Senior Global Benefits Specialist - Oyster

About Oyster

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.

Distributed across 60+ countries since 2020, we're proof that a high-performing culture doesn't need an office.

Note: This is a one-year fixed-term contract ending in November 2027. This role requires you to be based within UTC -1 to UTC +3.

The Role

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 will 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.

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 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 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 across dozens of regions.
• Trend Analysis: Analyze recurring benefits ticket data to identify systemic friction points, proactively building preventative resources and product feedback loops.

Requirements

• 6+ Years of Global Benefits Experience: Deep expertise in international benefits design, compliance, and vendor management with a strong track record of supporting internal stakeholders and external corporate clients across multiple continents.
• True Cross-Country Expertise: Direct hands-on experience navigating nuanced benefits landscapes, statutory requirements, and local market norms across multiple global regions (e.g., AMER, EMEA, APAC, LATAM).
• Tax Knowledge: Strong foundational knowledge of international fringe benefits tax (FBT) frameworks and how country-specific benefit choices impact employee and employer tax liabilities.
• Commercial Mindset: Highly commercial in your ways of working; able to balance end-user empathy with rigorous cost management and business objectives.
• Communication Skills: Exceptional written and verbal communication, with the ability to translate technical benefits terminology into clear advice.
• Stakeholder Management: Proven success running QBRs, constructing vendor scorecards, and managing matrixed relationships.
• Tech-Forward: Practical experience using modern AI tools to accelerate research, drafting, and data analysis.
• Technical Environment: Background working in a fast-scaling startup or global tech environment.
• General: Reliable home internet connection and fluent English proficiency.

Bonus Qualifications

• Professional fluency in multiple languages.
• Demonstrable experience working within or closely with an Employer of Record (EOR) model.
• Proven experience implementing AI tools or automated workflows within an HR or Ops function.

What We Offer

• Work from anywhere: Fully remote environment with no borders or physical HQ.
• Paid time off: 40 days off per year (including holidays and vacation), or more if required by your country.
• Mental health support: Access to Plumm, our mental well-being service.
• Wellbeing allowance: Monthly allowance provided via ThanksBen wallet.
• Flexible parental leave: At least three months’ paid leave for all new parents.
• WFH stipend: Stipend provided for your laptop and home office setup.