Lead Product Manager, Employer of Record (EOR) Product

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 prototyping with AI tools or shipping responsible AI- or automation-enabled product experiences.
• Fully distributed and multicultural working experience.

You'll also need

• A reliable home internet connection and fluency in both written and spoken English.
• High standards for quality, ethics, privacy, and compliance in products that affect people and employment.