According to The Verge, in a recent Decoder podcast interview, Square’s global head of product Willem Avé detailed the “seismic shift” of AI for small businesses and Block’s company-wide functional reorganization from last year. He explained that this new structure creates a single, shared roadmap across units like Square, Cash App, and even Tidal, sharing engineering resources to push into financial automation. Avé argued the key to useful AI is linking nondeterministic large language models to deterministic financial systems to move beyond gimmicky chatbots. He also confirmed Square moves at least 16.7 million pennies between merchants and customers weekly, a practice facing change with the coin’s discontinuation, and reiterated Square’s commitment to enabling Bitcoin payments for merchants despite low transactional use.
The functional reorg and why it matters
Okay, so Block—Square’s parent company—restructured into a functional organization last year. That’s a huge deal, and it’s the kind of inside-baseball move that most people would gloss over. But here’s the thing: it means the team building payment rails for Square might also be working on infrastructure for Afterpay or, weirdly, the music streaming service Tidal. Avé’s argument is that this creates alignment and a shared tech roadmap. I’m skeptical. Sharing resources across totally different industries (payments vs. music?) sounds like a recipe for bloat and slow decision-making. He admits Square might not move as fast as an independent division, but claims the benefits in cohesive product development are worth it. This is a big bet that the core financial tech underneath all these services is more similar than different. If it works, it could be a powerful moat. If it doesn’t, it’s corporate overhead disguised as synergy.
AI’s real shift for small business
Avé cut through the AI hype with a surprisingly technical and useful framing. The goal isn’t just to slap a chatbot on a dashboard. It’s to take the “nondeterministic” (read: unpredictable, creative) outputs of an LLM and chain them to “deterministic” (reliable, rule-based) financial systems. Think about a florist asking, “What should I stock for Mother’s Day based on last year’s sales and this year’s weather forecast?” The AI can brainstorm, but the final action—ordering 50 more pink roses—must trigger a precise inventory and purchasing workflow without hallucinations. This is the hard, unsexy work that turns AI from a toy into a tool. For companies deeply embedded in business operations, like Square, this integration is the real product. It’s less about generating marketing copy and more about automating complex, data-driven decisions. That’s where the real productivity gains for a small business owner will come from.
bitcoin-pennies-and-the-weirdness-of-money”>Bitcoin, pennies, and the weirdness of money
This is where the conversation got fascinating. We’re in a bizarre monetary moment. The U.S. is discontinuing the penny—and Square is processing 16.7 million of them weekly—while also holding large Bitcoin reserves and enabling crypto payments. Avé made the philosophical case for offering Bitcoin as a payment choice, even though he basically acknowledged nobody uses it to buy coffee. It’s not about today’s utility; it’s about building the infrastructure for a potential future. Meanwhile, the humble penny’s demise is a more immediate, practical headache for the cash-based businesses Square serves. It highlights the company’s position straddling two worlds: the gritty reality of daily cash transactions and the speculative frontier of digital assets. They have to navigate the end of physical currency while betting on a decentralized digital one that’s still mostly used for speculation. Talk about a balancing act.
The ecosystem and the road ahead
The discussion about the headphone jack was nostalgic, but it points to Square’s core thesis: reduce friction for the seller at all costs. From the open headphone jack, to Bluetooth, to tap-to-pay on a merchant’s own phone, the goal is instant, easy onboarding. Avé was diplomatically quiet about potential platform constraints from Apple or Google, which is telling. Square’s future—its “Square 3.0″—depends on deeply integrating with these mobile ecosystems while also building its own dedicated hardware for larger clients. The fusion of Square and Cash App ecosystems under Block is another huge part of that roadmap. So, what’s next? More automation, smarter insights, and a platform that tries to be everything for a business, from accepting a Bitcoin payment (via the Lightning Network, perhaps) to predicting next week’s best-selling item. The risk is becoming a jack-of-all-trades. The opportunity is becoming indispensable.
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