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Global Benefits Specialist

3 days, 10 hours ago
Canada
Full-time
Mid Level
Payroll Specialist
Operations
Apply Now
Cloudbeds

Cloudbeds

Cloudbeds provides a top-rated hospitality management system for hotels and properties worldwide, offering seamless operations, revenue optimization, and online booking capabilities to enhance guest experiences and drive revenue growth.

Internet Software & Services
501-1000
Founded 2012
$248M raised
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Description

  • Support 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; investigate and resolve discrepancies.
  • Serve as a primary contact for employee benefits questions, managing requests through resolution and escalating complex cases.
  • Create benefits guides, FAQs, Guru cards, presentations, and short videos, and help deliver virtual orientation and education sessions.
  • Test AI tools, automated workflows, and other technologies to improve operational efficiency.
  • Coordinate day-to-day benefits activities with brokers, carriers, payroll providers, and EOR partners.
  • Contribute to open enrollment, benefits renewals, retirement programs, leave coordination, audits, billing, and global benefits projects as knowledge grows.

Requirements

  • At least 3 years of experience in Customer Success, Support, Finance, Sales Operations, HR, or another operational role.
  • Strong Excel and analytical skills, including reconciling data from multiple systems, investigating discrepancies, and independently validating results.
  • Hands-on experience using AI tools to improve productivity, analyze information, or simplify workflows.
  • Strong written and verbal communication skills, including experience creating guides, presentations, training materials, or other employee resources.
  • Comfort presenting to groups or facilitating virtual sessions.
  • Ability to manage competing priorities, exercise sound judgment, and follow through independently.
  • Discretion when handling confidential information and ability to collaborate across functions and countries.
  • Current authorization to work in the position’s location without visa sponsorship.
  • Experience with Workday or another HRIS, benefits or payroll operations, or supporting global teams (preferred).
  • Experience creating short videos or building and testing AI agents and automated workflows (preferred).

Benefits

  • Remote-first work from eligible locations in Canada, with flexibility to work and travel under company policies.
  • Open PTO beyond statutory minimums, paid Canadian holidays, and 5 paid sick days.
  • Cloudbeds matches 100% of retirement contributions up to 4% of eligible earnings.
  • Extended health, dental, vision, prescription drug, and paramedical coverage for eligible dependents.
  • Company-paid life and AD&D insurance, with disability and critical illness coverage available.
  • Paid maternity and partner leave plus confidential 24/7 Employee Assistance Program support.
  • One-time home office setup stipend and recurring WiFi and phone stipends.
  • Professional development through Cloudbeds University and one paid volunteer day per quarter.

Interested in this position?

Apply directly on the company website

Apply Now

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