[Hiring] Global Benefits Specialist @Cloudbeds

Role Description

Do you enjoy turning messy data into clear answers, finding smarter ways to work, and making complicated information easy to understand? Are you someone who picks up new tools quickly, enjoys experimenting with AI, and genuinely likes helping others?

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.

Coming from Customer Success, Support, Sales Operations, Finance, or another operational team? Your experience could translate well into global benefits, and we'd love to hear from you!

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

• 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. You can reconcile information, investigate discrepancies, and validate your results without needing step-by-step guidance.
• 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 for team members. Comfortable presenting to groups or facilitating virtual sessions.
• 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.

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.

What We Value

• Grit: We are resilient, driven, and determined to find solutions and move forward.
• Kaizen: We believe in continuous improvement, learning, and growing every day.
• Discovery: We stay curious, open-minded, and always explore new ideas and better ways of working.
• Stronger Together: We collaborate, support one another, and achieve more as one global team.
• Welcoming: We value diversity, inclusion, respect, and creating a place where everyone belongs.
• Presence: We speak up, take ownership, show initiative, and lead regardless of title.
• Mop Bucket Attitude: We roll up our sleeves, solve problems, and step in wherever needed to help the team succeed.
• Positive Intent: We assume the best in each other, communicate openly, and approach situations with empathy and trust.

What You'll Gain

• A path into a global benefits career.
• Opportunities to bring AI, automation, and creative ideas into real projects.
• Exposure to HR, Payroll, Finance, Legal, and external partners across multiple countries.
• Practical learning opportunities and room to grow in a fully remote company with teammates in 40+ countries.

Compensation

Depending on your skills and experience, you can expect your annual compensation to be between $60,000 – $85,000 USD. (The salary is only for US-based candidates).

Work Authorization

Please note that applicants must be currently authorized to work in the location where the position is located without requiring visa sponsorship. At this time, Cloudbeds is unable to provide sponsorship for work visas.