Supervisor, New Business Implementation

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.

The Supervisor, New Business Implementation, plays an important leadership role within our Administration Team by providing daily guidance, support, and direction to a team of Benefit Implementation and Maintenance Administrators. This position is responsible for creating a productive and collaborative environment where team members feel supported and equipped to deliver accurate, timely, and high‑quality service to our clients.

In this role, you will oversee the flow of work coming into the team, ensure workloads are balanced, and monitor service and quality expectations. You will act as a resource for escalations and complex issues by offering sound judgment and clear decision making. The Supervisor helps drive continuous improvement by identifying opportunities to streamline processes, encouraging knowledge sharing, and supporting training needs across the team.

You will work closely with internal partners such as Sales, Underwriting, Claims, and the QA and Training team to support new business activities and ensure we deliver a positive customer experience. You will also support the manager in performance management and contribute to building a team culture that values communication, collaboration, learning, and operational excellence.

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

• Support and mentor the team in their day‑to‑day responsibilities, offering guidance and problem‑solving support.
• Assist the manager with performance management for direct reports.
• Monitor and maintain customer service and quality standards.
• Review, prioritize, and manage workloads to ensure efficiency and service consistency.
• Support the handling and resolution of escalations and complex inquiries.
• Work with the team to identify opportunities to improve and streamline processes.
• Partner with the QA/Training team to identify training gaps and support development.
• Maintain strong relationships with insurance carrier partners and communicate guideline updates to the team.
• Contribute to the new business sales process by supporting effective collaboration with Sales, Underwriting, and Claims.

• 2–5 years of experience in insurance or group benefits.
• Demonstrated leadership abilities with experience supporting or guiding others.
• Strong interpersonal and written communication skills.
• Solid understanding of group benefits administration and related processes.
• Strong problem‑solving and conflict‑resolution abilities.
• Adaptable, flexible, and comfortable with changing priorities.
• Ability to manage multiple competing priorities.
• Ability to work collaboratively and support a team through change.
• Commitment to continuous learning and development.
• Strong analytical and critical‑thinking skills.
• Demonstrated coaching and mentoring capabilities.
• Proficient in Microsoft Office.
• Industry education such as CEBS, LOMA, or HIAA is considered an asset.

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 huma or by phone at .