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Oyster

Automates compliant global hiring and payroll

Lead Product Manager

Product ManagementConfirmed live in the last 24 hours
Full-time

About the Job

Requirements

  • At least 5 years of Product Management experience, including demonstrable ownership of a complex product area end-to-end.
  • At least 3 years of experience in HR technology, payroll, benefits, hiring, compliance, or another regulated or operationally complex B2B domain.
  • Strong systems thinking, including the ability to explain how policy, operations, data, and technology interact, including exceptions and edge cases.
  • Ability to use first-principles reasoning to distinguish requested features from desired outcomes and explain why a product, process, policy, or operational intervention was chosen over alternatives.
  • Proven strategic judgment and independence in making significant decisions under ambiguity, with explicit trade-offs and a clear view of what was deprioritized.
  • Deep direct-customer discovery experience, including examples where customer and operations conversations materially changed the problem definition or planned solution.
  • Proven ability to constructively challenge, persuade, and align senior stakeholders with competing priorities, and to partner with Operations, Engineering, and Design.
  • Clear executive communication and evidence of measurable customer, operational, or commercial impact, including the baseline, the change, and attribution of results to the decision.
  • A reliable home internet connection and fluency in written and spoken English.
  • High standards for quality, ethics, privacy, and compliance in products that affect people and employment.

Responsibilities

  • Own the product vision, strategy, prioritization, and measurable outcomes for an Employer of Record sub-domain.
  • Build a systems-level view of customer journeys, internal workflows, policy constraints, data flows, and exceptions across the Employer of Record lifecycle.
  • Lead direct customer and operational discovery; distinguish symptoms and feature requests from underlying problems; 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 rather than simply digitizing 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.

Desired Qualifications

  • Experience in Employer of Record, payroll, HR technology, benefits, compliance, fintech, healthcare, logistics, or another regulated and operationally complex domain; comparable transferable experience such as multi-country rules, compliance exposure, or human-in-the-loop workflows also counts.
  • Experience 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.
  • Experience working in fully distributed and multicultural settings.

About the Company

Oyster

Automates compliant global hiring and payroll

OysterHR is a global employment platform that helps businesses hire international talent without creating local entities. It automates global hiring by generating compliant employment agreements, activating payroll and benefits, and calculating employment costs instantly, powered by local legal and market intelligence. This enables rapid cross-border hiring and market expansion while ensuring compliance and cost savings. OysterHR differentiates itself by offering an integrated, tech-enabled solution that reduces reliance on external consultants and speeds up onboarding to a matter of days, with claims of leadership in the space and strong customer satisfaction. The company’s goal is to help businesses hire overseas efficiently and compliantly, unlocking access to global talent at lower total costs.

Company size
501-1,000
Company stage
Late Stage VC
Total funding
$288.2M
Headquarters
San Francisco, CA
Founded
2020

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