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About the Role

As the Supervisor, Sales & Retention, you will lead a team of 10–12 Licensed Insurance Advisors in a high-performance contact centre environment. You are accountable for driving sales outcomes, elevating advisor capability through coaching, and ensuring operational excellence, all while reinforcing GreenShield’s social mission and customer-first mindset.

Responsibilities

• Drive team sales performance across all lead types
• Monitor KPIs (conversion, call quality, adherence etc.) and take immediate action to close gaps
• Build a high-performance culture with clear expectations and accountability
• Delivery of structured, ongoing sales coaching (call reviews, side-by-sides, etc.)
• Identify individual skill gaps and implement targeted development plans by working closely with our Health & Dental Specialist
• Reinforce best practices in needs-based selling, objection handling, and compliance etc.
• Oversee day-to-day operations of a phone-based sales team (scheduling, queue management, productivity)
• Ensure adherence to service levels, QA standards, and regulatory requirements
• Partner with QA, Training, and Workforce Management to optimize performance
• Ensure advisor licensing is kept up to date and complaint
• Work with new advisors to ensure all their sales are reviewed and meet compliance requirements
• Actively leverage CRM, QA platforms, and reporting tools to drive insights and productivity
• Stay current with and champion emerging technologies (AI-assisted coaching, automation, digital sales tools)
• Use data to inform decisions and continuously improve team outcomes
• Build an engaged, inclusive team environment with strong retention and morale
• Lead performance management, recognition, and career progression for advisors
• Model professionalism, resilience, and strong communication
• Act as the first point of leadership support for all customer and advisor escalations to ensure escalations are handled consistently and within regulatory standards
• Resolve complex client situations with a customer-first, retention-focused approach
• Champion GreenShield’s social mission in daily leadership and decision-making
• Ensure advisors connect product value to improving Canadians’ health and well-being

Requirements

• 5 years sales coaching experience in a contact centre environment, with experience managing the day-to-day operations of a phone-based team
• Licensed across multiple Canadian provinces (not including QC)
• Strong working knowledge of contact centre technologies
• Proficiency in English is required for this position
• Ability to communicate with colleagues or customers who use English as their primary language

Skills

• Sales coaching
• Contact centre operations management
• Needs-based selling
• Objection handling
• Compliance
• CRM
• QA platforms
• Reporting tools
• AI-assisted coaching
• Automation
• Digital sales tools
• Performance management
• Leadership
• Communication
• Escalation management

Location

• Canada

Work Type

• Contact Centre
• Phone-based

Experience Level

• Supervisor
• 5 years sales coaching experience

Education Level

• College Diploma/University Degree
• LLQP/HLLQP certification

Salary/Compensations

• CAD $74,269.00 - 92,837.00

Benefits

• Health & Dental experience is preferred

About the Company

• GreenShield is a non-profit social enterprise that brings worlds of coverage and care together.
• Founded in 1957, GreenShield introduced North America’s first prepaid drug plan.
• Mission: to support better health for all Canadians.
• Noble challengers, purposefully building a better way.
• Culture: career should be meaningful, everyone's voice is heard and valued, dare to challenge the status quo, workplace should empower you to be the best version of yourself, inspired, challenged, and rewarded.
• Inclusivity makes us a stronger, smarter and more informed organization.
• Intentionally inclusive of diverse backgrounds, perspectives and experiences will enhance our company culture to positively impact how we support our communities.
• A career at GreenShield isn’t just about personal achievements, it's about making a difference together.

Equal Opportunity

• GS supports diversity, equity and inclusion in our teams and communities, and we value the unique contributions made by all.
• Even if your experience doesn’t align perfectly to every requirement, we invite you to apply.
• We encourage applications from all candidates and will accommodate needs under human rights legislation throughout all stages of the recruitment and selection process.
• Please let us know of any accommodation through requestforaccommodation@greenshield.ca. Information received relating to accommodation will be addressed confidentially.