Senior People Operations – Learning Specialist

This is a fully remote position, open to applicants in Canada.

📋 Description

• Take ownership of Canadian People Operations along with the operational implementation and upkeep of global learning initiatives.

• Oversee the Canadian employee lifecycle, which includes onboarding, changes in employment, leaves of absence, offboarding, and documentation related to employment.

• Manage Canadian payroll through Rippling by reviewing inputs and deductions, addressing discrepancies, and ensuring accurate payroll records are maintained.

• Administer Canadian benefits, which encompasses enrollment, responding to employee inquiries, and supporting renewals.

• Act as the first point of contact for routine employee inquiries while escalating complex issues related to employee relations, legal matters, or policy concerns.

• Manage the learning platform, coordinating course setup, assignments, testing, completion tracking, and reporting.

• Collaborate with subject matter experts to develop, update, test, and maintain learning content and employee communications.

• Organize the delivery of the mentorship program and manage the personal learning and development stipend.

• Monitor learning participation, completion rates, feedback, and ongoing support requirements to suggest enhancements.

• Maintain employee data, records, process documentation, and compliance evidence across shared systems.

• Implement compliance training processes, including Sexual Harassment Training, reminders, evidence retention, and support for security audits.

• Assist with documented People processes in Portugal and Prague, employee records, vendor coordination, and routine employee support during the initial transition phase.

• Develop workflows, checklists, templates, metrics, and escalation procedures to enhance accuracy, service quality, and business continuity.

⛳️ Requirements

• A minimum of 5 years of progressive experience in People Operations, HR Operations, or a similar role.

• Direct experience in supporting Canadian employees, along with familiarity with Canadian payroll, benefits, and employment administration.

• Proficient in using an HRIS and maintaining dependable employee records, workflows, and reports.

• 2-5 years of experience in administering a Learning Management System (LMS) or coordinating learning initiatives, including assignments, communications, tracking, and reporting.

• Background in managing learning and development, compliance training, mentorship, or other structured educational programs.

• Demonstrated ability to manage recurring, deadline-driven processes with high accuracy and confidentiality.

• Proven skills in project and program management.

• Excellent written and verbal communication skills.

• Strong judgment, dependable follow-through, and the ability to work comfortably in a remote, international, and dynamic environment.

• Competence in using AI assistants for drafting policies, optimizing workflows, and scaling impact.

• Hands-on experience with Rippling, 360Learning, JIRA, or similar HR, LMS, and service management platforms.

• Familiarity with instructional design, course maintenance, or learning content operations.

• Exposure to international People Operations, employer of record (EOR) arrangements, or post-acquisition integration.

• Experience supporting distributed teams across Canada, the United States, and Europe.

• Experience in healthcare, health technology, or another regulated industry is a plus.

🏝️ Benefits

• Target annual bonus.

• Comprehensive Canadian employee benefits.

• Personal learning and development stipend.

• Remote work arrangement.

• Flexible and autonomous work approach.