AI Gives Main Street the Power to Play Like the Fortune 500

The great divide in American business has traditionally been defined by scale. The Fortune 500 enjoyed the advantages of large finance teams, sophisticated systems, and the operational resilience that comes from institutional infrastructure.

Small and medium-sized businesses (SMBs) were left to fend mostly for themselves, however they could, with whatever semi-diluted enterprise-grade tools they could afford to integrate.

But the intersection  of AI, automation, and a fundamental shift in software design suggests that the balance of power is shifting. And René Lacerte, CEO and founder of BILL, said it could be tilting in the favor of the millions of Main Street SMBs supporting the U.S. economy.

“The unlock is going to be tremendous. AI is going to enable people to explore dreams and passions they never thought of before. … I think it’s a huge, huge equalizer,”  Lacerte told PYMNTS CEO Karen Webster during a recent conversation.

“We’ll [soon] be talking about the Fortune 500 wanting the agility of the Fortune 5 million,” Lacerte predicted, noting that if the last 20 years were about giving SMBs the tools of the enterprise, the next 10 may invert the equation.

From Automation to Autonomy

For its own part, BILL processes payments totaling about 1% of U.S. GDP and serves close to half a million businesses through an 8 million-strong two-sided network. That history has been about automation. But the next chapter, Lacerte argued, is about autonomy.

When Webster asked what it means for “every small and medium-sized business … the little corner café, the graphic design firm, the contractor” to have the same financial firepower as a Fortune 500 company, she stressed the structural question: What happens when the office of the CFO goes autonomous for the “Fortune 5 million”?

“Actions taken care of themselves … data entry, invoice collection, payments automatically being scheduled,” Lacerte said.

“In a Fortune 500 firm, all the accounting happens by a team of people,” he added. “In SMB, you wear all the hats. You are a Jack or a Jill of all trades.”

BILL’s go-forward thesis is that AI agents can absorb enough of the financial back office that small businesses can redirect scarce energy toward creativity, strategy and growth.

Still, Webster raised the practical question that haunts every technology wave: “Can the benefits of AI overcome organizational inertia?”

Lacerte believes they can when the technology eliminates problems, not just improves them. The more AI can “take all that rote work and make it automated,” he said, the more it chips away at not only the inertia of switching systems, but the inertia of starting a business at all, and the fear of back-office complexity that keeps many would-be entrepreneurs on the sidelines.

“You don’t have to worry about how the back-office works,” Lacerte said

He pointed to Bill’s W-9 agent as an example. Collecting W-9s from suppliers to file 1099s is a classic back-office headache, often landing in the busiest time of year for both buyers and vendors. Now, every time a new supplier joins the platform, an agent automatically collects the W-9 in advance.

BILL estimates that this could save about 80,000 days of work across its platform.

Competition, Differentiation, and the AI Moat

Websters also asked whether AI was changing the competitive landscape for providers serving SMB CFO functions. Bill set out to define the category 20 years ago. Now, the field is becoming crowded.

“The competition is more today than it was … but we think our leadership position allows us to continue to lead and redefine the category,” Lacerte said, citing a combination of workflow expertise, payments capability, distribution via accountants and partners like NetSuite and top banks, as well as a scaled network as the real moat.

AI, he stressed, is an amplifier of those assets, not a substitute for them. AI agents can sit atop BILL’s foundation, enabling systems that not only detect patterns but predict what should happen next.

“Our ability to uniquely identify what an SMB does and needs to do from a workflow perspective is something that we do well. Moving money is something we do exceptionally well,” Lacerte said. “All of those things play into how you leverage AI.”

The inflection point did not arrive overnight. Lacerte characterized it as a culmination of decades of industry groundwork: digitization, cloud adoption, document capture, and the emergence of BILL’s “two-sided network” of millions of interconnected businesses.

The Human Edge in an Autonomous World

Looking back across two decades, Lacerte identified one change more consequential than any technological advancement: the death of the desk. Early customers faxed documents and feared cloud storage. Today, the phone can be the office.

The transition from paper to cloud was not merely modernization but a guardrail against operational fragility, as illustrated by a jeweler who adopted BILL after water damage destroyed her basement of paper invoices. AI, Lacerte suggested, is simply the next layer of that resilience.

Asked by Webster for one human skill every business owner should cultivate in the age of AI, he doesn’t hesitate: “Empathy. … Empathy for understanding employees, understanding SMBs, especially in this era of AI.”

In his view, empathy is the connective tissue between leaders, teams and customers, an attribute that cannot be replicated by models or agents. It shapes judgment, guides communication, and anchors trust. In a world where operations are increasingly automated, empathy may become the defining competitive advantage.

“For us, the mission from day one has been to make it simple to connect and do business. … Empathy is a connection point, and it also allows us to learn. Business owners leaning into empathy is something that AI can’t replace. It will lead to the unlock of what we as humans can provide for society,” Lacerte said.