ABOUT APPLYAPPLY 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. APPLY is hybrid remote daily. THE ROLEAs 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. 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. 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 advantages-related expenses. 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 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. 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. using Claude) that streamline payroll, benefits, and HRIS processes, reduce manual effort, and improve data accuracy. 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. 7+ years of progressive experience in Payroll and People Operations, with at least 3+ years at a lead level within a quick-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. 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. Fluent in Spanish an asset. Familiarity with employer of record models and tools like Deel, Remote, or Oyster.

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. Broaden your skills on a range of engagements with international brands that have a global impact. We’re truly committed to building a culture where you are celebrated and everyone feels welcome and safe.

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); 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 secure, respectful, and inclusive community where differences are celebrated. Learn more in our Diversity, Equity, and Inclusion (DEI) section.

📌 Payroll & Rewards Operations Lead (Winnipeg)
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📍 Winnipeg