Senior Director of Product

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, 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.

Core 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.

You'll also need

• A reliable home internet connection (or be able to get one).
• Fluent English language skills.

How we work together at OysterOur values guide the work we do, the decisions we make, and the culture that makes us special. We make it happen. We drive change. We build and give trust, and we are a united team.

Our mission is to create a more equal world, one global hire at a time. Everything we do ladders up to our mission, and that doesn’t just mean building software. We develop programs, participate in workshops, and create dedicated teams to ensure we successfully support companies and knowledge workers in this new world of work.

We embrace asynchronous communication and collaborative work and share our practices in the Oyster Public HQ to help other global teams learn from our experiences.

How YOU workWith diverse locations, cultures, and needs, we created How YOU Work; a program supporting your whole human experience at Oyster:

• 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.

✨ The best jobs should be available to everyone We embrace diverse perspectives and intentionally build our product and company with an inclusive, global mindset. We encourage you to apply, even if you don’t meet every criterion, and are committed to a trust-based, thriving environment.

Oyster is committed to ensuring equal opportunity of employment for qualified persons with disabilities and actively fosters an inclusive work environment. If you require reasonable accommodations throughout the recruiting process, please email jobs@oysterhr.com with the subject line: Interview Accommodations.

Our available positions are on our careers page. Our team will only contact you from an @oysterhr.com email, and we will never ask for money as part of an interview process or job offer. If you receive a suspicious email about Oyster jobs or are directed to a site other than www.oysterhr.com/careers, please report it via our Compliance and Ethics Helpline.