[All remote jobs](https://jobicy.com/jobs.md)[![Cloudbeds logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/3aef1a38-221.png)](https://jobicy.com/company/cloudbeds.md)[Cloudbeds](https://jobicy.com/company/cloudbeds.md) # Global Benefits Specialist AI Summary Cloudbeds is hiring a Global Benefits Specialist to support benefits administration for a distributed workforce across multiple countries and employment models. The role handles enrollments, life events, payroll and eligibility reconciliations, vendor coordination, and employee support. The specialist will create clear benefits education materials, facilitate virtual orientations, and help improve workflows through Excel, AI, and automation. Candidates need at least three years of operational experience, strong analytical judgment, discretion, and the ability to work independently across HR, Payroll, Finance, and external partners. This is a growth-oriented HR operations role where prior benefits experience is helpful but not mandatory.[Apply for this job](#job-application)[View company](https://jobicy.com/company/cloudbeds.md)ShareRemote from[USA](https://jobicy.com/job-region/usa.md), [Canada](https://jobicy.com/job-region/canada.md)SalaryUSD 60k–75k / yrDepartment[HR & Recruiting](https://jobicy.com/categories/hr.md)EmploymentFull TimeExperienceSeniorPublished7 Nov 2026Apply before7 Dec 2026Listing views58Application actions3Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. Opportunity details ## About this role. What Makes [Cloudbeds](https://jobicy.com/company/cloudbeds.md) Unique At [Cloudbeds](https://www.cloudbeds.com/), we’re not just building software, we’re transforming hospitality. Our platform powers hotels across 150 countries, processing billions in bookings annually. From boutique properties to large hotel groups, we help hoteliers transform operations and uplevel their commercial strategy through a unified platform that integrates with hundreds of partners. And we do it with a completely remote team. Imagine working alongside global innovators to build AI-powered solutions that solve hoteliers’ biggest challenges. Since our founding in 2012, we’ve continually been recognized for excellence, most recently earning top honors at the 2026 HotelTechAwards for Best Hotel Management Software and landing on Deloitte’s Technology Fast 500 again, but we’re just getting started. About the Team Our team supports team members across multiple countries, entities, and employment models. We work closely with HR, Finance, brokers, insurance carriers, payroll providers, and Employer of Record (EOR) partners to keep payroll and benefits accurate, compliant, and focused on the team member experience. We value accuracy, collaboration, continuous improvement, and finding practical ways to make complex processes simpler for everyone. About the Role 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 As you build your benefits knowledge, you’ll have opportunities to get involved in: * 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. 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. 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, 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. * 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 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 – $75,000 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. 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](https://www.cloudbeds.com/) Cloudbeds [Awards](https://www.cloudbeds.com/press/?press_type=company-news&news_category=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) Discover our Benefits: * Remote First, Remote Always * PTO in accordance with local labor requirements * Fully Paid Parental Leave * Home office stipend based on country of residency * Professional development courses in Cloudbeds University * Access to professional development, including manager training, upskilling, and knowledge transfer Everyone is Welcome – A Culture of Inclusion Cloudbeds is proud to be an Equal Opportunity Employer that celebrates the diversity in our global team! We do not discriminate based upon race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics. Cloudbeds is committed to the full inclusion of all qualified individuals. As part of this commitment, Cloudbeds will ensure that persons with disabilities are provided reasonable accommodations in the hiring process. We encourage deaf, hard-of-hearing, deaf-blind, and deaf-disabled individuals to apply. If reasonable accommodation is needed to participate in the job application or interview process or to perform essential job functions, please contact our HR team by phone at (858) 201-7832 or via email at accommodations@cloudbeds.com. Cloudbeds will provide an American Sign Language (ASL) interpreter where needed as a reasonable accommodation for the hiring process. To all Staffing and Recruiting Agencies: Our Careers Site is only for individuals seeking a job at Cloudbeds. Staffing, recruiting agencies, and individuals being represented by an agency are not authorized to use this site or to submit applications, and any such submissions will be considered unsolicited. Cloudbeds does not accept unsolicited resumes or applications from agencies. Please do not forward resumes to our jobs alias, Cloudbeds employees, or any other company location. Cloudbeds is not responsible for any fees related to unsolicited resumes/applications. Show more [Apply now >](https://jobicy.com/jobs/159466-global-benefits-specialist.