Head of Design

Meet BOB BOB is a free finance employee for businesses. Bob does the books, pays vendors, chases invoices, and answers any money question you throw at him. He works through regulated financial partners, with the controls and approvals needed to move real money safely. Our whole philosophy is that Bob is real. When work comes up, we ask one question: why not just give it to Bob? We believe AI agents are becoming economic actors. Done right, that gives every founder and business more leverage—not less control. We’re building the financial infrastructure that makes that future useful, safe, and available to anyone with a business to build. We’re backed by Circle Ventures and founders of PayPal, Zynga, and Plaid—including Peter Thiel, Mark Pincus, and Zach Perret. The role You’re our first design leader. You report directly to the founder and own how Bob looks, feels, and works. This is a hands-on role. We’re not looking for someone to manage an agency or make decks about design. You’ll talk to users, work through the product, make the prototypes, and ship alongside engineering. The hard part is making something genuinely new feel obvious. Bob has to handle complex financial work without feeling like accounting software. He has to be powerful without being intimidating, autonomous without feeling out of control, and trustworthy without becoming boring. You’ll own: The product experience from onboarding through daily use. How people give work to Bob, understand what he’s doing, and step in when needed. High-trust workflows around approvals, payments, account state, exceptions, and financial controls. The interaction model for an AI finance employee—not another chatbot bolted onto a dashboard. The design system and product-quality bar across web, mobile, and conversational surfaces. Prototypes that help us answer hard product questions before we write a lot of code. Research with real users. Watch them work, find the friction, and fix it. The visual expression of Bob inside the product, in close partnership with Growth Marketing. The design team—when the product and workload justify building one. Who you are We hire for three things: You really care. You care about the mission, the user, and every detail of the experience. It shows. You have taste. You know amazing work from good enough, and you can’t ship good enough. High agency. You don’t wait for the perfect brief. You find the real problem, make the work, and get it shipped. You’re a world-class hands-on product designer. Your portfolio shows simple, coherent products built over genuinely complex systems. You think in systems without losing the human moment. You can design the happy path, the failure state, the weird edge case, and the explanation that makes all of it understandable. You have strong opinions, but you aren’t precious. You can take feedback, defend the work, change your mind, and keep moving. You’re excited by AI, but you don’t confuse a chat box with a product. You think carefully about agency, trust, memory, interruptions, approvals, and how humans stay in control. Fintech, payments, accounting, developer tools, or other high-trust product experience is a big plus. Strong prototyping and frontend instincts are even better. The office In person at our Miami office on the Venetian Islands. Small team, high trust, zero bureaucracy. It’s a fun place to work. Comp Competitive salary + equity. Early hire, real ownership. #J-18808-Ljbffr