Global Benefits Specialist

This is a fully remote position, open to applicants in North America.

📋 Description

• Assist with benefits enrollments, qualifying life events, status changes, and terminations across Workday, payroll, and vendor platforms.

• Reconcile payroll deductions, eligibility files, enrollment records, and carrier invoices.

• Detect discrepancies, investigate differences, and collaborate with Payroll, HR, Finance, and vendors to resolve issues.

• Act as a dependable point of contact for benefits inquiries and manage requests from initiation to completion.

• Develop benefits guides, FAQs, Guru cards, presentations, and short videos.

• Aid in delivering virtual new-hire benefits orientations and educational sessions.

• Evaluate new tools, AI agents, and automated workflows to enhance efficiency.

• Collaborate with brokers, insurance carriers, payroll providers, and EOR partners.

• Participate in open enrollment, benefits renewals, retirement programs, leave coordination, billing, audits, vendor invoice projects, country-specific and EOR benefits programs, as well as well-being initiatives.

⛳️ Requirements

• Minimum of 3 years of experience in Customer Success, Support, Finance, Sales Operations, HR, or a comparable operational role.

• Proficient in working independently with spreadsheets and data from various systems.

• Capable of reconciling information, investigating discrepancies, and verifying results autonomously.

• Practical experience utilizing AI tools to enhance productivity, analyze data, or streamline workflows.

• Interest in automation and emerging technologies.

• Excellent written and verbal communication skills.

• Experience developing clear presentations, guides, training materials, or other resources for team members.

• Comfortable presenting to groups or leading virtual sessions.

• Demonstrated ability to manage competing priorities, investigate issues, make informed decisions, and follow through independently.

• Genuine passion for assisting others.

• Ability to handle confidential information with discretion.

• Proven capacity to collaborate effectively across functions and countries.

• Prior experience in benefits is not mandatory; familiarity with Workday or another HRIS, benefits or payroll operations, global team support, short-video creation, and experience with AI agents/automated workflows are advantageous.

• Applicants must currently be authorized to work in the location of the position without requiring visa sponsorship.

🏝️ Benefits

• Remote First, Remote Always.

• PTO in accordance with local labor regulations.

• Fully Paid Parental Leave.

• Home office stipend based on country of residency.

• Access to professional development courses through Cloudbeds University.

• Opportunities for professional growth, including manager training, upskilling, and knowledge transfer.