Global Benefits Specialist — Remote, AI-Driven Ops

Cloudbeds; Atlanta (GA); Remote; USD 60,000 - 75,000; Full time

Benefits offered by this job

Remote First

PTO per local laws

Fully Paid Parental Leave

Home office stipend

Professional development

Job summary

Cloudbeds is seeking an experienced, detail-oriented operations professional to join our Global Payroll & Benefits team. You’ll own benefits operations, data accuracy, and team member support while learning benefits concepts on the fly.

This remote role values analytical thinking, ownership, and the ability to explain complex topics clearly to teammates across countries. Your work will involve using Workday and other HRIS, testing AI-powered workflows, and guiding open enrollment, vendor

Qualifications

• Operations experience: At least 3 years of experience in Customer Success, Support, Finance, Sales Operations, HR, or another operational role.
• 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.
• Communication and creativity: Strong written and verbal communication skills, with experience creating clear presentations, guides, training materials, or other resources for team members.
• 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.

Responsibilities

• 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.

Skills

Data analysis

Excel

AI tools

Communication

Tools

Workday

HRIS

Job description

Cloudbeds is seeking an experienced, detail-oriented operations professional to join our Global Payroll & Benefits team. You’ll own benefits operations, data accuracy, and team member support while learning benefits concepts on the fly.

This remote role values analytical thinking, ownership, and the ability to explain complex topics clearly to teammates across countries. Your work will involve using Workday and other HRIS, testing AI-powered workflows, and guiding open enrollment, vendor