Senior Manager, Product Design

The best jobs are often restricted to a few wealthy cities, but talent exists everywhere. Oyster set out to change this by launching a global employment platform that enables companies to hire, pay, and support talent anywhere.

We’re proof that a strong, engaged culture doesn't require an office. Since January 2020, Oyster has:

🌏 Built a distributed team of 400+ across 60+ countries

👩‍💻 Featured in Forbes as #9 in FlexJobs Top 30 Companies for remote jobs

🌈 Formed a diverse leadership team and a workforce that’s 60% female

🏆 Earned top employee engagement scores

🦄 Raised $286 million; valued at $1.2 billion

💚 Achieved B Corp status in 2023

Our momentum shows the power of global employment, and we’re just getting started! If you want to help us drive change and work remotely, we’d love for you to apply!

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.

• 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.

• 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.

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

• Fluent English language skills.

Our 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.

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. 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.

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 [email protected] 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.