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 500+ 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 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, compliance, and vendor management with a strong track record of supporting both 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).
Strong foundational knowledge of international fringe benefits tax (FBT) frameworks and how country-specific benefit choices impact employee and employer tax liabilities.
Commercial & Solution-Oriented Mindset: Highly commercial in your ways of working; able to balance empathy for the end-user with rigorous cost management and business objectives.
Exceptional Communication & Presentation Skills: A natural educator who can translate intricate, technical benefits terminology into clear, accessible advice—both in writing and when presenting live to clients or senior leaders.
Stakeholder & Relationship Management: Proven success running QBRs, constructing vendor scorecards, and managing complex matrixed relationships across vendors, customers, and internal departments.
Tech-Forward & AI-Literate: Digitally savvy with a strong curiosity for HR tech. Practical experience using AI tools to accelerate drafting, research, and data analysis is highly valued.
Growth-Driven & Change-Ready: Thrives in a fast-paced, metrics-driven environment; comfortable navigating ambiguity and eager to move operations from reactive firefighting to proactive scaling.
AI Implementation: Proven experience implementing AI tools or automated workflows specifically within a benefits, HR, or Ops function.
Fast-Paced Environments: Background working in a fast-scaling startup or global tech environment.
[BONUS] Additional Languages: Professional fluency in multiple languages is a strong plus.
[BONUS] EOR Experience: Demonstrable experience working within or closely with an Employer of Record (EOR) model, navigating international benefits boundaries.
You'll also need
A reliable home internet connection (or be able to get one)
Fluent English language
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
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