Senior Director of Product

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Oyster

WebsiteLinkedInAll Job Openings

501 - 1000 employees

Founded 2020

🤝 B2B

👥 HR Tech

☁️ SaaS

B2B • HR Tech • SaaS

Oyster® is an automated global employment platform that simplifies the process of hiring and managing international talent. With coverage in 180+ countries, Oyster provides solutions for global payroll, compliance, employee benefits, and talent mobility, allowing companies to onboard and manage both full-time employees and contractors efficiently. By leveraging deep local knowledge and expert guidance, Oyster helps businesses navigate the complexities of international hiring and scaling their workforce globally.

📋 Description

• 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, and retain a high-performing, bar-raising, remote-first Product team, ensuring the organization has the talent and capability to execute our long-term product strategy.

🎯 Requirements

• 10+ years of experience in Product Management, including 5+ years in a leadership role managing other Product Managers, with a strong track record of driving measurable business and Customer outcomes across complex product domains. • 4+ years of experience in HR tech, EoR, payroll, compliance, or B2B SaaS, with deep familiarity with regulated or operationally complex environments. • Demonstrated ability to set and communicate product vision and strategy at a product or business-unit level, connecting team-level work to company outcomes. • Strong track record as a systems thinker, with a proven ability to take highly complex, localized regulations and turn them into scalable, automated, agentic product workflows. • Proven people leadership skills, with experience coaching and developing Product Management talent, building high-performing teams, and creating clarity in ambiguous environments. • Experience leading multi-layered product organizations, including managing and developing other product leaders. • Proven track record of hiring and developing "bar-raising" talent, turning individual contributors into strong leaders and leaving teams significantly stronger than you found them. • Strong product discovery and problem-framing skills, with the ability to synthesize Customer pain points, market signals, and operational data into an impactful product strategy. • Hands-on experience driving AI-powered and automation-driven product initiatives, including defining use-cases, evaluating trade-offs, and measuring real-world impact. • Highly data-driven, with the ability to operate at both the strategic and analytical levels. • Comfortable operating in ambiguity, with a proactive, ownership-driven mindset and the ability to bring clarity and structure across a multi-team domain. • High standards for quality, ethics, and transparency, particularly when building products that directly impact people's 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 HQ. As long as work is timely, your team is supported, and you're 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 a wide range of options; see the benefits catalogue for ideas. • Flexible parental leave: All new parents are eligible for at least three months’ 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 get you set up quickly.