Payroll and Benefits Lead - Fully Remote
Payroll and Benefits Lead - Fully Remote
Posted on :
26-07-2025
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1 Vacancy
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Job Description
Payroll and amp; Benefits Specialist
Fully Remote-first (GTA preferred)
$85K Stock Options 4 Weeks Vacation
Build 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 its 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 theyre looking for someone ready to take full ownership of the function.
This is more than just processing payroll. Its a chance to build smarter systems be the go-to expert across the company and partner directly with People and Finance leadership. If youre tired of maintaining outdated processes and want to leave things better than you found them - this is your role.
Youll 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
Youre someone whos:
- 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 Youll 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
- 35 years of payroll and/or benefits experience including cross-border (Canada and amp; 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
- $85000 base salary
- Stock option grant
- 4 weeks vacation paid holidays and wellness time
- $2000 home office setup budget (one-time)
- $500 annual professional development
- 4% RRSP match
- Comprehensive health and amp; 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 thats missing is the right person to own it.
Employment Type
Full Time
Key Skills
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