Senior Product Manager/Head of Product

Cover letter required. Applications without one will be ignored.

The Opportunity

We'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 With

You'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 Solving

This 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 day
• Building pre-swipe controls, approval hierarchies, and policy engines that are powerful enough for a CFO and simple enough for a field employee
• Commercializing fintech capabilities — corporate cards, embedded payments, LLM-powered fraud detection and policy compliance — that most competitors haven't touched yet
• Defining 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 For

• 6–10 years as a developer, designer, or PM with at minimum 2 years as a Product Manager— you've shipped real products that real people use
• Strong design fundamentals — hierarchy, usability, information architecture; you can articulate why something works, not just that it looks good
• An impeccable portfolio — work that earns a reaction before you've said a word about it
• B2B experience — you understand enterprise software, complex multi-stakeholder workflows, and the difference between a user and a buyer
• High horsepower — you work hard, you push the people around you, and you know how to celebrate when something ships
• Strategic thinker and execution machine — you can pitch vision on Monday and close tickets on Friday
• B.Sc. required (CS, Design, Engineering, or related)

Bonus: fintech experience, led platform redesigns, UX designer transitioning to PM, startup background.

Compensation & Benefits

• Above-market salary, paid in USD
• Clear 18–24 month path to Director, VP, or CPO as the company scales
• No-BS culture: you will work with incredible engineers, building a product which is affectively already sold
• Health coverage and social security registration

How to Apply

Email your resume and cover letter to [Confidential Information]

Your cover letter must include:

1. What you've shipped — links and screenshots welcome
2. Two or three software products you think are exceptionally well-designed, and specifically why — what makes them great, and what would you change
3. Something you built that you're proud of, and something you'd do differently
4. Why this role, and why now

We 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.