The following is a guest post from Michel Rbeiz, senior vice president and general manager of fintech at Toast. Opinions are the author’s own.
When a restaurant fails, many people assume the food was bad or the service was slow. The reality is often quieter and more complicated: many operators struggle to navigate their finances — not because they aren't capable, but because their tools aren't built for how restaurants actually work.
Most businesses can weather a late payment or a broken piece of equipment, but the restaurant model is uniquely unforgiving. The average restaurant operates on pre-tax margins of 3%-5%, which leaves little buffer for anything to go wrong. And things can go wrong fast: Friday's dinner rush sits in settlement limbo while Monday's payroll comes due, and somewhere in between, the walk-in compressor dies. This isn't a management failure. It's a planning and resiliency problem.
Almost every operator has asked themself, "Will my revenue cover my outflows over the next 30 days?", "Can I weather this?", “What are my options?” — usually in the middle of the night after the compressor dies. They’re missing financial tools built around how restaurants actually make and spend money, and that troubleshoot when those two things fall out of sync — like agentic AI tools that proactively manage cash flow and keep the books current in the background.
Why financial tools fail operators
The industry has told itself a story that operators are drowning in "too many tools." The deeper problem is that the tools don't talk to each other, and every seam between them costs the operator something — time, money or sleep. I call this the complexity tax, and it shows up at three levels:
Predictability. An operator who can't see their real cash position in real time can't plan. Toast's 2025 Voice of the Restaurant Industry Survey found that improving profitability is the top priority for 40% of operators, but they’re forced to steer by looking in the rear-view mirror. Financial reports arrive on the 20th of the following month and take hours to assemble. That’s too late to influence decisions made in the weeks before.
Durability. Even when operators can see what's happening, they often can't act on it fast enough. The timing mismatch between inflows and outflows is the fragility, all of which compounds into a slower, more stressed business.
Profitability & Growth. Without predictability and durability, operators can't invest in the work that compounds margin: menu expansion, local marketing and new location planning. They're stuck playing defense on cash instead of offense on growth. The complexity tax does more than cost hours. It caps ambition.
Cutting through the complexity: what operators should look for
Operators need financial tools that run in the background so they can run the restaurant. Here’s how to find and get the most benefit from them.
Ask the right questions
Whether a given tool will work for an operator often depends on how much work the tool requires of them.
Robbie Soskin, co-owner of yum! kitchen and bakery in Minnesota, starts every analysis of a new financial tool with the same question: “What needs to be true for this to work? For example, do I need to move money to a different account for the tool to know what my outflows are or will it connect with my existing accounts, bill pay or accounting software?”
This question determines what a tool demands versus what it promises, and gives an operator a concrete understanding of how it will reduce the complexity tax.
Another important question about capital and financing tools, especially for a new restaurant: do they offer a flexible payment structure for operators? The complexity tax is highest in a restaurant’s early days, with significant upfront costs to get the business up and running paired with zero revenue certainty.
These tools should offer payment structures that scale with daily transaction volumes rather than requiring fixed monthly commitments. This aligns an operator’s financial obligation with the stabilization timeline for their new business.
Find agentic AI tools that earn your trust
Ideally, agentic AI tools that sit across cash flow, accounting and capital build proactive financial management into a restaurant’s operating system: surfacing issues before they become emergencies, suggesting solutions tailored to how the restaurant operates, and acting on them.
But handing over the keys to an AI agent is an understandably big step for many operators, especially when it comes to managing money. “Trust will be a big barrier for agentic AI adoption” in the restaurant industry, Robbie says. Operators should look for tools that take concrete steps to earn their trust.
In practice, this can look like tools that analyze their own success. Consider an AI agent that projects a cash shortfall two weeks out based on your current sales pace and upcoming invoices, then recommends options like adjusting payment timing or flagging a capital draw. After two weeks, the tool can report back: Was its projection accurate? What are the implications for the next week’s cash flow?
Operators can also seek out agentic AI tools that understand and respond to their specific context and ever-changing variables. If taxes are due on the 15th of a given month while a water bill is due on the 14th and a payroll cycle hits every other Friday, the agent should map those deadlines against projected revenue and move money accordingly. This can be the difference between an operator who catches a problem before it compounds and one who learns about it on the 20th of the following month.
Reframing success
Restaurants have accumulated large integration debt over the last decade, and it shows up every time an operator has to log into five systems to answer one question. The operators whose financial tools close that gap for them first will pull ahead.
The measure of progress is an operator who knows where their cash flow stands when their compressor dies unexpectedly
