People Operations Specialist, Too Good To Go

• We’re looking for a highly organized and execution-driven People Operations Specialist to be based in our Toronto office
• This role is ideal for someone who enjoys balancing structure with adaptability — owning payroll, benefits, employee support, and HR administration while helping improve and scale our People Operations function across Canada and the US
• Success in this role requires strong attention to detail, sound judgment, a proactive mindset, and the ability to navigate a fast-paced environment with confidence and care
• 2+ years of experience in Human Resources or People Operations within a fast-paced environment
• Hands-on experience with HR operations, payroll, and benefits in both Canada and the US. (Note: Experience in both regions is a strict requirement.)
• Strong understanding of HR processes, policies, and compliance considerations across North America
• You have a high-ownership mindset and thrive in an execution-focused environment. Whether managing tasks independently or working across internal teams and external vendors, you move work forward with urgency and consistently “get it done”
• You communicate confidently across teams, navigate ambiguity, and independently drive initiatives forward without needing close direction
• You have strong organizational skills and can seamlessly manage competing priorities with consistent follow-through
• You have strong written and verbal communication skills and can confidently work across all levels of the organization
• You handle highly sensitive employee information with absolute discretion and sound judgment
• You’ll thrive here if you have a sharp memory and impeccable attention to detail
• You are someone who truly loves checking off boxes and excels at running the day-to-day processes that keep a company moving
• At the same time, this role requires flexibility and sound judgment
• When edge cases arise, you’re comfortable pausing routine work to focus on what’s most urgent, investigating issues directly or escalating them appropriately

Desirable

• You’ll play a key role in delivering a seamless employee experience, supporting managers and employees, and ensuring operational excellence across our systems and processes
• Employee Support:
• Provide first-level support on employee relations matters, including policy interpretation, issue resolution, and escalation, as needed
• Partner closely with our Workplace Experience Manager to ensure a smooth and well-coordinated employee lifecycle experience
• Serve as a resource for managers on performance matters and employee relations, ensuring alignment with our internal policies and values
• Payroll and Benefits:
• Own payroll processing and validation for Canada and the US, ensuring all standard pay, timecards, and ad-hoc adjustments (e.g., new hires, terminations, bonuses) are accurate
• Manage year-end payroll activities, focusing on hands-on T4 preparation and reconciliation for Canada while ensuring our US PEO successfully issues W-2s
• Administer employee benefits programs, including enrollments, changes, terminations, and responding to employee inquiries
• Ensure payroll practices comply with federal, provincial/state, and local regulations, including remittances, filings, and record retention
• HR Systems and Administration:
• Drive high-volume delivery of core HR lifecycle processes, maintaining precision and speed across onboarding, offboarding, and leave administration
• Maintain accurate employee data and records across our HR tech stack (e.g., HiBob, Justworks, Payworks)
• Support ongoing HR file and documentation management, ensuring consistency and accuracy across systems

• Please submit your resume and cover letter in English. A member of our team will be in touch within a few weeks. We look forward to reading your application!