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Oyster is a global employment platform enabling companies to hire, pay, and support talent anywhere in the world. As Senior Director of Product for the Employer of Record (EOR) offering, you will own the complete product vision, strategy, and execution across the full employment lifecycle—from onboarding and documentation through time off, benefits, pay, and offboarding. This role sits at the core of Oyster's business and encompasses customer workflows, internal operations tooling, and the employee experience for people employed on customers' behalf.
You will be part of Oyster's senior leadership team, shaping strategy across multiple product development teams and making decisions that define the direction of this business unit. The role requires navigating operationally and legally complex challenges: payroll delays, contract issues, and compliance gaps directly impact customer escalations, legal considerations, and operational priorities simultaneously. You will lead through significant change, including raising performance standards, implementing direct feedback and radical candor, and embedding AI-first ways of working.
Key responsibilities include:
- Owning the product vision, strategy, and roadmap for EOR, connecting team-level work to company outcomes
- Holding accountability for end-to-end platform performance, including downstream operational reality
- Translating highly localized, complex regulation into scalable, automated workflows rather than manual processes
- Prioritizing across new capabilities, regulatory requirements, technical debt, and operational improvements across multiple teams
- Coaching and developing product managers and group product managers, moving them from feature delivery to outcome ownership
- Partnering with Engineering and Design leadership as a true counterpart, managing trade-offs thoughtfully
- Collaborating with Operations, Legal, and Finance to shape business direction, including margin and risk considerations
- Building an AI-first product organization: how the team discovers, prototypes, and learns
Oyster is fully distributed across 60+ countries, ranked #10 on TIME and Statista's 2026 list of America's Top WorkTech Companies, named a Newsweek America's Greatest Startup Workplace 2026, and is the only B Corp-certified global employment platform.
REQUIREMENTS:
- 10+ years in product management, including 5–7 years leading other product managers, with measurable business and customer outcomes
- Experience in operationally or legally complex B2B or Fintech environments; HR tech, EOR, payroll, or compliance experience is ideal, though operational/legal complexity is the priority
- Systems thinker who starts from first principles and diagnoses before proposing solutions
- Hands-on experience using AI to change how your team works, not only what it ships; you should be able to articulate decisions that changed because of AI-driven learning
- Ability to set product vision at business-unit level and generate real buy-in when priorities shift
- Proven people leadership: coaching product managers into leaders, maintaining clear performance bars, and addressing difficult conversations early
- Experience leading through structural change with comfort treating ambiguity as opportunity
- Communication skills strong enough to influence senior stakeholders, with a track record of turning agreement into delivery
- Reliable home internet connection
- Fluent English language skills
