Senior Manager, Product Design

✨ 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 +2 /-6 UTC.

As the Senior Manager, Product Design, you will lead, inspire, and scale a distributed team of Product Designers and UX Researchers. You will own the design vision for Oyster’s platform, ensuring our complex global employment workflows feel intuitive, seamless, AI-native, and deeply human.

A critical focus of this role will be pioneering our next-generation design workflows. You will champion the strategic adoption of AI within the design organization, optimizing how we research, prototype, and build, while guiding your team in architecting intuitive UI, Zero-UI, and agentic experiences for our customers.

Key Responsibilities

• Team Leadership & Scaling: Lead and scale a high-performing team of Product Designers and UX Researchers, fostering a culture of rigorous feedback, continuous learning, and psychological safety.
• Talent Development: Define clear career ladders, provide actionable coaching, and elevate execution across both generative UX research methodologies and high-fidelity interaction design.
• AI-Augmented Design Ops: Drive the internal adoption of emerging AI and automated tooling within the design lifecycle (e.g., AI-assisted prototyping, automated UI generation, and LLM-driven research synthesis) to exponentially maximize team velocity.
• Agentic & Data-Driven UX: Partner with Product and Engineering to define how AI elegantly enhances the Oyster user experience, translating complex global compliance, tax, and payroll data into proactive, multi-modal, and agentic workflows.
• System Evolution: Modernize our Design Ops and scale our global design system to seamlessly integrate automated, intelligent tokenization and intelligent layout generation.
• Cross-Functional Alignment: Serve as a strategic peer to Engineering, Product, GTM, and Data/AI leaders to align UX strategy with business growth, data model capabilities, and technical feasibility.
• Guardianship of Trust: Establish design principles for responsible AI, transparency, and data privacy, ensuring automated workflows maintain user trust in a high-stakes compliance environment.

Core Requirements

• 8+ years of experience in product or UX design, with a proven portfolio of complex, data-heavy B2B SaaS or fintech environments.
• 4+ years of formal people management experience, ideally leading distributed, multi-timezone teams.
• AI Literacy: Deep, demonstrable curiosity and hands-on experience utilizing GenAI tooling to optimize product development workflows and systems.
• Systems Thinker: Strong foundational knowledge in designing for non-linear user journeys, asynchronous AI states, and conversational/agentic interfaces.
• [BONUS] Experience navigating compliance-heavy, highly regulated industries (Fintech, HRTech, LegalTech).
• [BONUS] Experience mapping complex service blueprints where software and human service operations overlap harmoniously.

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.