corporations and small businesses is getting wider. Enterprise-level companies have entire teams dedicated to calculating customer lifetime value, justifying big investments and crunching numbers to produce a constant stream of insight. These teams perform critical analyses that guide whether it’s worth buying a new delivery van or which customer segment to target for growth, ensuring every move is data-driven and strategic.

But for small business owners, these analytical luxuries can feel, and be, unattainable. Instead, these entrepreneurs are often forced to experiment with little information, making business-critical decisions based mainly on instinct and a patchwork of spreadsheets. 

Diya Jolly, chief product and technology officer at Xero, knows this struggle intimately — and it’s exactly the gap she and her team are determined to close in their work at the global company, which helps over 4 million small businesses perform accounting, payroll, and payments. Jolly, who joined Xero in 2023 as chief product officer, built her career in product roles at Google and Okta. It was at these technology powerhouses that she gained a strong customer mindset and learned how to gain enterprise-grade trust. 

But it’s her personal passion for empowering small businesses, many of which are owned by people in her own family, that drives her relentless focus at Xero.

“I tried running my own small business,” Diya said. “It was so hard, I gave up after four months. I just realized how lonely and burdensome it can be. So when the opportunity at Xero came, it was about making life easier for people just like my dad and sister.”

That empathy and mission filter down into every product decision Xero makes. Under Jolly’s leadership, the company is advancing a product philosophy that is not only customer-centric but also gives small businesses the same analytics power as the large companies. 

It’s a key factor driving the new AI-powered analytics capabilities Xero launched today that enables customers to access analytics, insights, and reporting, while also getting instant answers to their financial questions.

The analytics divide

The difference between the analytics capabilities accessible to large businesses and those available to SMBs is stark. 

As Jolly puts it, “Once you are a company with a few hundred people, there are a ton of people telling you where your business is at, how you should make decisions based on data, and what’s your cash flow. That’s not available to most small businesses without a lot of effort. They should be able to have the same benefits a big company has.”

This gap isn’t just about fancy graphs or dashboards either; it’s about survival. Between 30 and 50 percent of small businesses, depending on which country you are in, go bankrupt because of cash flow, Jolly said. And that’s not because the business is bad, but because money hasn’t come in yet and bills are due, she added.

Following its acquisition of Syft, an AI-powered reporting and insights platform, and bill-pay startup Melio, Xero worked for a year to perfect analytics features so that it can put enterprise-grade intelligence into the hands of small businesses. This includes customizable dashboards to view performance across various data, a cash flow manager, business health “scorecards” and insights driven by artificial intelligence.

“We’re bringing the power of business analytics to small businesses to help them flourish and grow,” she said.

AI for SMBs

The new analytics capabilities are also part of Xero’s broader AI and insights strategy that includes another recent tool called JAX, which is Xero’s AI financial superagent.

Imagine not having to chase down overdue payments, manually reconciling bank statements, or guessing which bills could be pushed longer. Automating such routine tasks can save the average small business 22 hours per month, Jolly said.

“When you come in, it tells you, ‘These are the things waiting for your attention; here’s what’s critical for your cash flow; here’s a customer payment to chase,” she said.  The goal is “a CFO, accountant, and analyst rolled into one, working for you 24/7.”

Xero has also put in guardrails to avoid errors — crucial for financial data — and an open ecosystem. For example, if you want to piecemeal Xero’s applications with those of another company’s, that’s no problem, according to Jolly..

“We’re not building a walled garden,” she said. “If you want to connect with other providers, take your data with you or use our analytics with third-party tools, you can. We always start with the customer’s needs, even if that means slower revenue growth or giving up control.”

The year of AI

Looking ahead, Jolly said 2026 is going to be “the year of AI” which will “remove busy work from enterprises, people, and small businesses” and then free up owners to make more intelligent decisions to grow their businesses.

Whether that’s benchmarking performance against local competitors, deciding when to purchase a new delivery van or simply staying afloat during tough times, the more artificial intelligence tools that are embedded in a platform, like Xero, the more people will start seeing the benefits, Jolly said.

“In a world where there are agents for this and agents for that, people are getting overwhelmed with having to stitch them together,” Jolly said. “What is unique to Xero is that JAX stitches all these agents together for you and orchestrates them for you. With an uptick in users of AI, people will start to trust it to do more and more.”

  • Christine Hall
    Christine Hall

    Christine Hall is a freelance journalist who previously wrote about enterprise/B2B, e-commerce, and foodtech for TechCrunch, and venture capital rounds for Crunchbase News. Based in Houston, Christine previously reported for the Houston Business Journal, the Texas Medical Center’s Pulse magazine, and Community Impact Newspaper. She has an undergraduate journalism degree from Murray State University and a graduate degree from The Ohio State University.

    View all posts
Tags
AI analytics for SMBsAI in accounting softwareDiya Jollyfinancial automationJAX AI assistantMelio acquisitionsmall business AIsmall business cash flowSyft acquisitionXero
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