Global Benefits Specialist

Overview

This role supports global payroll and benefits operations by turning complex, changing information into accurate outcomes for team members. The position involves managing benefits enrollment workflows, reconciling data across systems, and coordinating with internal teams and external partners to keep processes compliant and moving.

Responsibilities

• Benefits operations: Support enrollments, qualifying life events, status changes, and terminations across Workday, payroll, and vendor platforms, with guidance on unfamiliar or complex cases.
• Data accuracy and reconciliations: Reconcile payroll deductions, eligibility files, enrollment records, and carrier invoices. Identify discrepancies, investigate differences, and follow through with Payroll, HR, Finance, and vendors to resolve them.
• Team member support: Serve as a welcoming, reliable point of contact for benefits questions. Own requests from start to finish, providing clear updates and escalating complex cases when needed.
• Team member education: Create benefits guides, FAQs, “Guru cards,” presentations, and short videos to make complicated information easier to understand. Help deliver virtual new hire benefits orientations and education sessions.
• Technology and process improvement: Help test new tools, AI agents, and automated workflows that make everyday processes more efficient.
• Vendor coordination: Work with brokers, insurance carriers, payroll providers, and Employer of Record (EOR) partners to keep day-to-day benefits operations moving.

Opportunities for Growth

As you build your benefits knowledge, you may get involved in:

• Open enrollment and benefits renewals
• Retirement programs, including U.S. 401(k) and Canadian RRSP/TFSA/DPSP plans
• Leave of absence coordination
• Benefits billing, audits, and vendor invoice projects
• Country-specific and EOR benefits programs
• Team member well-being initiatives and other global benefits projects

Requirements

• Operations experience: At least 3 years of experience in Customer Success, Support, Finance, Sales Operations, HR, or another operational role. Prior benefits experience is a plus, not a requirement.
• Strong Excel and analytical skills: Comfortable working independently with spreadsheets and data from multiple systems. Able to reconcile information, investigate discrepancies, and validate results without step-by-step guidance.
• Technology and AI: Hands-on experience using AI tools to improve productivity, analyze information, or simplify workflows; curiosity about automation and emerging technologies.
• Communication and creativity: Strong written and verbal communication skills with experience creating clear presentations, guides, training materials, or other resources for team members. Comfortable presenting to groups or facilitating virtual sessions.
• Ownership and problem-solving: Proven ability to manage competing priorities, investigate issues, make sound judgments, and follow through independently.
• People-first mindset: Genuine interest in helping people, discretion with confidential information, and ability to collaborate effectively across functions and countries.

Preferred Qualifications

• Experience with Workday or another HRIS
• Exposure to benefits or payroll operations
• Experience supporting global teams
• Experience creating short videos
• Experience building and testing AI agents and automated workflows

Compensation & Benefits

• Annual compensation: $60,000 – $85,000 USD (salary only applies to US-based candidates)
• PTO: In accordance with local labor requirements
• Parental leave: Fully paid parental leave
• Home office stipend: Based on country of residency
• Professional development: Professional development courses in Cloudbeds University; access to professional development including manager training, upskilling, and knowledge transfer
• Remote work: Remote First, Remote Always

Work Authorization

Applicants must be currently authorized to work in the location where the position is located without requiring visa sponsorship. At this time, sponsorship for work visas is not available.

Location

Remote (team members support multiple countries).