Senior Director of Product

This is a fully remote position, open to applicants in Europe.

📋 Description

• Responsible for the comprehensive performance and strategic alignment of the EoR platform, ensuring it achieves measurable business impact and customer outcomes throughout the entire employment lifecycle.

• Lead prioritization, ensure delivery integrity, and foster cross-functional alignment with company objectives, taking charge of translating strategy into scalable, outcome-oriented product execution.

• Drive highly complex, business-critical product and platform initiatives, successfully navigating executive alignment and securing executive buy-in to turn the EoR product’s strategic vision into clear, measurable company outcomes.

• Directly oversee, nurture, and expand a team of Product Managers, establishing a high standard for product craft, discovery, and delivery.

• Manage prioritization across the product, balancing new features, regulatory obligations, technical debt, and operational enhancements across various teams and roadmaps.

• Convert product strategy into actionable execution, collaborating with Product Managers to outline clear roadmaps, outcomes, and success metrics at both team and domain levels.

• Collaborate closely with Engineering and Design leadership to deliver high-quality, scalable solutions with an excellent user experience across both teams.

• Work alongside leaders in Operations, Finance, and Legal to influence broader company strategy, ensuring the platform aligns with overall business and margin objectives.

• Represent the EoR, Contractors, and related areas at the strategic leadership level, effectively communicating strategy, trade-offs, progress, risks, and impacts.

• Utilize data and insights to guide product-level decisions, assess impact, and promote continuous improvement.

• Contribute to the larger Product organization, shaping best practices, enhancing product quality, and assisting in the development of a robust product-led culture.

• Cultivate an AI-first culture within the Product organization, rethinking our product development lifecycles to optimize operational velocity and scalability.

• Build, motivate, and retain a high-performing, bar-raising, remote-first Product team, ensuring the organization possesses the talent and capabilities to implement our long-term product strategy.

⛳️ Requirements

• 10+ years of experience in Product Management, including 5+ years in a leadership role overseeing other Product Managers, with a proven track record of achieving measurable business and customer outcomes across complex product domains.

• 4+ years of experience in HR tech, EoR, payroll, compliance, or B2B SaaS, with a deep understanding of regulated or operationally intricate environments.

• Proven ability to set and articulate product vision and strategy at a product or business-unit level, connecting team-level efforts to company outcomes.

• Strong history as a systems thinker, with a demonstrated capacity to transform highly complex, localized regulations into scalable, automated, agentic product workflows.

• Proven leadership skills, with experience coaching and developing Product Management talent, building high-performing teams, and providing clarity in ambiguous situations.

• Experience managing multi-layered product organizations, including mentoring and developing other product leaders.

• Successful track record in hiring and nurturing "bar-raising" talent, enabling individual contributors to evolve into strong leaders and enhancing team effectiveness.

• Strong product discovery and problem-framing capabilities, with the ability to synthesize customer pain points, market signals, and operational data into a compelling product strategy.

• Hands-on experience in driving AI-powered and automation-driven product initiatives, including defining use cases, evaluating trade-offs, and measuring tangible impacts.

• Highly data-oriented, capable of operating at both strategic and analytical levels.

• Comfortable navigating ambiguity, with a proactive, ownership-driven approach and the ability to introduce clarity and structure across a multi-team domain.

• High standards for quality, ethics, and transparency, especially when developing products that directly affect individuals' employment, compensation, and compliance.

• Proven experience in scale-up or high-growth environments, balancing speed, quality, and long-term sustainability across multiple teams and workstreams.

🏝️ Benefits

• Work from anywhere: Oyster has no borders or headquarters. As long as your work is timely, your team is supported, and you are authorized to work where you live, you can work from anywhere.

• Paid time off: Enjoy 40 days off per year (including holidays and vacation), or more if required by your country.

• Mental health support: Access Plumm, our mental well-being service.

• Wellbeing allowance: Each month, receive a wellbeing allowance in your ThanksBen wallet. Spend it on various options; refer to the benefits catalogue for ideas.

• Flexible parental leave: All new parents are eligible for at least three months of paid leave, with job protection for up to 12 months or as required locally.

• WFH stipend: Receive a stipend for your laptop and home office equipment to facilitate a quick setup.