Regional HR & People Operations Specialist at Cloudbeds in Canada

What Makes Us Unique At Cloudbeds, we're not just building software, we’re transforming hospitality. Our intelligently designed platform powers properties across 150 countries, processing billions in bookings annually. From independent properties to 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 become the World's Best Hotel PMS Solutions Provider and landed on Deloitte's Technology Fast 500 again in 2024 but we're just getting started. We are seeking a highly organized, proactive, detail-oriented, and collaborative Regional HR & People Operations Specialistto support our growing People organization across the United States and Canada. This role will serve as a critical operational partner supporting: NORAM HRBPs; People Operations; Managers; and team members across the region. The ideal candidate thrives in a fast-paced, highly collaborative, globally distributed environment and enjoys balancing operational execution, employee support, compliance coordination, HR systems administration, process improvement, and cross-functional partnership. This role is instrumental in helping ensure smooth employee lifecycle management, strong operational execution, leave administration, HR compliance, and an exceptional team member experience throughout the NORAM region. This is an excellent opportunity for someone looking to deepen their experience in regional HR. Our People Team We’re a globally distributed, multicultural People Team spanning North America, Latin America, EMEA, and APAC, and that global footprint isn’t just a fact; it’s a strength we fully embrace. Our team brings a rich blend of perspectives, experiences, and cultural fluency that fuels everything we do, from nuanced people strategies to inclusive systems and scalable processes that work for everyone, everywhere. We collaborate with heart and hustle. Despite time zones and borders, we operate with high trust, clear communication, and deep mutual respect. Whether we’re partnering with hiring managers, leading HR transformation, supporting regional teams, or crafting intentional team member experiences, we show up for each other and for the people we serve! This is a team where empathy meets execution. Where people who thrive are those who are curious, proactive, globally minded, and genuinely passionate about making Cloudbeds a place where every team member can do their best work. We’re not just People Team, we’re culture shapers, problem solvers, strategy supporters, and people-first builders. What You’ll Do: Regional HR & Team Member Support Serve as a primary point of contact for day-to-day HR-related inquiries from team members and managers across NORAM; Provide timely updates, guidance, and support related to HR policies, handbooks, processes, systems, employee lifecycle events, PTO, leave tracking, and general People operations; Support employee experience initiatives and help foster a positive, collaborative, and people-first environment; Escalate sensitive or complex matters appropriately to HRBPs, Legal, Payroll, Benefits, or leadership when needed; Assist with employee communications, documentation, follow-ups, and coordination of People Team initiatives. Responsible for coordinating quarterly NORAM coffee breaks, regional holiday initiatives, and employee engagement activities to foster team connection, culture, and a positive employee experience within the region. HRBP Partnership & Operational Support Partner closely with NORAM HRBPs to support operational execution of regional people strategies and organizational initiatives; Assist HRBPs with organizational changes, promotions, compensation updates, transfers, restructures, and employee lifecycle administration; Support preparation of documentation, reporting, employee communications, organizational data, and operational tracking required by HRBPs and leadership; Help coordinate HR processes tied to performance cycles, talent reviews, engagement initiatives, manager support, and workforce planning activities; Support operational follow-up and coordination related to employee relations matters, documentation, and internal processes as directed by HRBPs; Act as a strong operational liaison between HRBPs, Payroll, Benefits, People Operations, Talent Acquisition, Finance, and Business Systems teams. People Operations & HR Administration Manage and coordinate employee lifecycle processes, including: onboarding; offboarding; internal transfers; compensation changes; promotions; status changes; manager changes; organizational updates; relocations and system maintenance; Ensure all employee records, documentation, and HR systems remain accurate, updated, and compliant; Maintain digital personnel files and confidential HR documentation with a high degree of integrity and discretion; Support process documentation, SOP creation, internal knowledge base updates, and operational workflows; Contribute to continuous process improvement initiatives focused on scalability, automation, efficiency, and employee experience. Payroll & Benefits Coordination Partner closely with Payroll and Benefits teams to ensure timely and accurate employee data processing; Support payroll readiness activities, including: compensation updates; status changes; PTO balances; leave tracking; timesheet coordination; and