Global Benefits Specialist

Defining the future of work & living globally

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

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.

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)

Discover Our Canada Benefits

At Cloudbeds, we believe great work deserves great benefits. Here's how we support your well-being, growth, and life beyond work.

#RemoteFirst:

Work from home in eligible locations across Canada, with flexibility to work and travel in accordance with company policies.

Time Off & Wellness:

Open PTO beyond statutory minimums, paid Canadian holidays, and 5 paid sick days.

Retirement Savings:

Cloudbeds matches 100% of your contributions, up to 4% of eligible earnings.

Health, Dental & Vision:

Extended healthcare coverage, including prescription drugs, dental, vision, and paramedical services for you and your eligible dependents.

Life & Disability Protection:

Company-paid Life & AD&D insurance (3x annual earnings, up to $500,000), with disability and critical illness coverage also available.

Family & Mental Health:

Paid maternity and partner leave, plus confidential 24/7 Employee Assistance Program (EAP) support.

Home Office Support:

A one-time home office setup stipend and recurring WiFi and phone stipends.

Growth & Community:

Professional development through Cloudbeds University and 1 paid Volunteer Day per quarter through Cloudbeds Cares.

Benefits are subject to eligibility requirements and plan terms.

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 View phone number on click.appcast.io or via email at View email address on click.appcast.io. Cloudbeds will provide an American Sign Language (ASL) interpreter where needed as a reasonable accommodation for the hiring process.