Cloudbeds - Global Benefits Specialist
Requirements
• 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. • Technology and AI • 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. • Communication and creativity • Ownership and problem-solving: Proven ability to manage competing priorities, investigate issues, make sound judgments, and follow through independently. • Ownership and problem-solving • People-first mindset: A genuine interest in helping people, discretion with confidential information, and the ability to collaborate effectively across functions and countries. • People-first mindset • Nice to have: 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. • What We Value • At Cloudbeds, our values shape how we work, collaborate, and grow together: • Grit: We are resilient, driven, and determined to find solutions and move forward. • Grit: • Kaizen: We believe in continuous improvement, learning, and growing every day. • Kaizen: • Discovery: We stay curious, open-minded, and always explore new ideas and better ways of working. • Discovery: • Stronger Together: We collaborate, support one another, and achieve more as one global team. • Stronger Together: • Welcoming: We value diversity, inclusion, respect, and creating a place where everyone belongs. • Welcoming • Presence: We speak up, take ownership, show initiative, and lead regardless of title. • Presence • Mop Bucket Attitude: We roll up our sleeves, solve problems, and step in wherever needed to help the team succeed. • Mop Bucket Attitude • Positive Intent: We assume the best in each other, communicate openly, and approach situations with empathy and trust. • Positive Intent • What You'll Gain • What You'll Gain
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.
Benefits
• 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. • Data accuracy and reconciliations • 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 support: • 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. • Team member education • Technology and process improvement: Help test new tools, AI agents, and automated workflows that make everyday processes more efficient. • Technology and process improvement: • Vendor coordination: Work with brokers, insurance carriers, payroll providers, and EOR partners to keep day-to-day benefits operations moving. • Vendor coordination: • Where You'll Grow • Where You'll Grow • As you build your benefits knowledge, you'll have opportunities to get involved in: • 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. • Technology, the Practical Way • We're excited about finding smarter ways to work. You'll use Excel, AI, automation, and creative tools to simplify processes, turn complex benefits topics into engaging team member resources, and reduce repetitive work. • 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 • Interested? • Thinking about your next step at Cloudbeds? We'd love to hear from you! Apply through the internal posting and tell us what interests you about the role. • 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. • Work Authorization: • What to Expect - Your Journey with Us • Behind Cloudbeds' revolutionary technology is a team redefining what's possible in hospitality. We're 650+ team members across 40+ countries, bringing together elite engineers, AI architects, world-class designers, hoteliers, and hospitality veterans to solve challenges others haven't dared to tackle. Our diverse team speaks 30+ languages, but we all share one language: a passion for innovation and travel. From pioneering breakthroughs in machine learning to revolutionizing how hotels operate, we're not just watching the future of hospitality unfold – we're coding it, designing it, writing it, and shipping it. If you're ready to work alongside some of the brightest minds in tech who are obsessed with using AI to transform a trillion-dollar industry, this is your chance to be part of something extraordinary. • Learn more online at cloudbeds.com • Cloudbeds Awards: • Cloudbeds Awards: • Winner – Hotel Management Software | HotelTechAwards (2026) • Overall 10 Best Places to Work | HotelTechAwards (2026) • Overall Top 10 Hotelier's Choice | HotelTechAwards (2026) • Finalist – Property Management Systems (PMS) & Channel Managers | HotelTechAwards (2026) • Most Loved Workplace® Certified (2024) • Deloitte Technology Fast 500 (2024) • Remote First, Remote Always • PTO in accordance with local labor requirements • Fully Paid Parental Leave • Professional development courses in Cloudbeds University • Access to professional development, including manager training, upskilling, and knowledge transfer • Everyone is Welcome - A Culture of Inclusion
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