Payroll & Rewards Operations Lead

ABOUT APPLY

APPLY is the Agentic Customer Experience (ACx) partner for the world's most ambitious consumer and entertainment brands. We bring together deep domain expertise across Retail, CPG, Sports, and Media with AI-native delivery capability, designing and delivering agentic solutions that turn CX vision into commercial reality. We are the partner of choice for brands like Arc'teryx, NFL, Lululemon, and Kraft Heinz. For more information, visit applydigital.com.

Location: APPLY is hybrid remote daily. The preferred candidate should be based in the Greater Toronto area of Canada, working hours that align to ET.

THE ROLE

As a Payroll & Rewards Operations Lead, you’ll be a cornerstone of our global People Operations function, sitting at the intersection of global rewards and people analytics. You will drive the processes around payroll, benefits, HR system administration and support the programs that keep our People function running accurately and at scale. This is a high-ownership, detail-driven role for someone who thrives on compliant execution, data integrity, process optimization, and delivering a seamless experience across the entire employee lifecycle in a fast-growing, global organization.

RESPONSIBILITIES

Payroll Execution

• Oversee day-to-day payroll administration and processing, acting as an advisor to People & Culture Leads for life cycle events with complex payroll implications.
• Take full accountability for overall payroll compliance and accuracy, validating all inputs and outputs across Canada, USA, UK, Chile, and EoR ahead of each cycle.
• Provide backup payroll processing coverage to ensure uninterrupted, on-time payroll.
• Monitor and improve data quality and speed when generating new employee profiles to seamlessly trigger the HRIS onboarding processes.
• Partner with Finance to perform monthly general ledger reconciliations and ensure accurate accruals and cost forecasting for payroll and benefits-related expenses.
• Collaborate on month-end close reporting, providing variance analysis and resolving discrepancies.

Total Rewards & Benefits

• Serve as a subject matter expert across the global benefits programs (Canada, USA, UK, EoR), interfacing with benefits brokers, managing renewal dates, producing regular reporting and executing reconciliation processes.
• Manage employee health benefits and retirement plan administration.
• Collaborate with the People & Culture Director to evaluate benefit plan composition, utilization and renewal strategies.
• Own total rewards communication and employee education programs that drive awareness and engagement.
• Serve as the tier-2 escalation point for employee inquiry cases, resolving complex or sensitive issues.
• Collaborate with People & Culture Leads to initiate, manage, and track leave of absences, aligned to global policy and compliance requirements.
• Support recurring pay equity analysis in partnership with the People Operations Lead.

HRIS & Systems Administration

• Manage the day-to-day relationship with Deel, holding the vendor accountable for product enhancements and support levels.
• Monitor day-to-day HiBob and Deel administration performed by People Operations Specialists, including regular data quality audits and ongoing system integrity monitoring.
• Design and build HiBob and Deel workflow enhancements, administer complex edge-case scenarios, and leverage system data to deliver actionable Business Insights to leadership.
• Support audit readiness and respond to internal and external audit requests with accurate, timely documentation.
• Partner with People Operations and cross-functional teams to identify, design and implement AI-enabled automations (e.g., using Claude) that streamline payroll, benefits, and HRIS processes, reduce manual effort, and improve data accuracy.

Analytics & Insights

• Own the development and tracking of key People & Culture metrics, creating dashboards and data models that translate raw HRIS data into strategic analytics and insights for the global team.

REQUIREMENTS

• 7+ years of progressive experience in Payroll and People Operations, with at least 3+ years at a lead level within a fast-growing, global organization.
• Experience with Canada and USA payroll (UK and Chilean experience an asset).
• Proven track record of managing and supporting finance and payroll audits, ensuring accurate general ledger reconciliations and full audit readiness.
• Proven experience administering payroll and total rewards across the employee lifecycle for a global employee base (compliance, benefits, and leave management).
• High-ownership mentality with the ability to evaluate business opportunities and risks to make sound decisions independently and communicate to stakeholders.
• Expert-level administration experience with HiBob (strongly preferred) or a comparable modern global HRIS (e.g., Workday, Rippling, BambooHR), including building complex workflows and automations.
• Advanced proficiency with spreadsheets (VLOOKUPs, Pivot Tables, Index/Match) with experience translating raw HR data into dashboards and executive insights (Google Sheets preferred).
• Experience managing sensitive payroll escalations or complex leave/benefits cases with empathy and discretion.
• Compliance and audit mindset, with a strong attention to detail to identify anomalies and investigate root cause ahead of audit cycles.
• Fluent in Spanish an asset.

Nice to Have

• Experience working in a global People & Culture team, supporting workers across many countries.
• Familiarity with employer of record models and tools like Deel, Remote, or Oyster.
• Exposure to DEI, wellness, or internal communication initiatives.
• Hands-on experience using generative AI tools (such as Claude) to build or improve workflows, reporting, or process documentation.

$105,000 - $125,000 a year

The salary range for this role is $105,000 - $125,000. We conduct regular benchmarking across various roles, similar industries, and levels to ensure fair compensation packages for all. We are committed to acknowledging each individual's unique strengths and contributions while rewarding the value that they deliver to the team.

LIFE AT APPLY

People are at the core of everything we do at APPLY. We provide you with modern tools, systems and approaches, value your time, safety, and health, and strive to build a work community where you can thrive and grow. Here are a few benefits we offer to support you:

• Agentic Delivery: Our people work in a modern way to deliver client outcomes. Broaden your skills on a range of engagements with international brands that have a global impact.
• An inclusive and safe environment: We’re truly committed to building a culture where you are celebrated and everyone feels welcome and safe.
• AI & Strategic Upskilling: Accelerate your professional growth with generous training budgets and mentorship, with a specific focus on Agentic AI expertise and the critical human skills required for the future of work.
• Generous vacation policy: Work-life balance is key to our team’s success, so we offer flexible personal time off (PTO); allowing ample time away from work to promote overall well-being.
• Customizable benefits: Tailor your extended health and dental plan to your needs, priorities and preferences.
• Flexible work arrangements: We work in a variety of ways, from remote, to in-office, to a blend of both.

APPLY is a safe, respectful, and inclusive community where differences are celebrated. We are committed to equal opportunity and fostering a workplace where everyone belongs. Learn more in our Diversity, Equity, and Inclusion (DEI) section. For recruitment accommodations, please email View email address on apply.j-vers.com.