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.