Remote Global Benefits Specialist

Cloudbeds; Philadelphia (Philadelphia County); Remote; USD 60,000 - 75,000; Full time

Benefits offered by this job

Remote First, Remote Always

PTO per local labor laws

Fully Paid Parental Leave

Home office stipend by country

Cloudbeds University development

Manager training and knowledge sharing

Job summary

Cloudbeds is a fully remote company seeking a Global Benefits Operations teammate with a strong operations background and data-driven mindset. You'll support enrollments, manage data accuracy across Workday and vendor platforms, and educate team members through clear resources.

Ideal candidates have 3+ years in an operational role, strong Excel skills, and a curiosity for AI and automation. Remote, global role with opportunities to impact benefits across 40+ countries.

Qualifications

• At least 3 years of experience in a operational role (Customer Success, Support, Finance, Sales Ops, HR, or similar).
• Strong Excel and analytical skills with ability to reconcile data across systems.
• Hands-on experience using AI tools to improve productivity or automate workflows.
• Clear, written and verbal communication; ability to create guides and training materials.
• Demonstrated ownership, problem-solving, and ability to manage competing priorities.

Responsibilities

• Benefits operations: Support enrollments, events, status changes, and terminations across Workday, payroll, and vendor platforms.
• Data accuracy and reconciliations: Reconcile payroll deductions, eligibility files, enrollment records, and carrier invoices; resolve discrepancies with multiple teams.
• Team member support: Serve as a reliable point of contact for benefits questions; own requests end-to-end.
• Team member education: Create guides, FAQs, Guru cards, and training materials; deliver virtual orientations.
• Technology and process improvement: Test new tools, AI agents, and automated workflows to increase efficiency.
• Vendor coordination: Work with brokers, insurance carriers, payroll providers, and EOR partners.

Skills

Excel

Analytical skills

Data analysis

AI tools

Communication

Ownership

Tools

Workday

HRIS

Payroll platforms

Vendor platforms

Job description

Cloudbeds is a fully remote company seeking a Global Benefits Operations teammate with a strong operations background and data-driven mindset. You'll support enrollments, manage data accuracy across Workday and vendor platforms, and educate team members through clear resources.

Ideal candidates have 3+ years in an operational role, strong Excel skills, and a curiosity for AI and automation. Remote, global role with opportunities to impact benefits across 40+ countries.