Why small businesses hesitate on AI in finance, and how BILL is addressing it

Why small businesses hesitate on AI in finance, and how BILL is addressing it by Tearsheet

Allen Bonde, Chief Marketing Officer at TreviPay, argues that a new generation of digital-native buyers is the biggest force reshaping how businesses buy and pay. Accustomed to frictionless consumer experiences, they expect the same convenience and omnichannel consistency from their suppliers. They are also more open to alternatives like stablecoins, net terms modeled on consumer BNPL, and AI as a co-creator. Sellers, meanwhile, are working to retain and keep their best customers happy in a tight macro environment, where the cost of capital puts pressure on businesses to extend credit and get paid faster.

Most AI startups chase breadth. They build a capable, general-purpose product and sell it across as many industries as are willing to buy it. Ari Malik, CEO of Salient, took the opposite approach. He picked one vertical, auto lending, and went deep enough that he eventually moved his company's headquarters to Los Angeles to be closer to a single customer, Westlake Financial. Two years later, Salient is live inside roughly half of the top 20 auto lenders in the country. By Malik's account, the company has never lost one. In today’s episode, he walks us through how a decision that "wasn't really ideological" turned into a full-stack servicing layer now handling collections, total loss, compliance, and loss recovery for some of the largest lenders in the U.S. The origin story is less a strategic plan than lived experience. Malik came to the problem through the finance side of a prior company, Tesla, where he got a close look at how tangled loan servicing had become. “The workflows in this hyper-regulated part of the economy were so tangled with compliance obligations, state-specific regulations, legacy systems that weren't API-friendly or real-time,” he said, “that we sort of felt like you could build something generic and horizontal, and actually have it work.” Malik’s conviction has only hardened as horizontal AI tools have tried to move into consumer lending and run headlong into compliance violations. For Malik, the read was simple: a market this large and this regulated was ripe for going deep.

Nubank spent thirteen years building one of the most loved financial brands in Latin America, growing past 140 million customers across Brazil, Mexico, and Colombia. This month, that brand entered the US for the first time, launching Nu Global alongside a dedicated US product built around a Nu Account and a no-annual-fee credit card. Ethan Eismann is the executive tasked with making that experience work. As Nubank's first Chief Design Officer, reporting directly to founder and CEO David Vélez, Eismann oversees design strategy across the company's entire product ecosystem. He joined Nubank in mid-2025 after two decades leading design at Google, Adobe, Uber, Airbnb, and Slack.

For the second episode of The Editors’ Room, we flipped the format around. One trend we think the industry is overhyping, and one that isn’t getting nearly enough attention. Managing Editor Sara took the overhyped side: the race to become a customer’s primary financial relationship. Founding Editor Zack’s underhyped pick was something that gets little attention in the larger scheme of things: the continued importance of bank branches.

When Silicon Valley Bank collapsed in March 2023, it took with it a bank that had quietly become infrastructure for the startup ecosystem, holding the majority of the venture debt market and serving as the one relationship founders and fund managers trusted for everything from a wire transfer to an introduction. Bigger banks and a wave of neobanks moved fast to fill the void. Three years later, the question is whether either one actually replaced what SVB was. Today I'm joined by Katya Kohen, managing director at Stifel, where she leads investor coverage nationally for the firm's venture and fund banking group. Katya's path into banking runs through venture, not around it. She built and exited a tech company, invested as an angel in immigrant founders, built her own accelerator, and spent years at Techstars before joining Stifel as, in her words, its first non-traditional banker. That mix of operator, investor, and now banker shapes what she calls venture banking 3.0, a founder-first model built after the SVB meltdown. We get into what actually broke in the founder-bank relationship, how Stifel has grown its venture banking book toward $12 billion in commitments, and why venture debt has become essential capital for AI companies given how capital intensive the category has become. Let's get into it.

