Senior Manager Payroll

Lands' End•Dodgeville, WI

About The Position

The Senior Payroll Manager leads the end-to-end bi-weekly payroll function for a large, multi-state retail organization with a diverse employee population (4000+) including corporate, distribution center, and store teams. This role is responsible for ensuring accurate, compliant, and timely payroll processing; optimizing payroll systems and operations; managing payroll governance; and leading a team of payroll professionals. Facilitates setup, troubleshooting and maintenance of Time and Attendance system. The ideal candidate brings deep payroll expertise, extensive knowledge of UKG Pro, strong leadership skills, and experience operating in a fast-paced retail environment with high-volume transactions. Payroll Operations & Compliance Oversee full-cycle, multi-state payroll processing for hourly and exempt employees across retail stores, distribution centers, and corporate functions. Ensure payroll is processed accurately, on schedule, and in compliance with federal, state, and local regulations, including wage & hour laws, garnishments, taxes, and reporting requirements. Partner with Finance and Accounting on payroll-related journal entries, reconciliations, and labor reporting. Partners with HR and Benefits regarding time off/leave, benefit deduction configuration & 401k plan. Systems administrator for UKG Time and Attendance application. Responsible for making all changes and testing before rollout. Monitor changes in tax and labor legislation, ensuring timely system and process updates to maintain compliance. Serves as primary contact for payroll for internal and external audit activities. Oversee year-end payroll processes, including W-2 distribution, taxable benefit reporting, and regulatory filings. Leadership & Team Management Lead, develop, and coach a team of payroll specialists and analysts, promoting a culture of accuracy, accountability, and continuous learning. Establish performance goals, conduct reviews, and provide ongoing training in payroll best practices. Collaborate cross-functionally with HR, Benefits, IT, Finance, and Operations to ensure aligned and efficient service delivery. Systems & Process Optimization Own payroll system governance; partner with HRIS and IT on configuration, upgrades, testing, and integrations (e.g., timekeeping, HRIS, benefits systems). Drive process improvements to increase accuracy, enhance data flow, improve cycle times, and reduce risk. Ensure strong internal controls are in place to support auditing, compliance, and financial integrity. Lead payroll-related projects, including system implementations, vendor transitions, and automation initiatives. Customer Service & Employee Experience Oversee resolution of complex payroll questions escalated from HR or field operations. Maintain service-oriented practices that deliver clear and responsive communication to employees and leaders. Proactively identify trends or recurring issues and recommend solutions.

Requirements

Bachelor’s degree in Accounting, Business or relevant field or equivalent experience
8-12 years of experience, with a proven leadership capabilities.
Expertise in multi-state, high-volume payroll for a large, decentralized workforce.
Strong knowledge of federal and state payroll regulations, tax laws, wage & hour rules, and reporting standards.
Experience with enterprise HRIS/payroll systems (e.g., UKG, Workday, SAP Success Factors)
High attention to detail with strong analytical and problem-solving skills.

Nice To Haves

Advanced degree (e.g., MBA) preferred
CPP (Certified Payroll Professional) or FPC certification.
Experience in a publicly traded, multi-site retail organization.
Experience with SOX compliance and internal audit processes.

Responsibilities

Oversee full-cycle, multi-state payroll processing for hourly and exempt employees across retail stores, distribution centers, and corporate functions.
Ensure payroll is processed accurately, on schedule, and in compliance with federal, state, and local regulations, including wage & hour laws, garnishments, taxes, and reporting requirements.
Partner with Finance and Accounting on payroll-related journal entries, reconciliations, and labor reporting.
Partners with HR and Benefits regarding time off/leave, benefit deduction configuration & 401k plan.
Systems administrator for UKG Time and Attendance application.
Responsible for making all changes and testing before rollout.
Monitor changes in tax and labor legislation, ensuring timely system and process updates to maintain compliance.
Serves as primary contact for payroll for internal and external audit activities.
Oversee year-end payroll processes, including W-2 distribution, taxable benefit reporting, and regulatory filings.
Lead, develop, and coach a team of payroll specialists and analysts, promoting a culture of accuracy, accountability, and continuous learning.
Establish performance goals, conduct reviews, and provide ongoing training in payroll best practices.
Collaborate cross-functionally with HR, Benefits, IT, Finance, and Operations to ensure aligned and efficient service delivery.
Own payroll system governance; partner with HRIS and IT on configuration, upgrades, testing, and integrations (e.g., timekeeping, HRIS, benefits systems).
Drive process improvements to increase accuracy, enhance data flow, improve cycle times, and reduce risk.
Ensure strong internal controls are in place to support auditing, compliance, and financial integrity.
Lead payroll-related projects, including system implementations, vendor transitions, and automation initiatives.
Oversee resolution of complex payroll questions escalated from HR or field operations.
Maintain service-oriented practices that deliver clear and responsive communication to employees and leaders.
Proactively identify trends or recurring issues and recommend solutions.
Oversees multiple teams or a larger functional area.
Develops and executes strategies to meet business objectives.
Builds strong cross-functional relationships.
Drives team performance and professional development.
Lead and manage a team of employees.
Provide guidance, support, and mentorship to team members.
Foster a collaborative and positive work environment.
Set performance expectations and goals for team members.
Conduct regular performance evaluations and provide constructive feedback.
Identify and address performance issues through coaching and disciplinary actions when necessary.
Participate and recruitment and onboarding of new team members, as needed.
Identify training needs within the team and coordinate relevant development programs, encourage continuous learning and skill development among team members.
Serve as liaison between upper management and team, conveying organizational goals and expectations.
Address conflicts or issues within the team promptly and effectively.
Manage team resources, including workload distribution and project assignments.
Ensure optimal utilization of team member’s skills and expertise.
Collaborate with upper management to establish team goals aligned with organizational objectives.
Contribute to the development and implementation of department strategies.