Senior Director of Product (Employer of Record) - Fully Remote

As Senior Director of Product for Oyster’s Employer of Record (EOR) offering, you will own the product vision, strategy, and execution across the full EOR employment lifecycle—from onboarding and documentation through time off, benefits, pay, and offboarding. This spans customer workflows, internal tooling for operations teams, and the experience of employees hired on behalf of Oyster’s customers.

The EOR business is operationally and legally complex. A payroll delay, contract issue, or compliance gap can escalate into a customer crisis, legal question, and operations emergency simultaneously. You’ll treat the entire journey as one seamless experience for both customers and employees.

As part of Oyster’s senior leadership team, you’ll shape strategy beyond your teams, setting direction across multiple product development groups and making pivotal decisions that define this business’s trajectory. You’ll lead transformative change, including raising performance standards, adopting direct feedback and radical candor, and integrating AI-first workflows into product development.

What You Will Own

• Define and execute the product vision, strategy, and roadmap for EOR, aligning team-level work with company-wide outcomes.
• Ensure end-to-end platform performance, addressing both what ships and the operational realities downstream.
• Convert highly localized, complex regulations into scalable, automated workflows—eliminating manual workarounds reliant on operations.
• Prioritize across new capabilities, regulatory requirements, technical debt, and operational improvements across multiple teams simultaneously.
• Coach and develop a team of product managers and group product managers, transitioning them from feature delivery to owning problems and outcomes.
• Collaborate with Engineering and Design leadership as a true partner, balancing trade-offs without dominating or capitulating.
• Partner with Operations, Legal, and Finance to shape the business’s direction, including margin and risk considerations.
• Embed an AI-first approach into product operations—focusing on discovery, prototyping, and learning, not just delivery.

What We Are Looking For

• 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, ideally in HR tech, EOR, payroll, or compliance—though complexity trumps sector specificity.
• A systems thinker who starts from first principles, diagnosing challenges before proposing solutions.
• Hands-on AI experience that transforms how your team operates—not just what it produces. Be prepared to articulate decisions shaped by AI-driven insights.
• Ability to set business-unit-level product vision and secure buy-in even when priorities shift.
• Proven leadership in coaching product managers into leaders, maintaining clear expectations, and delivering tough conversations early.
• Experience leading through structural change and comfort with ambiguity as an opportunity, not a risk.
• Strong communication skills to influence senior stakeholders and translate agreement into execution.

Additional Requirements:

• A reliable home internet connection or the ability to secure one.
• Fluent English language skills.