Senior Global Benefits Specialist

✨ 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. Location: While this position is posted in a specific region, 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 that you be based within UTC -1 to UTC +3 This is a one-year fixed-term contract that we anticipate ending in August 2027. In this highly strategic and client-facing role, you’ll be the go-to expert for our customers, team members, and internal teams, shaping and optimizing our global benefits provisions across a diverse portfolio of international markets. As a Senior Specialist, you operate with a high degree of autonomy and commercial acumen. You are the vital connector between our global benefits infrastructure, our internal teams, and our customers. You will balance strategic vendor management (maximizing coverage while minimizing costs) with deep internal and external enablement. You are an advisory benefits expert who loves translating complex provisions into accessible knowledge, hosting highly engaging AMAs, and leveraging modern AI tools to scale your impact on a worldwide scale. This is a one-year fixed-term contract that we anticipate ending in August 2027. Key Responsibilities Strategic Vendor Management & Commercial Optimization Trend Monitoring: Actively monitor macro global benefits trends and multi-regional regulatory shifts to ensure our offerings remain competitive, compliant, and forward-thinking. Vendor Partnerships: Partner effectively with global, regional, and local benefits brokers and vendors, driving negotiations to maximize coverage provisions while aggressively minimizing costs. Governance & Performance: Source and implement new benefits vendors globally. Create robust vendor scorecards, establish tight feedback loops, and lead impactful Quarterly Business Reviews (QBRs) to ensure solid, high-performing partnerships. Client-Facing Advisory & Escalation Support Complex Escalations: Resolve highly complex international benefits queries and escalations that cannot be handled asynchronously by first-line teams. Commercial Support: Join customer and team member calls, including pairing with the Sales team on high-value prospect calls, to confidently present, structure, and advise on our global benefits provisions. Cross-Functional Collaboration: Partner with Customer Support, Sales, Product, and Legal to problem-solve cross-border and country-specific benefits challenges with pragmatic, business-minded solutions. Deep Enablement & Knowledge Management Self-Serve Architecture: Build, own, and maintain a robust global repository of guides, FAQs, and self-serve documentation detailing the intricacies of our international benefits portfolio. Internal Upskilling: Proactively train and upskill internal teams (Support, Sales, etc) to ensure they can confidently discuss multi-country benefits provisions with customers. Interactive Training: Lead high-impact webinars and host live AMA (Ask Me Anything) sessions focused on benefits education for both internal and external audiences worldwide. Continuous Improvement & High Performance Workflow Optimization: Continuously audit and refine global benefits delivery workflows to reduce ticket response times and elevate overall service quality. AI & Automation Integration: Responsibly leverage AI and automation tools to streamline the generation, updating, and scaling of country-specific benefits documentation and processes (eg, renewals) across dozens of regions. Trend Analysis: Analyze recurring benefits ticket data to identify systemic friction points, proactively building preventative resources and product feedback loops. Experience 6+ Years of Global Benefits Experience: Deep expertise in international benefits design,