Remote Global Benefits Specialist

Cloudbeds; Jacksonville (FL); Remote; USD 60,000 - 75,000; Full time

Benefits offered by this job

Remote-first culture

PTO

Fully Paid Parental Leave

Home office stipend

Cloudbeds University access

Professional development

Job summary

Cloudbeds, a fully remote company, seeks an experienced Benefits Operations specialist to join the Global Payroll & Benefits team. You will support enrollments, qualifying life events, status changes, and terminations, coordinating across Workday, payroll, and carrier platforms.

No prior benefits experience required; we’ll train you. You’ll use Excel, AI tools, and automation to improve processes, educate teammates, and deliver virtual benefits orientations.

Qualifications

• Operations experience: At least 3 years in Customer Success, Support, Finance, Sales Ops, HR, or another operational role.
• Strong Excel and analytical skills: able to reconcile data from multiple systems and validate results.
• Technology and AI: hands-on experience using AI tools to improve productivity and workflows.
• Communication and creativity: clear presentations and guides for team members; comfortable presenting to groups.
• Ownership and problem-solving: manage competing priorities and follow through independently.
• People-first mindset: collaborative across functions and diverse teams and respect confidentiality.

Responsibilities

• Benefits operations: support enrollments, life events, status changes, and terminations across Workday, payroll, and vendor platforms.
• Data accuracy and reconciliations: reconcile payroll deductions, enrollment records, and carrier invoices; resolve discrepancies with Payroll, HR, Finance and vendors.
• Team member support: act as a welcoming point of contact for benefits questions and provide updates.
• Team member education: create guides, FAQs, Guru cards, and deliver virtual orientations.
• Technology and process improvement: test new tools, AI agents, and automated workflows.
• Vendor coordination: work with brokers, insurers, payroll providers, and EOR partners to keep operations moving.

Skills

Data analysis

Excel

AI tools

Cross-functional collaboration

Ownership

Tools

Workday

HRIS

Vendor platforms

Job description

Cloudbeds, a fully remote company, seeks an experienced Benefits Operations specialist to join the Global Payroll & Benefits team. You will support enrollments, qualifying life events, status changes, and terminations, coordinating across Workday, payroll, and carrier platforms.

No prior benefits experience required; we’ll train you. You’ll use Excel, AI tools, and automation to improve processes, educate teammates, and deliver virtual benefits orientations.