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Johnston Group Inc.

Supervisor, Administration Services (Chambers Plan)

Winnipeg, MB, Canada

Job type: Full-time
Apply by: Oct 29, 2026
Posting language: English
Posted: Sep 29, 2026

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Original job description

Johnston Group provides employee benefit solutions to over 30,000 companies, ranging from one employee to thousands across various product lines, including Chambers of Commerce Group Insurance Plan, Canada’s #1 employee benefits plan for small businesses. JG is a platinum member of Canada’s Best Managed Companies and was named one of Manitoba’s Top Employers. We support a positive work atmosphere where we value the diversity in the people we serve and are looking for talent who will contribute to our diverse and inclusive workplace; where individual differences are recognized, appreciated, and respected. JG believes in giving back and contributes significantly to local health, arts, sports, and other community organizations.

As part of our Supervisor, Administration Services (Chambers Plan) team, you will work closely with the Manager of Administration Services to oversee the day-to-day operations of the Administration Services department, ensuring compliance with benefit plan guidelines, processes, and service standards. You will provide leadership and guidance to team members, support the resolution of complex administrative matters, manage advisor and internal inquiries, and review escalated cases while delivering exceptional service to internal and external stakeholders. This role carries a significant responsibility in supporting our Advisor network, acting as a key point of contact for daily inquiries, exception requests, and relationship management. As a Subject Matter Expert in Chambers Plan administrative guidelines and processes, you will provide expertise and guidance across the organization while contributing to the ongoing success of the department. You will also lead and participate in departmental and cross-functional projects and initiatives, representing Administration Services and helping drive operational excellence and continuous improvement.

In this role, you will support team development through training, coaching, quality assurance reviews, workload coordination, and cross-training initiatives. You will collaborate with Team Leads, Trainers, Human Resources, and other departments to drive operational excellence, improve processes, and support key business initiatives. Additionally, you will monitor team performance metrics, report results to leadership, oversee staffing and attendance management, contribute to renewal activities and risk assessments, and ensure timely communication of changes impacting Administration Services operations.

*Hybrid working model based out of our Winnipeg, MB office, with three days in-office per week.

Qualifications:

Excellent verbal and written communication skills, with the ability to clearly convey information, influence outcomes, and build strong working relationships with internal and external stakeholders
The ability to make quick decisions based on knowledge and experience
Aptitude for listening and responding to staff and client enquiries effectively and in a professional manner
Demonstrated ability to lead and support organizational change initiatives, including effectively communicating changes, engaging stakeholders, managing competing priorities, and helping teams adapt to evolving business needs
Strong organizational, time management, and problem-solving skills, with the ability to prioritize tasks, manage competing deadlines, and resolve issues effectively in a fast-paced environment
Ability to maintain confidentiality with sensitive and private information
Demonstrated ability to handle confidential and sensitive information with discretion and professionalism, while fostering an inclusive, respectful, and equitable team environment that values diverse perspectives and experiences
Previous leadership, supervisory, or team lead experience with a demonstrated ability to coach, develop, and support employees is a must

The successful candidate must be legally eligible to work in Canada. We thank all applicants for their interest. Please note that only those selected for an interview will be contacted.

JG welcomes the opportunity to provide accommodation throughout the selection process. Please contact us to discuss your requirements by email at human.resources@johnstongroup.ca or by phone at 204-788-7122.

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More about this job

Responsibilities

Oversee daily Administration Services operations, guide and develop team members, resolve complex administrative matters, and support advisors and internal stakeholders with inquiries and escalated cases. Lead departmental and cross-functional initiatives, monitor performance and staffing, contribute to renewals and risk assessments, and drive service quality and continuous improvement.

Requirements

Previous leadership, supervisory, or team lead experience, including the ability to coach, develop, and support employees, is required. Candidates should demonstrate strong communication, decision-making, organizational, problem-solving, change management, and confidentiality skills, and must be legally eligible to work in Canada.

Skills

Leadership
Coaching And Employee Development
Change Management
Communication
Problem-Solving
Decision-Making
Organization And Time Management
Prioritization
Confidentiality
Customer Service
Quality Assurance
Workload Coordination
Performance Monitoring
Process Improvement
Project Management

Visa sponsorship

Not detected in the job text

Keywords

Administration Services
Chambers Plan
Employee Benefits
Insurance
Benefit Plan Guidelines
Administrative Processes
Advisor Network
Stakeholder Management
Team Leadership
Coaching
Training
Quality Assurance
Workload Coordination
Cross-Training
Change Management
Performance Metrics
Staffing Management
Attendance Management
Renewal Activities
Risk Assessments
Project Management
Cross-Functional Collaboration
Operational Excellence
Continuous Improvement
Customer Service
Confidential Information

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