THE ROLE IN A NUTSHELL

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.

Key Responsibilities

Sales Leadership & Performance

- 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

Coaching & Development
- 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.

Contact Centre Operations
- 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

Technology & Innovation
- 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

People Leadership
- Build an engaged, inclusive team workplace with strong retention and morale
- Lead performance management, recognition, and career progression for advisors
- Model professionalism, resilience, and strong communication





Escalation Management
- 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

Mission Alignment
- Champion GreenShield’s social mission in daily leadership and decision-making
- Ensure advisors connect product value to improving Canadians’ health and well-being

WHO WE ARE LOOKING FOR

- Education - College Diploma/University Degree
- Cert/Designations – LLQP/HLLQP
- 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
- Health & Dental experience is preferred

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 [email protected]. Information received relating to accommodation will be addressed confidentially. Providing this information gives GS consent to use your personal information to assess your suitability for specific positions, future opportunities or for your personnel file. Your résumé will be held in strict confidence and will be viewed only by the Organization. Information may be stored outside of Canada and could be used for aggregate statistical purposes (which uses no personal identification).

AI Usage - GreenShield leverages AI to help produce Job Descriptions, and ideate on interview questions. We also leverage AI for interview transcription support.

📌 SUPERVISOR, SALES & RETENTION, INDIVIDUAL CHANNEL (HYBRID) (Toronto)
🏢 GreenShield
📍 Toronto