Global Benefits Specialist

Cloudbeds

. Support enrollments, qualifying life events, status changes, and terminations across Workday, payroll, and vendor platforms .

Posted 11/3/2026full-timeRemote • United StatesMid-LevelSenior💰 $60,000 - $85,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates strong analytical skills and proficiency in Excel to manage and reconcile payroll and benefits data. Capable of creating engaging training materials and presentations while effectively collaborating across functions and managing competing priorities.

Highest-signal resume keywords

Excel ProficiencyAI Tools ExperienceBenefits CoordinationStrong Communication SkillsCustomer Success Experience

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Data ReconciliationPayroll OperationsBenefits AdministrationAnalytical SkillsPresentation CreationWorkflow AutomationIssue InvestigationVirtual Training FacilitationProcess SimplificationHRIS Experience

Soft Skills

CuriosityCollaborationDiscretionIndependenceProblem-Solving

Tools & Technologies

WorkdayAI AgentsAutomation ToolsSpreadsheetsCreative Tools

Industry Keywords

Customer SuccessHR OperationsPayrollBenefits ProgramsGlobal Teams

About the role

Key responsibilities & impact

Support enrollments, qualifying life events, status changes, and terminations across Workday, payroll, and vendor platforms
Reconcile payroll deductions, eligibility files, enrollment records, and carrier invoices
Identify discrepancies, investigate differences, and coordinate with Payroll, HR, Finance, and vendors to resolve them
Serve as a point of contact for benefits questions and own requests from start to finish
Provide clear updates and escalate complex cases when needed
Create benefits guides, FAQs, Guru cards, presentations, and short videos
Help deliver virtual new hire benefits orientations and education sessions
Test new tools, AI agents, and automated workflows
Coordinate with brokers, insurance carriers, payroll providers, and EOR partners
Contribute to open enrollment, benefits renewals, leave of absence coordination, billing, audits, vendor invoice projects, country-specific and EOR benefits programs, and well-being initiatives
Use Excel, AI, automation, and creative tools to simplify processes and reduce repetitive work

Requirements

What you’ll need

At least 3 years of experience in Customer Success, Support, Finance, Sales Operations, HR, or another operational role
Comfortable working independently with spreadsheets and data from multiple systems
Strong Excel and analytical skills
Hands-on experience using AI tools to improve productivity, analyze information, or simplify workflows
Curiosity about automation and emerging technologies
Strong written and verbal communication skills
Experience creating clear presentations, guides, training materials, or other resources for team members
Comfortable presenting to groups or facilitating virtual sessions
Ability to manage competing priorities, investigate issues, make sound judgments, and follow through independently
Genuine interest in helping people
Discretion with confidential information
Ability to collaborate effectively across functions and countries
Currently authorized to work in the location where the position is located without requiring visa sponsorship
Prior benefits experience is not required
Workday or another HRIS, exposure to benefits or payroll operations, experience supporting global teams, creating short videos, or building and testing AI agents and automated workflows are nice to have