Global Benefits Specialist

Cloudbeds; Philadelphia (Philadelphia County); Remote; USD 60,000 - 75,000; Full time

Benefits offered by this job

Remote First, Remote Always

PTO per local labor laws

Fully Paid Parental Leave

Home office stipend by country

Cloudbeds University development

Manager training and knowledge sharing

Job summary

Cloudbeds is a fully remote company seeking a Global Benefits Operations teammate with a strong operations background and data-driven mindset. You'll support enrollments, manage data accuracy across Workday and vendor platforms, and educate team members through clear resources.

Ideal candidates have 3+ years in an operational role, strong Excel skills, and a curiosity for AI and automation. Remote, global role with opportunities to impact benefits across 40+ countries.

Qualifications

• At least 3 years of experience in a operational role (Customer Success, Support, Finance, Sales Ops, HR, or similar).
• Strong Excel and analytical skills with ability to reconcile data across systems.
• Hands-on experience using AI tools to improve productivity or automate workflows.
• Clear, written and verbal communication; ability to create guides and training materials.
• Demonstrated ownership, problem-solving, and ability to manage competing priorities.

Responsibilities

• Benefits operations: Support enrollments, events, status changes, and terminations across Workday, payroll, and vendor platforms.
• Data accuracy and reconciliations: Reconcile payroll deductions, eligibility files, enrollment records, and carrier invoices; resolve discrepancies with multiple teams.
• Team member support: Serve as a reliable point of contact for benefits questions; own requests end-to-end.
• Team member education: Create guides, FAQs, Guru cards, and training materials; deliver virtual orientations.
• Technology and process improvement: Test new tools, AI agents, and automated workflows to increase efficiency.
• Vendor coordination: Work with brokers, insurance carriers, payroll providers, and EOR partners.

Skills

Excel

Analytical skills

Data analysis

AI tools

Communication

Ownership

Tools

Workday

HRIS

Payroll platforms

Vendor platforms

Job description

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.

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.

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!

• 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.

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.

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.

• 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.

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.

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.
• 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

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.

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

• 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)
• 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

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 [phone] or via email at [e-mail]. Cloudbeds will provide an American Sign Language (ASL) interpreter where needed as a reasonable accommodation for the hiring process.