Head of Payment Products & Monetization

Hi! I'm Josh, Chief Product Officer at WeTravel

Multi-day travel businesses (think of a 7-day safari in the Serengeti or a 5-day scuba diving trip in the Galápagos) sell over $300B of travel annually. Ten thousand of those businesses, worth $3B in travel sales, use WeTravel as their end-to-end operating system. They use WeTravel to manage sales processes, collect payments, and run their back offices. Our powerful payment stack and AI-enabled solutions help them grow sales, save money, and save time.

WeTravel is already the leading global solution, but the opportunity ahead is an order of magnitude larger. Therefore, I'm hiring a payment and monetization product leader with payment industry expertise that far exceeds mine to help us continue to scale quickly.

The Role

Imagine you are the head of product for a vertical FinTech scaleup serving multi-day travel businesses. Your company has a strong product-market fit globally and processes $3B annually on a path to $10B in a few years.

You work weekly with the CEO and COO to drive strategy and have your name on many business outcomes. Your company has a true distribution advantage: 150 sales reps and account managers across five continents are excited to sell what you build. Vertical AI SaaS players serving the same multi-day audience co-sell with you.

If you had that job, would you be excited to go to work every day to build a global category winner?

This is the job we're hiring for, but with two differences. First, those AI SaaS players aren't external partners. They are part of the same company. So you can just build together with them. Second, you will report to me as the WeTravel CPO. Our CEO Ted and I will provide the company-wide guidance and lean on you for a dual mandate: build a $10B+ FinTech stack and scale our monetization engine around payments and payment-related upsell opportunities, which together account for over 80% of WeTravel revenue.

The Scope

You'll own the entire flow of money at WeTravel - "follow the money" - from signup and KYB/KYC through travelers paying organizers, organizers paying suppliers and themselves, and the financial OS experience layered on top.

• Signup, KYB/KYC, payment profile, and login - the trust and access layer for every business running its money on WeTravel.

• Money In: travelers Paying Organizers - collecting payments in 40+ currencies and 30+ payment methods at locally competitive rates, plus highly monetizable upsell products like travel insurance at checkout.

• Money Out: Organizers Paying Suppliers - paying the right supplier the right amount, in the right currency, on the right date, and helping organizers discover and book suppliers through WeTravel. This area includes highly monetizable opportunities like supplier virtual cards and supplier booking marketplace.

• An AI-assisted financial OS experience - currency-level wallets, full visibility into money in and out, and a back office experience like Ramp and Bill.com built specifically for multi-day travel businesses.

• The foundation - PSP and vendor orchestration, a real-time payment ledger, security and compliance certifications, and a risk management built to support $10B+ in annual volume.

Structure and Resourcing

You will report to me (CPO) and join our LT (leadership team) from Day 1. You will partner with our CEO/COO on commercial and risk/compliance decisions. You will lead product, design, engineering, and GTM teams to build and sell (Design, Engineering, and GTM report through their functions, but will follow your lead).

These five areas today have 2 PMs, 2 designers, and 15 engineers. This is a modestly sized but strong, well-balanced group including ex-founders, ex-head of design at a financial OS startup, and the most tenured engineers at WeTravel. You’ll strengthen this group and add more talent to it in 2026 Q4 through 2027 to further accelerate our revenue.

This role includes making board-level strategic decisions, managing a high-performance team, and personally PM’ing features based on need. This existing group has accomplished a lot on its own around Traveler Pay-In & Upsell, Supplier Payout “rails”, and some aspects of the Foundation. When you first start, you will uplevel their work while leading the cross-cutting areas like the AI-Assisted Financial OS Experience hands-on. In an AI-powered PM-GM era, Ted and I believe leading from the front is the most impactful and rewarding shape of a product leadership role (I still ship 2-3 features a year). It’s not about the number of reports but customer impact, business impact, and cultural impact.

An Ideal Candidate

We are looking for a lot in one person given the importance. The ideal candidate:

• Is an exceptional product leader and product manager with a GM mindset. Has a strong track record of driving business outcomes through both hands-on PM work and leadership.

• Has deep expertise across most aspects of building and scaling FinTech products and companies. Having depth in one to two areas alone-whether that’s payment processing or issuing-is not enough. This broad depth comes from having lived it for well over a decade, and forever remaining a student of it.

• Has managed both 0-to-1 and large scale, and knows how to build for each maturity stage.

• Can optimize growth, margin, risk, and compliance together, in productive collaboration with x-functional partners.

• Would strengthen our global, low-ego, ambitious culture. Has the desire to win and the capacity to produce outcomes.

Travel FinTech experience is helpful, but not required.

Benefits

• Competitive salary and equity.

• Generous "Time to Recharge" policy - enjoy unlimited paid time off to rest, recharge, and show up as your best self.

• Work remotely for a maximum of 4 weeks per calendar year.

• Extensive paid family leave.

• Three paid volunteer days per year - take time to give back to causes you care about, on us.

• Cycle-to-work scheme (Swapfiets subscription) or commuting reimbursement.

• Monday/Thursday team lunches and after-work social events.

• Cutting-edge equipment and tools to set you up for success.

• Join an international, travel-loving team with a passion for adventure and innovation.

Equal Opportunities

WeTravel is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We welcome applicants from all backgrounds, experiences, and perspectives. If you're excited about this opportunity and believe you're a good fit, we encourage you to apply and join us in transforming the travel industry!