Global Benefits Specialist - Cloudbeds

About Cloudbeds

At Cloudbeds, we're not just building software, we're transforming hospitality. Our platform powers hotels across 150 countries, processing billions in bookings annually. From boutique properties to large 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.

About the Team

Our team supports team members across multiple countries, entities, and employment models. We work 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.

About the Role

We're looking for an experienced, detail-oriented, tech-savvy Cloudbeds teammate to join our Global Payroll & Benefits team. You don't need prior benefits experience — we'll teach you that! What you do need is a solid foundation in operations, confidence working with data, strong problem-solving skills, and the ability to take ownership and follow through independently.

What You'll Do

• Benefits operations: Support enrollments, qualifying life events, status changes, and terminations across Workday, payroll, and vendor platforms, with guidance on unfamiliar or complex cases.
• Data accuracy and reconciliations: 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.
• Team member support: 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.
• Team member education: 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.
• Technology and process improvement: Help test new tools, AI agents, and automated workflows that make everyday processes more efficient.
• Vendor coordination: Work with brokers, insurance carriers, payroll providers, and EOR partners to keep day-to-day benefits operations moving.

Where You'll Grow

As you build your benefits knowledge, you'll have opportunities to get involved in:

• Open enrollment and benefits renewals.
• Retirement programs, including U.S. 401(k) and Canadian RRSP/TFSA/DPSP plans.
• Leave of absence coordination.
• Benefits billing, audits, and vendor invoice projects.
• Country-specific and EOR benefits programs.
• Team member well-being initiatives and other global benefits projects.

What You Bring

• Operations experience: At least 3 years of experience in Customer Success, Support, Finance, Sales Operations, HR, or another operational role. Prior benefits experience is a plus, not a requirement.
• Strong Excel and analytical skills: Comfortable working independently with spreadsheets and data from multiple systems.
• Technology and AI: Hands-on experience using AI tools to improve productivity, analyze information, or simplify workflows, along with curiosity about automation and emerging technologies.
• Communication and creativity: Strong written and verbal communication skills, with experience creating clear presentations, guides, training materials, or other resources.
• Ownership and problem-solving: Proven ability to manage competing priorities, investigate issues, make sound judgments, and follow through independently.
• People-first mindset: A genuine interest in helping people, discretion with confidential information, and the ability to collaborate effectively across functions and countries.