Lead Product Manager

Location: While this position is posted in a specific location, all of Oyster's positions are fully remote, you can work from home, forever. To create the best experience for our new hire, this role requires you to be based within +3 / -5 UTC. We’re hiring a Lead Product Manager to own the vision, strategy, and outcomes for a critical area of Oyster’s Employer of Record product. You will shape customer-facing experiences, internal tools, and operational workflows that help companies employ talent globally with confidence, compliance, and simplicity. You will work across the full EOR system, not only individual features, to understand how customer needs, country requirements, policies, data, operational processes, and technology interact. You will start with the customer problem and desired business outcome, use direct discovery and first-principles reasoning to identify root causes, and decide whether the best intervention belongs in product, process, policy, Operations, or a combination. You’ll operate independently, making and communicating difficult trade-offs amid ambiguity. You will constructively challenge requested solutions, align senior stakeholders, and connect product decisions to measurable customer, operational, and commercial impact. You will also identify where AI and automation create real value, and where risk or customer needs call for a human in the loop. - Own the product vision, strategy, prioritization, and measurable outcomes for an EOR sub-domain. - Build a systems-level view of customer journeys, internal workflows, policy constraints, data flows, and exceptions across the EOR lifecycle. - Lead direct customer and operational discovery. Separate symptoms and feature requests from underlying problems, and evaluate product, process, policy, and operational interventions before choosing a solution. - Translate strategy into outcome-based roadmaps with clear decisions, learning plans, and success measures. - Work deeply with Operations and AI Engineers to improve scalability, exception handling, service quality, and cost-to-serve, not simply digitize existing processes. - Partner with Engineering and Design from discovery through delivery, using prototypes and technical insight to reduce risk early. - Constructively challenge and align senior stakeholders across Legal, Compliance, Finance, Operations, and Go-to-Market, and communicate strategy, trade-offs, and impact clearly in senior forums. - Contribute repeatable product practices t

✨ ONE PLATFORM, A WHOLE WORLD OF OPPORTUNITY The best jobs have always clustered in a handful of the world's wealthiest cities. But talent is everywhere. Oyster set out to close that gap - building a global employment platform that lets companies hire, pay, and care for brilliant people anywhere. We're proof that a high-performing culture doesn't need an office. Distributed across 60+ countries since 2020, we've built something the industry keeps noticing: - Ranked #10 of 250 on TIME and Statista's 2026 list of America's Top WorkTech Companies https://www.oysterhr.com/library/oyster-hr-named-10-of-americas-top-worktech-companies-of-2026-by-time - Named one of America's Greatest Startup Workplaces 2026 https://www.oysterhr.com/library/oyster-2026-newsweek-award by Newsweek - A G2 Spring 2026 Leader https://www.oysterhr.com/library/oyster-named-best-roi-for-any-global-employment-platform-for-g2-spring-2026 across Employer of Record, Global Employment, Multi-country Payroll, and HR Compliance - The only B Corp-certified global employment platform ~ independently verified since 2023 Two of those rankings measured our business impact from the outside. One measured how our own people feel about working here. They landed in the same place ~ because at Oyster, culture and performance aren't separate conversations. They're the same one. And we're just getting started. If you want to do the best work of your career alongside people who care as much as you do, we'd love for you to apply. THE ROLE Location: While this position is posted in a specific location, all of Oyster's positions are fully remote, you can work from home, forever. To create the best experience for our new hire, this role requires you to be based within +3 / -5 UTC. We’re hiring a Lead Product Manager to own the vision, strategy, and outcomes for a critical area of Oyster’s Employer of Record product. You will shape customer-facing experiences, internal tools, and operational workflows that help companies employ talent globally with confidence, compliance, and simplicity. You will work across the full EOR system, not only individual features, to understand how customer needs, country requirements, policies, data, operational processes, and technology interact. You will start with the customer problem and desired business outcome, use direct discovery and first-principles reasoning to identify root causes, and decide whether the best intervention belongs in product, process, policy, Operations, or a combination. You’ll operate independently, making and communicating difficult trade-offs amid ambiguity. You will constructively challenge requested solutions, align senior stakeholders, and connect product decisions to measurable customer, operational, and commercial impact. You will also identify where AI and automation create real value, and where risk or customer needs call for a human in the loop.   KEY RESPONSIBILITIES - Own the product vision, strategy, prioritization, and measurable outcomes for an EOR sub-domain. - Build a systems-level view of customer journeys, internal workflows, policy constraints, data flows, and exceptions across the EOR lifecycle. - Lead direct customer and operational discovery. Separate symptoms and feature requests from underlying problems, and evaluate product, process, policy, and operational interventions before choosing a solution. - Translate strategy into outcome-based roadmaps with clear decisions, learning plans, and success measures. - Work deeply with Operations and AI Engineers to improve scalability, exception handling, service quality, and cost-to-serve, not simply digitize existing processes. - Partner with Engineering and Design from discovery through delivery, using prototypes and technical insight to reduce risk early. - Constructively challenge and align senior stakeholders across Legal, Compliance, Finance, Operations, and Go-to-Market, and communicate strategy, trade-offs, and impact clearly in senior forums. - Contribute repeatable product practices that strengthen discovery, decision quality, and outcome ownership across the Product organization. CORE REQUIREMENTS - 5+ years in Product Management, including demonstrable experience owning a complex product area end-to-end. - 3+ years in HR tech, payroll, benefits, hiring, compliance, or another regulated or operationally complex B2B domain. - Strong systems thinking, with the ability to explain how policy, operations, data, and technology interact, including exceptions and edge cases. - Proven first-principles thinking: the ability to separate the requested feature from the desired outcome and explain why one intervention (product, process, policy, or Operations) was chosen over the alternatives. - Strategic judgment and independence: proven ability to make significant decisions under ambiguity, with explicit trade-offs and a clear view of what was deprioritized. - Deep direct-customer discovery, with examples where conversations with customers and operational teams materially changed the problem definition or planned solution. - Proven ability to constructively challenge, persuade, and align senior stakeholders with competing priorities, and to partner strongly with Operations, Engineering, and Design. - Clear executive communication, with evidence of measurable customer, operational, or commercial impact (e.g. cost-to-serve, cycle time, retention), including the baseline, the change, and how the result was attributed to the decision.   Bonus / Nice-to-Have Experience - EOR, payroll, HR technology, benefits, compliance, fintech, healthcare, logistics, or another regulated and operationally complex domain. Transferable experience counts where the complexity is comparable (multi-country rules, compliance exposure, human-in-the-loop workflows). - Scaling products or workflows across countries, customers, teams, or markets. - Hands-on experience p