Global Benefits Specialist

Contract type
Ongoing
Work mode
Remote
Experience
Mid-level · 3+ years

Job description

An operations-focused role on Cloudbeds' Global Payroll & Benefits team, supporting benefits enrollments, data reconciliations, team member support and process improvement. It is aimed at experienced operations professionals without requiring prior benefits experience.

At a glance

Employment
Full-time · Employee (employment agreement)
Work mode
Remote
Pay
USD 60,000 – 85,000 / year

What you'll do

  • Support enrollments, qualifying life events, status changes, and terminations across Workday, payroll, and vendor platforms, with guidance on unfamiliar or complex cases
  • 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
  • Be a welcoming, reliable point of contact for benefits questions; own requests from start to finish, providing clear updates and escalating complex cases when needed
  • Create benefits guides, FAQs, Guru cards, presentations, and short videos that make complicated information easier to understand; help deliver virtual new hire benefits orientations and education sessions
  • Help test new tools, AI agents, and automated workflows that make everyday processes more efficient
  • Work with brokers, insurance carriers, payroll providers, and EOR partners to keep day-to-day benefits operations moving

What we're looking for

  • At least 3 years of experience in Customer Success, Support, Finance, Sales Operations, HR, or another operational role
  • Strong Excel and analytical skills: comfortable working independently with spreadsheets and data from multiple systems, reconciling information, investigating discrepancies, and validating results without step-by-step guidance
  • Hands-on experience using AI tools to improve productivity, analyze information, or simplify workflows, along with curiosity about automation and emerging technologies
  • Strong written and verbal communication skills, with experience creating clear presentations, guides, training materials, or other resources; comfortable presenting to groups or facilitating virtual sessions
  • Proven ability to manage competing priorities, investigate issues, make sound judgments, and follow through independently
  • A genuine interest in helping people, discretion with confidential information, and the ability to collaborate effectively across functions and countries

Nice to have

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

Your team

Global Payroll & Benefits

Supports team members across multiple countries, entities, and employment models, working closely with HR, Finance, brokers, insurance carriers, payroll providers, and Employer of Record (EOR) partners to keep payroll and benefits accurate, compliant, and focused on the team member experience.

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About Cloudbeds

We're not just building software, we're transforming hospitality.

Cloudbeds' platform powers hotels across 150 countries, processing billions in bookings annually. From boutique properties to large hotel groups, it helps hoteliers transform operations and uplevel their commercial strategy through a unified platform that integrates with hundreds of partners. Founded in 2012, Cloudbeds is a fully remote team of 650+ team members across 40+ countries.

Key facts

  • 650+ team members
  • 2012
  • Hospitality technology
  • Platform powers hotels across 150 countries
  • Processing billions in bookings annually
  • Fully remote team with teammates in 40+ countries
  • Team speaks 30+ languages
  • Winner – Hotel Management Software | HotelTechAwards (2026)
  • Overall 10 Best Places to Work | HotelTechAwards (2026)
  • Overall Top 10 Hotelier's Choice | HotelTechAwards (2026)
  • Finalist – Property Management Systems (PMS) & Channel Managers | HotelTechAwards (2026)
  • Most Loved Workplace® Certified (2024)
  • Deloitte Technology Fast 500 (2024)

What they value

  • Grit
  • Kaizen
  • Discovery
  • Stronger Together
  • Welcoming
  • Presence
  • Mop Bucket Attitude
  • Positive Intent