Most banks seem to chase small business customers as one segment among many. Live Oak Bank was built around a bet that specializing beats generalizing — and it started about as narrow as a bank can start, lending only to veterinarians. Today, Live Oak has grown that thesis into 40 verticals, holds the top spot among all SBA 7(a) lenders by dollar volume, and has done it all without a single branch. My guest is BJ Losch, president of Live Oak Bank. Live Oak has never had a physical location, yet its people travel the country to sit across the table from customers a branch down the street never would. Now the bank is layering AI onto that model, cutting loan approval-to-close timelines from over 100 days toward a two-week target, and thinking hard about what it means to stay high-touch while going high-tec. We talk about the theory of verticality, where automation should and shouldn't touch the credit decision, and why BJ sees AI as an accelerant of Live Oak's strategy rather than the strategy itself.

Amy Avery, Managing Director, Analytics, Modeling and Insights, took her job at Bank of America because of a number. When she interviewed at Bank of America, she was told that the bank interfaced with, at the time, 67 million clients. "Gosh, that's so much information," she remembers thinking. "Think about what you could do with that.” She started in January 2020. Two months later, the pandemic made that abstraction very literal: the bank suddenly needed to know, in real time, how its customers were doing, thinking, and coping. Avery's job was to figure out how to answer that. Michelle Boston, Head of Data Management Technology & Enterprise Architecture, arrived by a different route entirely. She built her career in enterprise technology, rose to CIO of a startup that was eventually built and sold, and came to Bank of America first as a contractor to lead an information architecture practice. “Data has always kind of been in my blood,” she said. At Bank of America, she works at a scale few other organizations have and builds the platforms that serve as the enabling force for Avery's work. Despite a very different set of starting points, the two describe a partnership that has essentially erased the line between their jobs. "We probably know each other's jobs better now than before generative AI showed up”, Avery said, because the pace of the last two years has forced her strategy team and Boston's engineering team to make decisions in near lockstep. Listen to the full episode to hear how Avery and Boston have built a shared language across the two functions, and how they're stress-testing it against a technology cycle that seems to wait for no one.

Welcome to The Editors’ Room, a new Tearsheet Podcast series where Editor-in-Chief Zack Miller and Managing Editor Sara Khairi take the conversations that usually happen behind the scenes about our biggest stories and put them on the record. There isn’t a rehearsed interview or carefully choreographed panel answers. It’s just two editors comparing notes, challenging each other’s takes and trying to make sense of what is actually happening in financial services. Think of it as pulling up a chair after the meeting ends. It's the stuff we usually debate after the calls end: what a new product actually means, which industry trends have legs, and where the hype gets ahead of reality. Raw, conversational, and occasionally accompanied by a blooper. For our inaugural conversation, the topic was AI and, more specifically, what would you happily delegate to AI and what would you never hand over? From there, we got into the bigger question of how enterprise AI is taking shape. On that first question, Zack’s line is creativity. AI can handle planning and logistics, and he uses it as a kind of editorial sparring partner, asking questions, challenging ideas, and pushing him to dig deeper. But the creative judgment stays human. Sara draws the line at decision-making. Take an expensive laptop: she'll happily let AI compare the options, but she wants to be the person who clicks buy. It turns out that tiny distinction – AI can help make the decision, but shouldn't necessarily make it – is becoming a much bigger question in financial services.

Every account payable and account receivable department runs on the same friction: invoices chased four or five times, payments late more than 30% of the time, and credit control teams that can run 20, 30, even 50 people deep at a mid-sized corporate. Virtual cards were built to solve exactly that problem, and the growth numbers show it — spend is projected to hit $17.4 trillion by 2029, according to Juniper Research. Today I'm joined by Marc Pettican, global head of corporate solutions at Mastercard, who's spent decades working both sides of the payments ecosystem, from the merchant acquiring side to leading commercial cards. We get into what's really driving virtual card growth beyond the macro tailwinds, how MasterCard balances network economics between buyers and suppliers, and the build-versus-partner calculus behind expanding from travel into verticals like fleet and logistics, healthcare, insurance, and marketplaces. We also dig into embedded finance and the challenge of staying visible in the stack even as payments become invisible to the end user — plus where Mastercard sees its right to win in agentic payments, account-to-account transfers, and stablecoins. Marc closes with his advice for commercial card heads at mid-sized banks over the next twelve months.