SUPERVISOR, SALES & RETENTION, INDIVIDUAL CHANNEL (HYBRID)

Role summary

SUPERVISOR, SALES & RETENTION, INDIVIDUAL CHANNEL (HYBRID) is a role at Green Shield Canada in Toronto, Ontario, Canada (hybrid). Posted 2026-08-09. Experience level: 5-10.

Job title

SUPERVISOR, SALES & RETENTION, INDIVIDUAL CHANNEL (HYBRID)

Company

Green Shield Canada

Location

Toronto, Ontario, Canada

Work arrangement

hybrid

Category

Sales

Experience level

5-10

Date posted

2026-08-09

Job description

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 requestforaccommodation@greenshield.ca. Information received relating to

accommodation will be addressed confidentially.

Providing this information gives

GS consent to use your personal information to a