Regional HR & People Operations Specialist

Third-Party Job Posts

13h • $65,000 - $80,000 • Remote

About The Position

At Cloudbeds, we're transforming hospitality by powering properties in 150 countries with our intelligently designed platform. We are seeking a highly organized, proactive, detail-oriented, and collaborative Regional HR & People Operations Specialist to 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.

Requirements

• 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.

Nice To Haves

• 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.

Responsibilities

• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.

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.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level