Lead Product Manager

✨ 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, you can work from home, forever. To create the best experience for our new hire, this role requires you to be based within +3 / -5 UTC.

We’re hiring a Lead Product Manager to own the vision, strategy, and outcomes for a critical area of Oyster’s Employer of Record product. You will shape customer-facing experiences, internal tools, and operational workflows that help companies employ talent globally with confidence, compliance, and simplicity.

You will work across the full EOR system, not only individual features, to understand how customer needs, country requirements, policies, data, operational processes, and technology interact. You will start with the customer problem and desired business outcome, use direct discovery and first-principles reasoning to identify root causes, and decide whether the best intervention belongs in product, process, policy, Operations, or a combination.

You’ll operate independently, making and communicating difficult trade-offs amid ambiguity. You will constructively challenge requested solutions, align senior stakeholders, and connect product decisions to measurable customer, operational, and commercial impact. You will also identify where AI and automation create real value, and where risk or customer needs call for a human in the loop.

 Key Responsibilities

• Own the product vision, strategy, prioritization, and measurable outcomes for an EOR sub-domain.

• Build a systems-level view of customer journeys, internal workflows, policy constraints, data flows, and exceptions across the EOR lifecycle.

• Lead direct customer and operational discovery. Separate symptoms and feature requests from underlying problems, and evaluate product, process, policy, and operational interventions before choosing a solution.

• Translate strategy into outcome-based roadmaps with clear decisions, learning plans, and success measures.

• Work deeply with Operations and AI Engineers to improve scalability, exception handling, service quality, and cost-to-serve, not simply digitize existing processes.

• Partner with Engineering and Design from discovery through delivery, using prototypes and technical insight to reduce risk early.

• Constructively challenge and align senior stakeholders across Legal, Compliance, Finance, Operations, and Go-to-Market, and communicate strategy, trade-offs, and impact clearly in senior forums.

• Contribute repeatable product practices that strengthen discovery, decision quality, and outcome ownership across the Product organization.

Core Requirements

• 5+ years in Product Management, including demonstrable experience owning a complex product area end-to-end.

• 3+ years in HR tech, payroll, benefits, hiring, compliance, or another regulated or operationally complex B2B domain.

• Strong systems thinking, with the ability to explain how policy, operations, data, and technology interact, including exceptions and edge cases.

• Proven first-principles thinking: the ability to separate the requested feature from the desired outcome and explain why one intervention (product, process, policy, or Operations) was chosen over the alternatives.

• Strategic judgment and independence: proven ability to make significant decisions under ambiguity, with explicit trade-offs and a clear view of what was deprioritized.

• Deep direct-customer discovery, with examples where conversations with customers and operational teams materially changed the problem definition or planned solution.

• Proven ability to constructively challenge, persuade, and align senior stakeholders with competing priorities, and to partner strongly with Operations, Engineering, and Design.

• Clear executive communication, with evidence of measurable customer, operational, or commercial impact (e.g. cost-to-serve, cycle time, retention), including the baseline, the change, and how the result was attributed to the decision.

 Bonus / Nice-to-Have Experience

• EOR, payroll, HR technology, benefits, compliance, fintech, healthcare, logistics, or another regulated and operationally complex domain. Transferable experience counts where the complexity is comparable (multi-country rules, compliance exposure, human-in-the-loop workflows).

• Scaling products or workflows across countries, customers, teams, or markets.

• Hands-on experience prototyping with AI tools or shipping responsible AI- or automation-enabled product experiences.

• Fully distributed and multicultural working experience.

You'll also need

• A reliable home internet connection and fluency in both written and spoken English.

• High standards for quality, ethics, privacy, and compliance in products that affect people and employment.

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 www.oysterhr.com/careers, please report it via our Compliance and Ethics Helpline.

Department: Product Development
Team: Product Management