Lead Product Manager - Checkout & Monetization

Hi! 👋 I'm Josh https://www.linkedin.com/in/wjoshchang/, Chief Product Officer at WeTravel 🇳🇱 I'm hiring a Lead Product Manager to own our checkout and the monetization built around it. You will report to our incoming Head of Payment Products & Monetization. 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 around the world. 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. WeTravel is their eCommerce stack, with checkout at the center of it. WeTravel has 400+ team members representing more than 88 countries. Our Amsterdam office in Rokin is home to the entire Product Org and most of our Engineering team. Financially we are secure and growing fast, with 60 to 100 percent year-over-year growth depending on the metric. [https://app.ashbyhq.com/api/images/user-content/a282d470-f784-41cc-a7ec-98a3218eb13c/5d303d17-c3bb-4553-b5a1-148feccd7c21/image%20(4).png] THE ROLE This is an impactful and intellectually rewarding (senior IC) role across many dimensions. Impact Our ten thousand clients (travel businesses) use our checkout to complete $3B of travel sales. Their business outcome is dependent on our checkout. For WeTravel, 80% of our revenue comes during checkout. We monetize checkout through a booking fee, an FX markup, and payment method margin. Because the traveler pays the organizer via WeTravel, we can upsell additional products to travelers during checkout. Travel insurance has been a hit as an upsell, and there are other opportunities you can explore (airport transfers, eSIM, visa application service, etc.). A separate Payments PM owns payment rails, currency coverage, and processing. You own the traveler experience, conversion, margin optimizations, and ultimately the revenue. Intellectual complexity First, one checkout has to serve ten thousand clients who sell travel in different ways. Some sell thousands of standard packages a year, while others sell tens of very expensive trips. Some want personal configuration at checkout, others want it stripped down. Some trips run multiple times every month, some run once. Most are expensive enough to need installment plans. Some care about cross-domain conversion tracking while others care more about the luxury look and feel given their elevated price points. All of this has to work well across 40+ currencies, 30+ payment methods, and four transaction types—full trips, payment links, in-person QR payments, and business payments. Finally, checkout needs to be a modular “system” that other teams can easily build into. Second, FX markup and traveler upsell are win-win monetization that we've only taken 0→1. They already save clients time and cost on currency conversion and pay them revenue share on insurance upsells. Growing them requires thinking through value for clients, value for their customers (travelers), value for WeTravel, vendor landscape, appropriate UX, fund flows, and everything else. This requires a GM-like ownership mindset, strategic and analytical thinking, and ability to operate cross-functionally. GOALS FOR THE FIRST YEAR These are the ideal goals based on what we know today. We’ll learn as we go and calibrate together. Checkout - Revamp checkout into a flexible and cohesive system. - Make the new checkout presents what our clients sell in the best way possible to maximize their sales on both mobile and desktop, and for all the variations of what they sell and how. - Build a systematic way to track and optimize conversion, margin, and other factors all together. Enable clients to track performance across their demand channels through our checkout. - Ensure it’s easy for other teams to implement their features within the checkout experience, and own the standard they build against. Inversely, checkout should be able to evolve without unnecessarily requiring changes on the rest of WeTravel systems. Monetization - Increase checkout FX revenue by 30-50% by optimizing adoption and markup. This includes improving the UX and pricing (which can be lower or higher depending on currency pairs), while relying on the Payments PM for currency coverage. - Increase insurance revenue by 30-50% by offering more choices, covering more geographies, improving adoption, and using multiple vendors. - Pilot two other traveler upsell products and start to scale them. AN IDEAL CANDIDATE Requirements: - Deep product management experience owning real outcomes, not just execution, over many years and having learned from the battle scars. - 10+ years in product management is ideal (staff level) - 7+ years is minimum (senior level) - Broad ownership of all things checkout across multiple phases of its evolution. Optimizing one part of the checkout is not enough. - System thinking to create a flexible and cohesive checkout system that other teams can easily build into. Ideally, you’ve built a multi-purpose checkout system before and know the best practices and pitfalls. - Combination of analytical thinking and UX insights to optimize that checkout system, including the judgment to know when a test will tell you something and when it will not. - Expertise in conversion across funnels on both mobile and desktop. - Track record of improving monetization, especially as cross-sell/upsell. The strongest version of this is having taken an upsell from 0 to 1 and scaled it into one of the largest revenue sources at your company. Nice to haves: - Experience with pricing on a live transactional surface, where a price change and a UX change can move the same number in opposite directions. - Experience building whitelabel eCommerce solutions like Shopify. - Experience optimizing x-domain conversion from advertising surfaces to checkout. - Experience with travel insurance, pre-booked ground transportation, or travel activities. - Experience with multi-currency and cross-cultural checkout, where conversion behaviour differs sharply by market. 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!