Staff Product Manager

What do we do? Paddle offers digital product companies a completely different approach to their payment infrastructure. Instead of assembling and maintaining a complex stack of payments-related apps and services, we’re a Merchant of Record for our customers. That means we take away 100% of the pain of payment fragmentation. It’s faster, safer, cheaper, and, above all, way better. We’re backed by investors including KKR, FTV Capital, Kindred, Notion, and 83North and serve over 6000 software sellers in 245 territories globally. The Role: We are looking for an exceptional Staff Product Manager to lead our flagship Checkout experience – the most strategically critical, highest-visibility product surface at Paddle. Every dollar our customers earn flows through Checkout. This is a massive-scale engine: we handle ~10 million sessions a month, processing $180M+ in monthly payments across a global network of 10,000+ sellers. The decisions made here directly move the needle on conversion, revenue, and customer trust. This is the toughest product role at Paddle, and we're looking for someone who is energised by that. You will own the Checkout product end-to-end: its strategy, its roadmap, its performance, and its commercial outcomes. You'll operate as the senior product voice in the room with our executive team, engineering leaders, and largest customers, and you'll be expected to set the bar – not just for what we ship, but for how the wider product org makes decisions, runs discovery, and uses data. You'll work in a trio with a strong engineering lead and an experienced product designer, with daily exposure to Sales, Solutions, Customer Success, Risk, Finance, and Exco. Given the cross-functional intensity of the work, this role requires regular in-person collaboration with the Checkout team and the wider Payments group. This is an opportunity for a staff-level operator who wants to own a product that genuinely matters – one with hard technical problems, real commercial stakes, and the platform to influence company strategy. What you'll do: Strategy & Roadmap Ownership: - Own the long-term vision and strategy for Checkout, grounded in market trends, payments innovation, customer needs, and Paddle's commercial goals. Translate this into a roadmap you can defend at Exco and to customers. - Make – and stand behind – the tough prioritisation calls. Navigate ambiguous, multi-stakeholder trade-offs where the "right" answer requires deep judgement across technical constraints, commercial impact, compliance, and UX. - Set the bar for discovery and prioritisation across the wider Payments group; coach other PMs on how to do this well. Product Development & Delivery: - Lead end-to-end delivery of complex, multi-faceted initiatives without needing oversight. Define and enforce the delivery standards (discovery, specs, experimentation, launch quality) that the rest of the product team operates against. - Work in a tight trio with engineering and design to ship fast, instrument well, and iterate based on real customer signal. Use AI tooling to compress the loop from idea to spec to prototype – we expect ideas to be testable in days, not weeks. - Run a continuous programme of optimisation – A/B tests, beta programmes, usability research – to compound conversion and UX gains across a high-volume, consumer-facing surface. Data, Metrics & Commercial Impact: - Own the KPIs that matter for Checkout (conversion, authorisation rates, revenue impact, NPS, etc.) and weave them into the strategic narrative for the business. - Dive into data independently. We don't expect you to wait for an analyst; we expect you to pull the numbers (with AI help where it accelerates you), form a hypothesis, and bring a recommendation. - Use product data to influence business strategy beyond your immediate roadmap – pricing, GTM, risk policy, settlement, etc. Stakeholder Management & Storytelling: - Align senior stakeholders – including Exco, Sales leadership, and key customer