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Payroll and Benefits Leader

Confidential

Winnipeg, Manitoba permanent

Posted: January 30, 2026

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Quick Summary

The Payroll & Benefits Leader will oversee payroll and benefits administration, ensuring accurate and timely processing, and implementing best practices, liaising with internal departments, and streamlining processes.

Job Description

Enter the Game!

Activate is a tech company known for creating Canada’s first full-scale interactive gaming facility. The Payroll & Benefits Leader will be responsible for overseeing payroll and benefits administration and leading a team of specialists.  Reporting to the Director of Finance, the Payroll & Benefits Leader will ensure accurate and timely payroll processing, benefits administration and reporting for Activate’s Canadian and US Operations.  This role will also play a key role in streamlining processes, implementing best practices, liaising with internal departments, and ensuring proper compliance with applicable payroll & benefits laws.  This is a hands-on role - ideal for a leader who thrives on execution and collaboration.  

The Duties and Responsibilities:

Leadership 

Lead the payroll team and oversee the daily workflow of the function, ensuring effective delivery of services

Oversee the quality of all deliverables from the team, ensuring excellence in execution

Manage performance and staff by providing ongoing coaching and feedback; tracking training and evaluations of employees 

Collaborate with HR and Finance to align benefits, compensation, and reporting

Payroll Processing and Compliance

Ensure compliance with federal, provincial/state, and local payroll regulations; provide guidance by staying informed on Canadian and U.S legislative updates, tax regulations, payroll compliance requirements, and emerging industry practices 

Register with federal, provincial/state, and local payroll authorities

Oversee payroll audits and resolve discrepancies

Ensure proper communication and retention of technical and confidential payroll information

Responsible for approval of end-to-end payroll processing for all employees

Collaborate with payroll and HR software providers to build efficiencies in payroll processing

Establish proper setup of payroll software to accurately process payroll

Lead the development of payroll procedures, internal controls, and audit processes to ensure accuracy and compliance

Prepare and distribute payroll reporting for management

Perform other related duties as assigned

Benefits Administration

 

Lead the administration of benefits programs and compliance reporting in accordance with legal standards

Oversee the processing of group benefits enrollments, amendments, terminations, and responses to employee questions

Stay informed of regulatory changes affecting benefits plans and ensure practices meet regulatory requirements

Develop, maintain, and train standard operating procedures for benefits administration

The Qualifications:

Post-secondary education in accounting, business, or human resources is required

PCP/PLP/CPP designation is required

5+ years of experience in payroll administration with 3 + years of supervisory/leadership experience

2+ years of experience in benefits administration in Canada and the USA

Proven working knowledge of payroll practices in Canada and the USA

Strong knowledge of payroll systems; ADP experience is a strong asset

The Perks:

Competitive Salary

Benefits package

Paid time off

Casual dress 

Employee discount

On-site parking

 

About Activate:

Taking entertainment into the future by fusing technology and physical activity together to create live-action gaming experiences, Activate is a technology company building interactive gaming facilities with locations across Canada and the US.  For more information about Activate, please visit http://playactivate.com/ or check us out on Instagram - @activategames/Facebook @activategames.

Activate is an equal opportunity employer. All qualified applicants will receive consideration for employment. Activate is committed to providing access, equal opportunity and reasonable accommodation for individuals with disabilities in employment, its services, programs and activities. To request reasonable accommodation for a protected characteristic, contact [email protected] which is an email monitored for this purpose.

We thank all applicants for their interest, however, only those candidates selected for interviews will be contacted.

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