Remote Global Benefits Operations Specialist

Third-Party Job Posts; United States; Remote; USD 60,000 - 75,000; Full time

Benefits offered by this job

Remote-first culture

Home office stipend

Paid parental leave

PTO in line with local laws

Job summary

Cloudbeds, a fully remote company transforming hospitality software, seeks a detail-oriented benefits operations specialist. You’ll own tasks from enrollments to vendor invoicing, ensuring data accuracy across Workday and payroll platforms while learning benefits processes.

You’ll use Excel and AI tools to streamline workflows, create guides and videos, and educate teammates. This role supports global teams and offers strong growth in a fully remote environment.

Qualifications

• 3+ years in an operational role (Customer Success, Support, Finance, Sales Ops, HR, etc.).
• Strong Excel and analytical skills with spreadsheets and data from multiple systems.
• Hands-on experience using AI tools to improve productivity or workflows.
• Clear written and verbal communication; ability to present to groups.
• Ownership mindset; ability to manage priorities and follow through independently.
• People-first mindset with discretion handling confidential information.

Responsibilities

• Support enrollments, life events, status changes, and terminations across Workday and vendor platforms; guide on complex cases.
• Reconcile payroll deductions, eligibility files, enrollment records, and carrier invoices; investigate discrepancies with Payroll/HR/Finance.
• Be a welcoming point of contact for benefits questions; own requests from start to finish with clear updates.
• Create benefits guides, FAQs, Guru cards, and short videos; deliver virtual new hire benefits orientations.
• Test new tools, AI agents, and automated workflows to improve efficiency.
• Coordinate with brokers, insurance carriers, payroll providers, and EOR partners to keep operations moving.

Skills

Excel

Analytical skills

AI tools

Communication

Ownership

Problem-solving

People-first mindset

Tools

Workday

Job description

Cloudbeds, a fully remote company transforming hospitality software, seeks a detail-oriented benefits operations specialist. You’ll own tasks from enrollments to vendor invoicing, ensuring data accuracy across Workday and payroll platforms while learning benefits processes.

You’ll use Excel and AI tools to streamline workflows, create guides and videos, and educate teammates. This role supports global teams and offers strong growth in a fully remote environment.