Payroll & Benefits Lead
AuditFriendly Careers • Remote • Full Time • $85,000–$85,000 / year
Posted on Mon, Oct 5, 2026
Payroll & Benefits Specialist
Fully Remote-first (GTA preferred)$85K + Stock Options + 4 Weeks VacationBuild It. Own It. Elevate It.
Our client is building the future of retail media networks, helping retailers turn digital marketing into a profit center. Backed by cutting-edge AI and automation, their platform delivers performance that outpaces online media benchmarks and it’s already trusted by some of the biggest names in retail.Headquartered in Toronto and operating remotely, they are a diverse, high-performance team of professionals who care deeply about building meaningful products, driving results, and shaping a positive, inclusive culture.They are now bringing payroll and benefits in-house for the first time and they’re looking for someone ready to take full ownership of the function.
This is more than just processing payroll. It’s a chance to build smarter systems, be the go-to expert across the company, and partner directly with People and Finance leadership. If you’re tired of maintaining outdated processes and want to leave things better than you found them - this is your role.
You'll step into a high-impact position with immediate visibility, autonomy, and the runway to modernize how payroll and benefits are delivered across Canada, the U.S., and beyond.
Why This Role Stands Out
- Greenfield opportunity - Take over from an outsourced provider and make it your own
- High-trust, low-bureaucracy environment
- System migration in motion - Play a leading role in selecting and implementing a global payroll provider
- Full leadership support - Reporting to the Head of People, with close collaboration from the CFO, Controller, and Director of Finance
Ideal Candidate Profile
You're someone who’s:- Ready to step out of a narrow, task-based payroll role
- Looking to own and shape a function from the ground up
- Energized by tech, systems, and solving messy problems
- Trusted, accountable, and happiest when people rely on you
What You'll Do
- Own end-to-end Canadian and U.S. payroll (plus one employee in Australia)
- Lead benefits administration and employee onboarding conversations
- Serve as the first point of contact for all payroll and benefits inquiries
- Drive a payroll system migration (vendors like ADP currently being evaluated)
- Improve documentation, workflows, and compliance processes
- Support broader compensation projects and people operations initiatives
What Our Client Is Looking For
- 3–5 years of payroll and/or benefits experience, including cross-border (Canada & U.S.)
- Experience with platforms like Humi, Gusto, Paychex, Rippling, or HiBob
- Strong attention to detail and comfort working autonomously in a remote setting
- Knowledge of Canadian and U.S. employment standards, tax regs, and compliance
- Proactive communicator with strong interpersonal and problem-solving skills
- CPA, PCP, CPM, or related certification is a plus
- Familiarity with multi-entity, multi-currency, and PEO/EOR environments is an asset
Total Rewards
- $85,000 base salary
- Stock option grant
- 4 weeks vacation + paid holidays and wellness time
- $2,000 home office setup budget (one-time)
- $500 annual professional development
- 4% RRSP match
- Comprehensive health & dental benefits
- Monthly virtual DoorDash team lunches
- Enhanced parental leave coverage
- Annual performance review and salary increase cycle
Why Now?
This is a rare opportunity to build something meaningful at exactly the right time. The strategy is set. The team is supportive. The migration is coming. All that’s missing is the right person to own it.More live payroll_specialist roles
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