Senior Director, Product (Employer of Record)

This a Full Remote job, the offer is available from: North America, EMEA, Canada

✨ 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 EOR employment lifecycle, from onboarding and documentation through time off, benefits, pay and offboarding. That spans the workflows our customers use, the internal tooling our operations teams rely on, and the experience of the employees we employ on our customers' behalf.

This is the core of Oyster's business and it is operationally and legally complex. A payroll delay, a contract issue or a compliance gap becomes a customer escalation, a legal question and an operations fire on the same day. We want someone who treats the whole journey as one experience, for our customers and for the people who have to run it.

As a part of the senior leadership team at Oyster, you will be shaping strategy well beyond your own teams, setting direction across multiple product development teams and trusted to make the calls that define where this part of the business goes. You will be leading through real change: we are raising the bar on performance, moving toward direct feedback and radical candour, and reshaping how we build with AI.

What you will own

• Own the product vision, strategy and roadmap for EOR, and connect team-level work to company outcomes.

• Be accountable for the end-to-end performance of the platform, including the downstream operational reality, not only what ships.

• Turn highly localised, complex regulation into scalable, automated workflows rather than manual workarounds held together by our operations teams.

• Prioritise across new capability, regulatory requirements, technical debt and operational improvement, across several teams at once.

• Coach and grow a team of product managers and group product managers, moving them from delivering features to owning problems and outcomes.

• Partner with Engineering and Design leadership as a real counterpart, holding proper tension on trade-offs without dominating or giving in too easily.

• Partner with Operations, Legal and Finance to shape where this business goes, including the margin and risk picture.

• Build an AI-first way of working in the product organisation: how we discover, prototype and learn, not just what we ship.

What we are looking for

• 10+ years in product management, including 5 to 7 years leading other product managers, with measurable business and customer outcomes behind you.

• Experience in operationally or legally complex B2B or Fintech. HR tech, EOR, payroll or compliance is ideal, though the complexity matters more to us than the sector.

• A systems thinker who starts from first principles and diagnoses before proposing.

• Hands-on experience using AI to change how your team works, not only what it ships. We will ask what decision changed because of something you learned.

• Able to set product vision at business-unit level and generate real buy-in when priorities shift.

• Proven people leadership: coaching product managers into leaders, holding a clear bar, having the difficult conversation early.

• Experience leading through structural change, and comfort with ambiguity as an opportunity rather than a risk.

• Communication strong enough to influence senior stakeholders, backed by a mechanism that turns agreement into delivery.

You'll also need

• A reliable home internet connection, or be able to get one.

• Fluent English language skills.

How we work together at Oyster

Our values guide the work we do, the decisions we make, and the culture that makes Oyster what it is. We make it happen—progress is our default setting. We drive change, we build and give trust, and we move as one united team.

Our mission is to create a more equal world of work: helping companies everywhere hire, pay, and care for talent anywhere. Everything we do ladders up to our mission. We embrace asynchronous, collaborative work and share how we operate in the Oyster Public HQ so other global teams can learn from us.

How YOU work

With 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 to spend on a wide range of options.

• 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 please report it via our Compliance and Ethics Helpline.