Senior Director, Product (Employer of Record)

✨ 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 Named one of America's Greatest Startup Workplaces 2026 by Newsweek A G2 Spring 2026 Leader 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, and you can work from home. Forever. To create the best experience for our new hire, this role requires you to be based within -5 / +3 UTC. As Senior Director of Product for our Employer of Record offering, you will own the product vision, strategy, and execution across the full employer of record (EoR) lifecycle. We are looking for a Senior Director of Product to serve as the strategic leader of our core business. This spans customer-facing workflows, internal tooling, and employee-facing experiences that enable companies around the world to hire, onboard, pay, and manage their global workforce efficiently, compliantly, and at scale. This leader will treat the entire Customer journey, from onboarding documentation collection through time off, benefits, pay, and offboarding, as a single seamless experience for our customers and our team members. We’re looking for an AI-first product leader comfortable applying creativity and first-principles thinking to solve real Customer and operational problems across a complex, regulated domain. You’ll bring strong product judgment, a structured approach to problem-solving, and the ability to balance user needs, regulatory complexity, and business outcomes, while leading and developing a team of product managers to do the same. You'll set direction across multiple Product Development (Product, Design, and Engineering) teams, leading complex, cross-functional initiatives that require close collaboration across Legal, Compliance, Finance, Operations, and Go-To-Market. Strong ownership, clear communication, and the ability to drive alignment and momentum at a senior level are critical to success. Key Responsibilities Accountable for the end-to-end performance and strategic alignment of the EoR platform, ensuring it delivers measurable business impact and Customer outcomes across the full employment lifecycle. Own prioritization, delivery integrity, and cross-functional alignment to company objectives, with responsibility for translating strategy into scalable, outcome-driven product execution. Spearhead highly complex, business-critical product and platform initiatives, successfully navigating executive alignment and securing executive buy-in to translate the EoR product’s strategic vision into definitive, measurable company outcomes. Directly manage, develop, and grow a team of Product Managers, setting a high bar for product craft, discovery, and delivery. Drive prioritization across the product, balancing new features, regulatory requirements, tech debt, and operational improvements across multiple teams and roadmaps. Translate product strategy into execution, working with Product Managers to define clear roadmaps, outcomes, and success metrics at the team and domain level. Partner closely with Engineering and Design leadership to deliver high-quality, scalable solutions with strong user experience across both teams. Partner with leaders across Operations, Finance, and Legal to shape broader company strategy, ensuring the platform supports overall business and margin goals. Represent the EoR, Contractors, and connected areas at the strategic leadership level, clearly communicating strategy, trade-offs, progress, risks, and impact. Use data and insights to inform product-level decisions, measure impact, and drive continuous improvement. Contribute to the wider Product organization, shaping best practices, raising the bar for product quality, and helping build a strong product-led culture. Foster an AI-first culture within the Product organization, reimagining our product development lifecycles to maximize operational velocity and scalability. Build, inspire,