employee data audits; Leave of Absence (LOA) Administration & Compliance Coordinate administrative support and tracking for Leave of Absence programs across NORAM, including: FMLA; Provincial Stat Leaves beside FMLA to include Canadian leave references ADA accommodations; Canadian LOAs along with ADA: Provincial Human Rights Codes and Duty to Accommodate parental leaves; state/provincial leave programs; and other protected leaves; Maintain accurate leave documentation and ensure proper tracking within internal systems; Coordinate communication between employees, managers, Payroll, Benefits, HRBPs, and external vendors when applicable; Support compliance tracking and operational execution related to leave management processes. HRIS, Reporting & Data Integrity Maintain and update employee data within Workday and related HR systems; Ensure integrity, accuracy, and consistency of organizational, payroll, compensation, PTO, and benefits-related data; Generate recurring and ad hoc reports for HRBPs, People leadership, Payroll, Finance, and other stakeholders; Assist with audits, data reconciliations, reporting requests, and compliance documentation; Partner with Business Systems teams to troubleshoot HRIS discrepancies and improve workflows and automation opportunities; Support reporting and analytics requests related to headcount, employee changes, compliance, turnover, and People metrics. Support HRBPs with all people operations tasks for the region. Compliance & Risk Management Maintain a strong foundational understanding of: U.S. federal employment laws; state employment regulations; Canadian provincial labor standards; and HR operational compliance requirements; Ensure HR ops and data handling align with PIPEDA; Support audits, documentation requests, compliance reporting, and policy administration activities; Help ensure operational processes align with internal policies and external legal requirements; Assist with maintaining compliance records and documentation across NORAM; Support operational coordination tied to investigations, accommodations, and sensitive HR matters when applicable. Projects & Cross-Functional Collaboration Participate in regional and global People Team projects and operational initiatives; Help improve operational efficiency, scalability, documentation, and employee experience processes; Collaborate across HR, Payroll, Benefits, Finance, IT, Talent Acquisition, and Business Systems teams on ongoing initiatives; Support implementation and optimization of People systems, workflows, and operational processes; Assist with organizational readiness efforts tied to growth, restructuring, policy changes, and operational scaling. What Sets You Up for Success: Required Qualifications Bachelor’s degree in Human Resources, Business Administration, or related field (or equivalent practical experience); 3+ years of experience in: HR Operations; People Operations; HR Generalist; HR Specialist; or HR Coordination roles; Strong understanding of: U.S. employment laws; HR operational best practices; employee lifecycle administration; and compliance processes; Familiarity with Canadian employment standards and provincial labor regulations strongly preferred; Experience supporting HRBPs, regional HR functions, or People Operations teams; Experience coordinating payroll, benefits, leave administration, or employee data management; Hands-on experience with HRIS platforms (Workday strongly preferred); Strong Excel and data management skills; Excellent organizational skills and attention to detail; Strong written and verbal communication skills in English; Ability to manage highly sensitive and confidential information with professionalism and discretion; Comfortable working independently within a remote, asynchronous, and globally distributed environment; Strong prioritization, problem-solving, and follow-through skills. Preferred Qualifications Experience working in global SaaS, technology, hospitality tech, or high-growth companies; Experience supporting multi-state U.S. populations and/or Canadian employees; Experience partnering closely with Payroll and Benefits teams; Experience supporting remote/distributed organizations; Process improvement and project coordination experience; PHR or SHRM-CP certification preferred; Experience working within fast-paced scaling environments preferred. Compensation: Depending on your skills and experience, you can expect your annual compensation to be between $65,000 – $80,000 USD. #LI-SD1 What to Expect - Your Journey with Us Behind Cloudbeds' revolutionary technology is a team of redefining what's possible in hospitality. We're 650+ employees across 40+ countries, bringing together elite engineers, AI architects, world-class designers, 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 Company Awards to Check Out! Best All-In-One Hotel Management System | HotelTechAwards (2025) Overall 10 Best Places to Work | HotelTechAwards (2025) Most Loved Workplace® Certified (2024) Top 10 People’s Choice(2024) Deloitte Technology Fast 500 (2024) Discover our Benefits: Remote First, Remote Always PTO in accordance with local labor requirements Monthly Wellness Fridays - enjoy an extra long weekend every month Full 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 processes. 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