Cover letter required. Applications without one will be ignored.The OpportunityWe're on a mission to 10x a profitable, 25-year-old SaaS platform — and we need one exceptional person to lead the charge.ExpensePoint serves 850+ enterprise customers across North America, processes millions of dollars in expense transactions, and has real revenue with a loyal customer base that's been with us for years. The foundation is solid. What we need now is someone to tear up the UX playbook and rebuild it for the modern era — AI-native, card-first, and fast.The customers are already there. The revenue is already there. What's missing is you.Who You'll Work WithYou'll report directly to and work daily with our CEO — a former Senior PM at Google with an HBS MBA and McKinsey background, who thinks in systems, moves fast, and has zero patience for bureaucracy. You'll also work closely with a tight-knit engineering team that ships, argues about the right solution (in a good way), and genuinely cares about craft.This is not a company where product ideas die in Jira. Decisions get made in days, not quarters. If you bring a compelling case, you'll see it in production within weeks.The Problems You'll Be SolvingThis is a genuinely hard product challenge. You're not adding a feature to a mature platform — you're reimagining how thousands of employees at mid-market and enterprise companies think about spending money at work. That means:Redesigning a complex, workflow-heavy platform without breaking what 850+ paying customers depend on every dayBuilding pre-swipe controls, approval hierarchies, and policy engines that are powerful enough for a CFO and simple enough for a field employeeCommercializing fintech capabilities — corporate cards, embedded payments, LLM-powered fraud detection and policy compliance — that most competitors haven't touched yetDefining what "great" looks like in a category that has historically settled for "functional"The gap between what enterprise expense software looks like today and what it should look like is enormous. That gap is your canvas.What We're Looking For6–10 years as a developer, designer, or PM with at minimum 2 years as a Product Manager— you've shipped real products that real people useStrong design fundamentals — hierarchy, usability, information architecture; you can articulate why something works, not just that it looks goodAn impeccable portfolio — work that earns a reaction before you've said a word about itB2B experience — you understand enterprise software, complex multi-stakeholder workflows, and the difference between a user and a buyerHigh horsepower — you work hard, you push the people around you, and you know how to celebrate when something shipsStrategic thinker and execution machine — you can pitch vision on Monday and close tickets on FridayB.Sc. required (CS, Design, Engineering, or related)Bonus: fintech experience, led platform redesigns, UX designer transitioning to PM, startup background.Compensation & BenefitsAbove-market salary, paid in USDClear 18–24 month path to Director, VP, or CPO as the company scalesNo-BS culture: you will work with incredible engineers, building a product which is affectively already soldHealth coverage and social security registration How to ApplyEmail your resume and cover letter to jobs@expensepoint.comYour cover letter must include:What you've shipped — links and screenshots welcomeTwo or three software products you think are exceptionally well-designed, and specifically why — what makes them great, and what would you change?Something you built that you're proud of, and something you'd do differentlyWhy this role, and why nowWe read every cover letter. Generic ones get closed immediately. Show us how you think.ExpensePoint is building the future of spend management for North American enterprises. If you want to own something real — a product that will touch thousands of companies and the people who run them — we want to hear from you.Equal opportunity employer. We hire for talent, passion, and execution — nothing else matters.