Remote Global Benefits & AI Operations Specialist

Third-Party Job Posts; Oregon; Hybrid; USD 60,000 - 75,000; Full time

Benefits offered by this job

Remote First

PTO in accordance with local labor req

Fully Paid Parental Leave

Home office stipend

Professional development Cloudbeds

Access to professional development

Job summary

Cloudbeds is a fully remote company seeking a specialist to join the Global Payroll & Benefits team. You will support enrollments, reconciliations, and employee inquiries, helping ensure accurate payroll and benefits administration across multiple countries.

The role emphasizes data-driven processes, AI tooling, and clear team communications, with opportunities to improve workflows, educate teammates, and collaborate with brokers, carriers, and EOR partners.

Qualifications

• 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.
• 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.
• Workday or another HRIS, exposure to benefits or payroll operations, experience supporting global teams, creating short videos, or building and testing AI agents and automated workflows.

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

Operations experience

Excel

Analytical skills

AI tools experience

Data reconciliation

Tools

Workday

HRIS

Job description

Cloudbeds is a fully remote company seeking a specialist to join the Global Payroll & Benefits team. You will support enrollments, reconciliations, and employee inquiries, helping ensure accurate payroll and benefits administration across multiple countries.

The role emphasizes data-driven processes, AI tooling, and clear team communications, with opportunities to improve workflows, educate teammates, and collaborate with brokers, carriers, and EOR partners.