SUPERVISOR, SALES & RETENTION, INDIVIDUAL CHANNEL (HYBRID)

WHO WE ARE
When it comes to health, we’re always looking for ways to push for better. It’s why we were founded in the first place. In 1957, our founder, pharmacist William Wilkinson, witnessed a mother sacrifice her health by forgoing her own medicine to pay for her sick daughter’s prescription. He knew there had to be a better way. So, he introduced North America’s first prepaid drug plan, and GreenShield was born as a non-profit with a mission to support better health for all Canadians.

We aren’t just a health and benefits company. We’re the only non-profit social enterprise that brings worlds of coverage and care together, all in one place.
We’re noble challengers, purposefully building a better way and we need the best people to help us create a more holistic approach that takes care of the mind and body.

Our mission is to create better health for all Canadians, and we know that starts with our employees. 

THE ROLE IN A NUTSHELL

Base Salary:  CAD $74,269.00 - 92,837.00

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 environment 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'RE 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

THE CULTURE
We believe a career should be meaningful. Not just a means to earn a living. Our culture is one where everyone's voice is heard and valued. Because that’s what it takes to create better health for all. We dare to challenge the status quo. And we’re driven by people who have challenged theirs.  We believe that your workplace should empower you to be the best version of yourself. That’s why we provide a place where you can be inspired, challenged, and rewarded. 

Where your growth means our growth.
Where your voice is heard and valued.
Where your work has purpose. And purpose matters.

We believe our people are critical to our overall success. Inclusivity makes us a stronger, smarter and more informed organization. Being 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.

Here’s to Better Health for All!

A FEW MORE DETAILS
Proficiency in English is required for this position. As part of this role, you will be required to communicate with colleagues or customers who use English as their primary language.  By requiring English proficiency for this position, we aim to ensure that our employees can excel in their roles, collaborate, and communicate effectively, and contribute to the success of our organization. 

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.