Global Benefits Specialist

𝗪𝗵𝗮𝘁 𝗠𝗮𝗸𝗲𝘀 𝗖𝗹𝗼𝘂𝗱𝗯𝗲𝗱𝘀 𝗨𝗻𝗶𝗾𝘂𝗲

At Cloudbeds, 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 – $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.

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:

• 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.

#LI-REMOTE