Cloudbeds

Hospitality

GlobalBenefitsSpecialist

$75–110k ~AI est. North America Remote Friendly
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for Mid+ candidates.

The Brief

“Global Benefits Specialist at Cloudbeds. Skills: Global benefits, Benefits administration, Leave management, Retirement programs. Process enrollments. Process qualifying life events”

Industry & Context.

Hospitality
Problems you'll solve

Troubleshoot enrollment; Troubleshoot billing; Troubleshoot eligibility; Troubleshoot vendor issues; Investigate discrepancies; Problem-solving

What They're Looking For.

Must Have

3–5 years benefits administration, 3–5 years HR operations, 3–5 years payroll operations, Foundational knowledge U.S. benefits, Experience supporting employee-facing benefits, Attention to detail, Comfortable presenting information, Written and verbal communication, Manage confidential information, Comfortable working remote

Nice to Have

Benefits programs across multiple countries, Retirement and savings programs, Retirement plan audits, Compliance testing, Annual filings, Vendor management, Employer of Record (EOR) provider, HRIS experience, Workday, Vendor coordination experience, High-growth or global startup, CEBS, PHR, or equivalent certification

What You'll Do.

Process qualifying life events

Process status changes

Maintain accurate benefits records

Identify discrepancies

Coordinate with brokers

Coordinate with carriers

Coordinate with payroll providers

Coordinate with EOR partners

Support open enrollment

Facilitate new hire orientations

Facilitate employee education

Create employee-facing materials

Maintain benefits guides

Maintain presentations

Support renewal preparation

Support utilization reporting

Support global retirement programs

Support Canadian RRSP/TFSA/DPSP

Coordinate retirement plan providers

Coordinate retirement plan brokers

Coordinate retirement plan Payroll

Coordinate retirement plan Finance

Assist with retirement plan audits

Assist with compliance reviews

Assist with annual filings

Maintain retirement procedures

Maintain retirement documentation

Serve as employee contact

Troubleshoot enrollment issues

Troubleshoot billing issues

Troubleshoot eligibility issues

Troubleshoot vendor issues

Escalate complex cases

Review eligibility files

Review enrollment data

Investigate discrepancies

Support audit readiness

Support compliance documentation

Support leave of absence programs

Support parental leave

Support disability leave

Support medical leave

Coordinate leave administration vendors

Coordinate leave timelines

Maintain awareness of leave compliance

Support benefits processes international

Assist with documentation

Assist with process improvement

Identify process improvements

Help maintain standardized procedures

Help maintain internal documentation

How You'll Work.

Team & Collaboration

Partner with Payroll; Partner with HR; Partner with Finance; Partner with brokers; Partner with insurance carriers; Partner with payroll vendors; Partner with EOR providers; Work cross-functionally

Communication Scope

Employee communications; Employee education; Presenting information; Written communication; Verbal communication

Full Job Description

What Makes Us Unique At Cloudbeds, we're not just building software, we’re transforming hospitality. Our intelligently designed platform powers properties across 150 countries, processing billions in bookings annually. From independent properties to hotel groups, we help hoteliers transform operations and uplevel their commercial strategy through a unified platform that integrates with hundreds of partners. And we do it with a completely remote team. Imagine working alongside global innovators to build AI-powered solutions that solve hoteliers' biggest challenges. Since our founding in 2012, we've become the World's Best Hotel PMS Solutions Provider and landed on Deloitte's Technology Fast 500 again in 2024 but we're just getting started. We’re looking for a Global Benefits Specialist to help support and scale benefits operations across a globally distributed workforce spanning multiple countries, entities, and employment models. This role combines global benefits administration, leave coordination, employee support, reconciliations, compliance, and cross-functional operational work. You’ll partner closely with Payroll, HR, Finance, brokers, insurance carriers, payroll vendors, and Employer of Record (EOR) providers to help ensure employees around the world receive accurate, timely, and well-supported benefits experiences. This is an excellent opportunity for someone looking to grow their career in global benefits. You'll gain exposure to benefits administration, retirement programs, leave management, vendor partnerships, compliance, and employee education across multiple countries and employment models within a fast-growing global SaaS company. About the Team Our Global Payroll Process enrollments, qualifying life events, status changes, and terminations across HRIS, payroll, and vendor platforms; Maintain accurate benefits records and identify discrepancies across systems; Coordinate with brokers, carriers, payroll providers, and EOR partners on day-to-day adminis

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