Customer Success Manager – Ontario: Field Position

Insurance Insight Inc.; Toronto; Hybrid; CAD 65,000 - 95,000; Full time

Benefits offered by this job

Health insurance

Dental insurance

Life insurance

Disability

Group retirement savings

Three weeks vacation

Job summary

Insurance Insight Inc. in Ontario is seeking a Customer Success Manager to support our retailer network across Ontario and beyond. This field position focuses on training and activation to shorten the time from retailer sign-up to active production.

You will deliver in-person and virtual training, lead the training side of retailer launches, and collaborate with the Business Development Manager to re-engage inactive retailers. Travel is heavy, with 30%+ field time and overnight stays.

Qualifications

• Post-secondary education in Business, Marketing, or Adult Education.
• Automotive retail experience required; comfortable with field work.
• Experience delivering training to adult audiences, in-person and virtual.
• Excellent presentation, communication, and organizational skills.

Responsibilities

• Plan and deliver high-quality training to retailer partners in person and virtually.
• Lead training for new retailer launches and relaunch training as needed.
• Coordinate field visits and manage calendars across regions.
• Develop and maintain training materials and retailer communications.
• Track engagement and reactivation progress with management.

Skills

Training delivery

Public speaking

Presentation skills

Coaching

Organization

Communication

Field work

LMS familiarity

Education

Business/Marketing/Adult Education degree

Tools

Learning management systems

Video conferencing

Presentation tools

Job description

Customer Success Manager - Ontario: Field Position

Insurance Insight Inc. (formerly WALKAWAY® Canada Inc.) pioneered creditor insurance 25 years ago. We are an insurance brokerage specializing in providing automotive manufacturers and dealerships in North America and around the world with high-quality insurance-based products and technology solutions. We specialize in large national automobile after-market products, such as creditors insurance and GAP insurance, enabling a minimum amount of administration with the maximum amount of return.

We are currently recruiting for a Customer Success Manager, a newly created field position supporting our retailer network across Ontario and beyond. The ideal candidate would be based in the Greater Toronto Area.

As the Customer Success Manager, you are the training and activation specialist for our retailer partners. You are responsible for delivering high-quality, consistent training that shortens the time from retailer sign-up to active production and supports sustained performance thereafter. Working alongside the Business Development Manager responsible for each account, you will lead the training side of new retailer launches, deliver in-person and virtual training, and work to re-engage retailers who have become inactive. This is an active, field-focused role where strong planning, organization and follow-through are required for success.

Responsibilities:

Plan and deliver high-quality, consistent training to retailer partners in person, in groups and one-on-one, covering sales and F&I Manager development, product knowledge and positioning, and OEM and lender partner programs.

Deliver engaging virtual training, including national and retailer webinars, and lead recurring programs such as WALKAWAY Wednesdays.

Lead the training side of new retailer launches, and deliver relaunch training for retailers experiencing changes in programs, engagement or personnel.

Manage an assigned portfolio of inactive retailers with the responsible Business Development Manager; identify reasons for disengagement and recommend a path to renewed production.

Spend time in retailer locations to gather feedback and provide field insight that shapes the national Customer Success program.

Develop and maintain training materials, presentations and retailer-facing communications, including Market Pulse.

Deliver internal training and product briefings to other departments, and support Business Development with train-the-trainer sessions as the role develops.

Plan and manage a full calendar of retailer training and field visits, coordinating with the National Customer Success Manager and Business Development Managers; use available tools to track engagement and reactivation progress.

Maintain expertise across company and partner programs, and ensure training is delivered in accordance with relevant regulatory requirements.

Qualifications and Skills:

Post-secondary education in Business, Marketing, Adult Education or a related field preferred.

Automotive retail experience (F&I, Sales Manager, GSM, GM or Training Specialist) required; comfortable inside dealerships and working with a field sales team.

Experience delivering training, facilitation or sales coaching to adult audiences, both in-person and virtually, to groups and individuals.

Engaging, confident presenter who communicates clearly and handles questions and objections well, including with large groups and senior audiences; builds polished, professional materials and clear retailer-facing communications.

Highly organized and process-focused; able to manage their own calendar, logistics and reporting autonomously across multiple retailers, regions and programs.

Able to coach and influence without direct authority, integrating well into an experienced field team as a shared resource.

Comfortable with learning management systems, video conferencing and presentation tools; AI-assisted content or video editing skills an asset.

Being a Registered Insurance Brokers of Ontario (RIBO) Level 1 licence holder, or obtaining the licence within six months of hire is a condition of employment; paid study time provided.

Valid Driver’s Licence and a reliable vehicle.

30%+ of working time in the field, including overnight stays and travel outside Ontario; training is scheduled around retailer availability, with early starts, evenings and occasional weekends.

Must be authorized to work in Canada; offer conditional on a satisfactory background check.

Benefits and Perks:

We provide a competitive compensation and benefits program, including health, dental, life insurance, disability, group retirement savings, and three weeks of vacation to start. We will provide you with all the necessary tools you’ll need to be effective in your new role.

We are looking for people who share our values, first and foremost, to join our team. We believe our team members represent our single biggest investment and our most valuable asset. We know that in today’s highly competitive job market, talented people can work anywhere. Our values and culture are sacred; they define and differentiate us from other employers. We are proud to be named as one of Canada’s Most Admired™ Corporate Cultures and a Top Insurance Workplace.

Insurance Insight welcomes applications from people with disabilities. Accommodations are available on request for candidates participating in any aspect of the application, assessment and selection process.