Senior Global Benefits Specialist

About the role

This role is centered on managing and optimizing global benefits programs for a platform that assists companies in hiring and paying talent across the world. You will act as a trusted advisor to both customers and internal teams, providing guidance on benefits offerings that are compliant with local regulations and competitive in various international markets. The position involves overseeing benefits design, vendor negotiations, and implementation of new benefits solutions, ensuring a experience for users and stakeholders. This is a one-year fixed-term contract, with an expected conclusion date in August 2027. The role requires a proactive approach to managing benefits across multiple regions, leveraging technology and automation to streamline processes and improve service delivery.

Key facts

What you'll do

• Keep abreast of global benefits trends, legal requirements, and regulatory changes to ensure offerings remain competitive and compliant across all markets.
• Negotiate with international and local benefits brokers to secure optimal coverage, improve service quality, and control costs.
• Lead the implementation of new benefits vendors worldwide, including setting up performance scorecards, conducting quarterly reviews, and managing vendor relationships.
• Address complex benefits questions and escalations from customers and internal teams, providing clear guidance and solutions.
• Support sales efforts by presenting and advising prospective clients on global benefits packages, demonstrating value and compliance.
• Collaborate with internal departments such as legal, compliance, HR, and operations to resolve cross-border benefits challenges and ensure alignment with company policies.
• Develop and maintain an extensive online library of international benefits guides, FAQs, and resources to support internal teams and clients.
• Conduct training sessions for internal teams on multi-country benefits provisions, ensuring they are well-informed and capable of supporting clients effectively.
• Organize webinars and live Q&A sessions to educate clients and internal staff about benefits offerings, updates, and best practices.
• Improve benefits delivery workflows by analyzing current processes, identifying bottlenecks, and implementing automation solutions to shorten response times and enhance service quality.
• AI and automation tools to streamline the creation, updating, and management of country-specific benefits documents, policies, and procedures.
• Analyze benefits ticket data to identify recurring issues, trends, and areas for process improvement, developing preventative solutions to reduce future escalations.
• Maintain a focus on compliance, ensuring all benefits offerings adhere to local laws and regulations, including fringe benefits tax frameworks.
• Support the scaling of benefits programs as the company grows, ensuring processes and systems can handle increased volume and complexity.
• Act as a subject matter expert on international benefits landscapes, sharing insights and best practices with internal teams and clients.
• Assist in the development of benefits-related policies and documentation, ensuring clarity and consistency across regions.
• Participate in cross-functional projects related to HR, legal, and operational initiatives, providing benefits expertise as needed.
• Stay informed about emerging benefits technologies, including AI-driven solutions, to continuously enhance the company's offerings and internal workflows.
• Contribute to a positive team environment by sharing knowledge, supporting colleagues, and maintaining high standards of service delivery.

Requirements

• A minimum of six years of experience in global benefits, including designing, managing, and ensuring compliance across multiple regions.
• Proven track record supporting clients and internal teams across diverse international markets such as AMER, EMEA, APAC, and LATAM.
• Deep understanding of international fringe benefits tax frameworks and how benefit choices impact tax liabilities for both employees and employers.
• Experience working with benefits vendors, negotiating contracts, and managing vendor relationships effectively.
• Strong business acumen, with the ability to balance user needs, cost control, and organizational goals.
• Excellent communication skills, capable of simplifying complex benefits concepts for varied audiences, including clients, internal teams, and leadership.
• Demonstrated stakeholder management skills, including leading quarterly reviews, creating vendor scorecards, and maintaining strong relationships.
• Comfort with HR and benefits technology, including practical experience with AI tools for drafting, research, and data analysis.
• Ability to work in fast-paced, data-driven environments, demonstrating adaptability and proactive problem-solving skills.
• Experience implementing automation workflows within benefits, HR, or operational processes to improve efficiency.
• Background working in a rapidly growing startup or global technology company, with an understanding of scaling benefits programs.
• Reliable internet connection at home to support remote collaboration.
• Fluency in English, with excellent written and verbal communication skills.

Nice to have

• Fluency in additional languages beyond English, especially those relevant to key markets.
• Experience working with Employer of Record (EOR) models and understanding international benefits boundaries and compliance considerations.
• Knowledge of emerging benefits technologies and trends, including AI-driven solutions for benefits management.

Skills & tools

• AI tools for drafting, research, and data analysis, used to streamline benefits documentation and decision-making processes.
• Vendor management and negotiation skills.
• Data analysis skills to interpret benefits ticket data and identify improvement opportunities.
• Familiarity with benefits administration platforms and HRIS systems.

Practical notes

• This is an on-site position based in Spain; candidates must be located within the specified time zones (UTC -1 to UTC +3).
• Oyster provides 40 days of paid time off annually, including holidays and vacation days, with additional days if mandated by local laws.
• Mental health support is available through Plumm, offering resources to support employee wellbeing.
• Employees receive a monthly wellbeing allowance to promote health and wellness.
• New parents are eligible for at least three months of paid leave, with job protection for up to 12 months or as required by local regulations.
• A stipend is provided to support the purchase of a laptop and home office setup, ensuring a productive remote working environment.
• The role involves working in a fast-paced environment, requiring flexibility and proactive engagement with evolving benefits landscapes and technologies.
• The position offers an opportunity to influence global benefits strategies in a rapidly growing company, leveraging automation and AI to improve processes and client satisfaction.