In a fintech landscape thick with jargon and startup evangelism, Xero CEO Sukhinder Singh Cassidy cut through the noise at Money20/20 Europe with a keynote that was part product strategy memo, part leadership seminar and fully grounded in the realities of running a small business.

Joined by NALA founder Benjamin Fernandes, Cassidy laid out how automation and AI are reconfiguring SME finance not by replacing people, but by removing friction, sharpening insight, and restoring focus on the jobs that truly matter.

Asked what she would do differently if starting Xero today, Cassidy didn’t hesitate: "I’d begin by asking one prompt. One question that reveals the job the user wants to do."

In contrast to legacy workflows that presume the involvement of an accountant, Xero’s modern entry point would orient around intent, not process. That reorientation from a full-stack platform to a job-first experience is at the heart of how Cassidy believes software must now evolve.

“Cash in and cash out is the lifeblood of any company.”

Cassidy emphasized that small business owners don’t start with accounting, they start with survival. Before they even think about reconciling a ledger, they need to send an invoice, pay a bill, or understand whether they’ll make payroll. That’s the reality of operating with limited time and tighter margins.

This insight shapes Xero’s product philosophy: identify the most critical job first, and use that as the launchpad. In her words, “Think about platforms where you do one job deeply, then use agentic AI to get them to the next job.”

While AI was a predictable topic, Cassidy’s take avoided cliché. Three-quarters of Xero’s bank reconciliation already runs on machine learning, but the company hesitates to fully automate it because users still find satisfaction in seeing tasks resolved.

Instead, the future lies in the cycle between insight and action:

All of this, she stressed, must happen in a secure, compliant loop, especially when dealing with sensitive financial and tax data.

Cassidy also outlined where Xero is applying AI inside the company, with three high-impact areas:

Critically, she doesn’t expect her teams to reinvent the wheel: “You don’t need to invent everything. Be a fast follower, then scale.”

Automation doesn’t eliminate accounting. It upgrades it.

Cassidy believes AI will move accountants from task execution to strategic foresight:

And therein lies the real promise: helping small businesses move beyond today’s crisis and into tomorrow’s opportunity.

Cassidy pulled back the curtain on how Xero evaluates acquisitions using a strict matrix:

If a company doesn’t align with both, it’s off the table.

She highlighted the acquisition of Sift Analytics as a model deal: a benchmarking feature that served a clear sub-job, integrated directly into the Xero App Store, and instantly expanded value across 4.5M subscribers.

For founders hoping to be acquired, Cassidy’s advice was clear: “Show us how you lead in a critical sub-job and how your tech accelerates us 24–36 months ahead of where we could go alone.”

When asked what red flags she’s seen in potential acquisitions, Cassidy pointed to a common trap: roadmaps without focus.

“It’s fine to have a Chapter Two or Chapter Three,” she said. “But if your roadmap tries to be everything, we worry you’re chasing growth, not building it.”

Her advice to founders: narrate your trajectory. Show sequencing. Demonstrate that your product bets are prioritized, not scattered.

The session ended not on valuations or AI, but on something more personal.

Cassidy recalled growing up in Canada, helping her Tanzanian parents run a small medical practice. Each year, she and her sisters would sit with their father to manually enter every check and build a ledger by hand.

That muscle memory of reconciling line by line, of making sense of a year’s worth of trade-offs—stayed with her.

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