Head of GTM

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 $160K–$210K base + equity. Early hire, real ownership.

The AI-powered OS for beauty, wellness and self-care About Fresha Fresha is the AI-powered operating system for the global beauty, wellness and self-care industry, connecting and powering everything from salons and barbers to spas, medspas, fitness studios and health practices. Trusted by millions of consumers and businesses worldwide. Fresha is used by 140,000+ businesses and 450,000+ stylists and professionals worldwide, processing over 1 billion appointments to date. The company is headquartered in London, United Kingdom, with 15 global offices located across North America, EMEA and APAC. Fresha allows consumers to discover, book and pay for beauty and wellness appointments with local businesses via its marketplace, while beauty and wellness businesses and professionals use an all-in-one platform to manage their entire operations with an intuitive business software and financial technology solutions.   Fresha’s ecosystem gives merchants everything they need to run their business seamlessly by facilitating appointment bookings, point-of-sale, customer records management, marketing automation, loyalty, beauty products inventory and team management.   The consumer marketplace unlocks revenue potential for partner businesses by leveraging the power of online bookings and automated marketing through mobile apps and advanced integrations with major tech brands including Instagram, Facebook and Google. Role Overview   Given our exciting and progressive growth plans,  we are looking for an exceptional Account Manager to come and join our global business.   Reporting directly into the Head of Account Management, and working collaboratively with commercial, marketing & product teams, you will be accountable for building long-term relationships and driving revenue growth and retention of the Fresha platform.    This is a great opportunity for someone looking to work in a fast-paced and changing environment, who likes to work autonomously, enjoys a challenge and wants to make an impact.   To foster a collaborative environment that thrives on face-to-face interactions and teamwork, all Fresha employees work from the office five days per week.