The Payroll Manager oversees strategic and operational leadership of payroll services across the United States, Puerto Rico, and Canada. The role ensures accurate, compliant, and timely payroll delivery, drives vendor and technology optimization, leads a high performing team, and partners with senior stakeholders to support transformation and continuous improvement initiatives.

Oversee and manage end to end payroll activities including audits, reconciliations, yearend processes, garnishments, benefits, equity, and special payments.

Ensure compliance with IRS, CRA, Puerto Rico Hacienda, and applicable state/provincial/local laws, as well as internal audit and SOX standards.

Lead the design, documentation, and testing of payroll controls and risk mitigation measures.

Maintain jurisdictional tax setup, updates, and adherence to legislative changes.

Maintain confidentiality and always safeguard sensitive payroll and employee data.

Lead and develop payroll specialists, and analysts; Provide coaching and in-depth technical expertise for all North American payroll jurisdictions.

Support workforce planning, hiring, and capability building aligned with future digital payroll needs.

Deliver and maintain payroll dashboards and KPIs (accuracy, timeliness, SLA performance, tax error rate, processing costs).

Provide reporting for Finance, Total Rewards, and Accounting (accruals, costing, headcount).

Communicate insights, risks, and opportunities to leadership.

Lead multi‑country payroll operations ensuring accuracy, timeliness, and regulatory compliance across all jurisdictions.

Develop and execute regional payroll strategies aligned with global policies and operating models.

Partner with senior HR, Finance, and Technology leaders to drive standardization and operational excellence.

Serve as the primary escalation point for complex payroll, taxation, and compliance issues.

Digital,



Data & AI Capability 20% Demonstrates robust functional expertise in enterprise payroll systems with the ability to understand end‑to‑end data flows, diagnose issues, and support system enhancements and integrations.

Leverages payroll data, dashboards, and AI‑enabled insights to perform reconciliations, analyze trends, identify risks, and support informed decision‑making.

Identifies and owns automation opportunities to reduce manual effort, improve accuracy, and strengthen controls, partnering effectively with IT and vendors.

Applies AI responsibly within payroll operations, using approved tools to enhance productivity while exercising judgment, validating outputs, and maintaining human oversight.

Ensures automation and AI‑supported processes comply with regulatory, data privacy, audit, and SOX requirements through strong governance and cross‑functional partnership.

Manage relationships with external payroll vendors (ADP, Deel etc.). and drive SLA performance and optimization.

Partner with HRIS/Workday teams to enhance integrations, improve data quality, and support configuration updates.

Influence payroll technology roadmaps, including automation, RPA, workflow tools, data insights, and digital transformation initiatives.

Lead issue resolution, root‑cause analysis, and implementation of long‑term corrective actions.

Collaborate with HR, Legal, Accounting, Total Rewards, and Time & Attendance teams on policy design and pay practices.

Support M&A; due diligence, onboarding, and payroll integrations.

Partner with global payroll leaders on shared services design, governance, and process harmonization.

2 Payroll Analysts and 1 Payroll and Benefit Administrator





Project management responsibilities

Has responsibility for leading project as it relates to payroll.

Minimum of 7 years of progressive payroll progressive payroll experience with significant U.Strong experience with Canadian payroll and Puerto Rico payroll.

Deep knowledge of payroll laws and compliance across North America.

Experience managing multi country payroll teams or leading a payroll function.

Proficiency with Workday and major payroll systems (ADP, Deel etc.).

Above average computer literacy, e.g., EXCEL, WORD, and various vendor applications.

Bachelors, CPP, FPC, PCP, or CPM certifications.

Experience with large scale payroll transformations, vendor consolidation, or digitalization initiatives.

If there is no posting end date listed then this is a pipeline requisition, and we will continue to collect applications on an ongoing basis.

Helping People Thrive in a Connected World Assurant is a leading global business services company that supports, protects, and connects major consumer purchases. A Fortune 500 company with a presence in 21 countries, Assurant supports the advancement of the connected world by partnering with the world’s leading brands to develop innovative solutions and deliver an enhanced customer experience through mobile device solutions, extended service contracts, vehicle protection services, renters insurance, lender-placed insurance products, and other specialty products.

Assurant supports the responsible use of Artificial Intelligence (AI), but we want to know the real you. Since we would like to know the real you, we require that all of our virtual interviews be conducted on video. Assurant is an Equal Employment Opportunity employer and does not use or consider race, color, religion, sex, national origin, age, disability, veteran status, sexual orientation, gender identity, or any other characteristic protected by federal, state, or local law in employment decisions. #

📌 Payroll Supervisor - Operations (Winnipeg)
🏢 Assurant
📍 Winnipeg