The Public Ledger: The Rise of the Bots

Hello, Fintech Friends!

For observers of the payments and fintech industries—like myself—most of our time recently has been spent considering the risks and opportunities presented by AI. For the most part, payment and fintech companies have been on the losing end of hypothetical arguments about AI’s impact—just check out their share prices!

Among the questions that keep investors, and possibly CEOs, up at night is whether autonomous agents will fundamentally reshape commerce, whether AI native startups will overwhelm incumbent commerce platforms with better, faster, cheaper software, and whether AI-powered schemes will swamp current fraud systems, racking up significant losses for industry participants. Unfortunately, for payments and fintech companies, the burden of proof rests with them. And even though financial results continue to be generally favorable, it is exceedingly difficult to disprove a bearish AI thesis over the near-term.

After listening to last week’s On The Block session featuring Brad Axen, a key architect of Block’s AI strategy and capabilities, including its internal tools and customer-facing features, I thought it would be a good idea to provide a progress report on AI initiatives in flight across payments and fintech, focusing specifically on AI-powered assistants (i.e., bots) at leading commerce platforms.

Although Block’s decision to dramatically reduce its workforce based on AI advancements grabs the headlines, it is only part of their AI story. Moneybot, an AI-enabled assistant for Cash App users, promises a new way to interact with your money. Although the company pledged a broad release within months when the feature was introduced last November, as of last week, just 20% of Cash App users had access. Similarly, Managerbot, an AI partner for small businesses using Square’s point-of-sale system, remains in beta testing. For a company that holds itself out as an early mover and leader in AI, their pace of shipping AI features seems rather pedestrian.

On the other hand, Toast IQ, a similar AI-powered copilot for restaurants using Toast’s technology platform, has been widely released to merchants, with Toast noting that through the first four months post-launch, more than half of Toast’s 164,000 locations have used the feature.

Sidekick by Shopify—which helps online sellers build websites, design apps, create content, and manage their business—also seems further along, with Shopify noting “hundreds of thousands of merchants” using it to run core parts of their business as of early November 2025.

Finally, Intuit’s virtual team of AI agents—across payments, accounting, finance, customer service, marketing, payroll, and project management—have been used by over 3 million Intuit customers, with all time repeat usage at more than 85%.

Of course, we are in the early days of AI. While many companies race to offer AI-enabled features, most consumers and small businesses are moving slower to fully adopt. Like frontier models, AI-powered assistants should improve, perhaps dramatically, as companies iterate and feed them with more proprietary data. So, no need to worry, there’s time to catch up…or fall behind. May the best bot win!

Disclosure: As of April 8, 2026, I have long positions in Block and Intuit.

Bob Hammel

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