Guesty is a global software platform that helps property managers and hospitality businesses manage short-term rentals. With more than 20 global entities and seven acquisitions over a three-and-a-half-year period, the company’s rapid growth brought increasing complexity to its financial operations.
Since 2022, Barry Lin, Director of FP&A at Guesty, has used Datarails to automate budgeting, reporting, and consolidation while continuing to work in spreadsheets. Now, with the FinanceOS AI Connector, he’s taking the next step: connecting Guesty’s governed financial data to AI and exploring new possibilities for FP&A.
Getting FP&A Under Control
When Guesty first turned to Datarails in 2022, its growing financial complexity was putting a strain on FP&A. Budgets spanned departments, business units, and subsidiaries, while information from NetSuite and other systems had to be consolidated manually.
We relied on a gigantic Google Sheet to manage our finances, which required manual updates and calculations. It was a lot of manual work and was very difficult.
Preparing monthly reports could take up to two days. With Datarails, Barry could automate consolidation, budgeting, and reporting while preserving the flexibility of spreadsheets. A simple refresh replaced manual preparation, saving the team hours, sometimes days, during month-end close. He could also build and maintain Guesty’s budgeting infrastructure himself, without external consultants.
Beyond time savings, Datarails dashboards and drill-down capabilities gave Barry a more complete view of the business, including budgets, actuals, expense trends, and approved but unpaid purchase orders. With greater visibility into the numbers, he could investigate changes, spot issues earlier, and provide management with more detailed financial insights.
And with less time spent preparing reports, Barry could focus on work that had previously been out of reach.
I have so much more time now. I’m finally able to do things I couldn’t even consider doing before.
An FP&A Expert’s Introduction to AI
Barry knew his way around FP&A, but AI was another story.
I’m a finance person. I don’t consider myself a tech or AI person. Until recently, I was using AI a little bit like Google, asking questions, getting advice, maybe uploading a spreadsheet to analyze.
That changed when he started using Datarails’ FinanceOS AI Connector, which connects his mapped and governed financial data to external AI tools like Claude.
Barry had never used Claude before and knew little about how AI connections worked or how to build AI agents. But he didn’t have to figure it out alone.
I had three or four sessions with the Datarails team. They taught me everything from scratch: how to connect Claude with Datarails, how to connect it with Gmail, Slack, everything, and how to build agents.
With hands-on guidance from the team, Barry built specialized agents for FP&A, strategy, coding, and personal assistance, each with its own purpose and business context.
Datarails taught me how to explain what I’m doing, what my company does, what the agents’ purposes are, and how to build skills. I even got an exercise tailored to my data that taught me how to write prompts and pull financial data, headcount data, and budget versus actuals.
The sessions gave Barry more than technical knowledge. They changed his understanding of what AI could make possible in his own work.
I learned a lot, and I finally understood how powerful AI could be. I hadn’t realized that before.
Claude has since become Barry’s preferred AI tool at work, not simply because of what Claude can do, but because the FinanceOS AI Connector connects it to Guesty’s up-to-date, governed financial data.
I mainly use Claude because of the connection to Datarails. That’s where I have all my financial data, headcount, budgets, and forecasts.
And embracing AI hasn’t meant leaving spreadsheets behind. Barry can generate spreadsheets with Claude and publish them through Datarails as web dashboards, incorporating AI into the reporting processes he already uses.
One Financial Foundation, Endless Possibilities
With specialized agents, connected financial information, and new AI skills, Barry is beginning to rethink the way he approaches FP&A.
Barry is now exploring how AI can support more of his FP&A work, including workflows related to month-end close. Rather than simply automating individual tasks, he’s looking at how entire processes could work differently, with AI connected to the financial data and business context it needs.
For Guesty, it’s a natural progression. The same financial foundation that helped Barry reduce manual work and gain visibility across a complex business is now supporting a new generation of AI workflows, without sacrificing the control or flexibility finance requires.
And for Barry, that’s changed the way he thinks about what’s possible.
Datarails provides Barry with a holistic view of Guesty’s finances, allowing him to see not just the annual budget and actuals, but also detailed insights such as trends, amortized expenses, and approved purchase orders that haven’t yet been paid.
The game changer with AI isn’t just doing the same tasks faster. It’s being able to create entirely new workflows and change the way finance works.