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 3/5EasyHard ### Pace & Pressure 4/5RelaxedFast-paced ### Autonomy Level 4/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThe role requires accurate reconciliation across HRIS, payroll, carriers, and EOR partners while handling confidential employee matters. Benefits expertise can be learned, but independent investigation, data validation, and cross-functional follow-through are essential. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Market rate$67,500US market range (per year)$60k–$85k0$93.50k AI insightThe employer explicitly states annual compensation of $60,000–$75,000 USD for US-based candidates. The estimated US annual market range for a benefits operations specialist with the stated operational and global-support scope is $60,000–$85,000 USD. ## Core skills Skills and capabilities most closely associated with this opportunity. [Benefits administration](https://jobicy.com/jobs?search_keywords=Benefits%20administration.md)[Payroll reconciliation](https://jobicy.com/jobs?search_keywords=Payroll%20reconciliation.md)[Excel](https://jobicy.com/jobs?search_keywords=Excel.md)[Data analysis](https://jobicy.com/jobs?search_keywords=Data%20analysis.md)[HR operations](https://jobicy.com/jobs?search_keywords=HR%20operations.md)[Workday](https://jobicy.com/jobs?search_keywords=Workday.md)[Vendor coordination](https://jobicy.com/jobs?search_keywords=Vendor%20coordination.md)[Employee support](https://jobicy.com/jobs?search_keywords=Employee%20support.md)[Process improvement](https://jobicy.com/jobs?search_keywords=Process%20improvement.md)[AI tools](https://jobicy.com/jobs?search_keywords=AI%20tools.md)[Automation](https://jobicy.com/jobs?search_keywords=Automation.md)[Employee communications](https://jobicy.com/jobs?search_keywords=Employee%20communications.md)[Cross-functional collaboration](https://jobicy.com/jobs?search_keywords=Cross-functional%20collaboration.md)[Confidentiality](https://jobicy.com/jobs?search_keywords=Confidentiality.md) Sample interview questionsHow would you investigate a discrepancy between payroll deductions and a benefits carrier invoice?I would compare employee eligibility, enrollment effective dates, deduction records, and invoice line items using a structured reconciliation file. I would identify the root cause, validate the required correction with the relevant HR, Payroll, or vendor contact, document the outcome, and confirm that the correction is reflected in the next cycle. Describe how you would explain a complex benefits process to a new employee. I would first identify the employee's decision or action required, then explain the process in plain language with clear deadlines and examples. I would supplement the discussion with a concise guide or FAQ, confirm understanding, and provide a clear channel for follow-up questions. What steps would you take to protect confidential employee benefits information? I would use approved systems and access controls, share only the minimum necessary information, verify recipients before sending records, and avoid discussing sensitive details in unsecured channels. I would also follow established retention, documentation, and escalation procedures for any suspected privacy issue. How have you used Excel or another tool to improve an operational process? I would describe building a standardized reconciliation tracker using formulas, validation rules, and exception flags to reduce manual review. The goal would be to make discrepancies visible early, create an auditable process, and give stakeholders a consistent status view. How do you prioritize multiple employee requests and time-sensitive operational tasks? I assess urgency, employee impact, legal or payroll deadlines, and dependencies, then organize work into a visible queue with clear owners and due dates. I communicate early when priorities conflict, provide status updates, and escalate complex issues before they jeopardize deadlines. Next step ## Apply now. Follow the employer’s application method and review Jobicy’s safety guidance before sharing personal information. 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