Dealer Development Representative – Winnipeg Area, Manitoba

At Your Warranty Team (YWT) Dealer Services, we’re building something different. We partner with automotive dealerships as trusted advisors, not transactional salespeople - and we’re looking for professionals who take pride in doing the same. This role is for someone who values relationships as much as results, thrives with autonomy, and wants to be part of a high-performance culture.

If you’re driven to represent a brand that genuinely cares about its partners, this is where you belong. Who We Are – YWT Dealer Services – Built on What’s Right YWT Dealer Services is one of Canada’s fastest-growing provider of automotive protection products, built on doing right by dealers and customers every step of the way. We partner with dealers as trusted advisors - delivering programs, technology, and hands‑on support that change how protection is perceived and experienced.

The Role We’re looking for a Dealer Development Representative based in the Winnipeg Area, Manitoba to grow and manage dealer partnerships. This is a field‑based role for someone who thrives on autonomy, relationship‑building, and driving real business results. Compensation and Benefits This role is designed for high performers who want autonomy, uncapped earnings, and the ability to drive their own success. $90,000 base salary + Commissions Uncapped earning potential Comprehensive benefits package, including health, dental, vision, and more.

Commission-based earnings following the completion of your onboarding and apprenticeship period. Performance-based incentives that reward results and consistent growth. A flexible, self‑managed schedule.

A field‑based role with regular travel required throughout the Winnipeg Area and surrounding Manitoba territory. What You’ll Do Operate independently in the field while staying closely aligned with the YWT Sales Leadership Team. Identify, engage, and onboard new dealership partners, owning your assigned territory end‑to‑end.

Clearly communicate YWT’s value to key decision‑makers by positioning our solutions as a full‑suite strategic partnership. Build trusted relationships with your dealers’ Finance, Sales, Service, and Management teams. Deliver hands‑on training and support to ensure confident product adoption and dealer success.

Develop and execute a strategic territory plan to maximize growth and market penetration. Act as a subject‑matter expert on all YWT products and the competitive landscape. Travel regularly within your assigned territory.

What We’re Looking For We’re seeking a self‑motivated, driven professional who takes pride in how they do business and enjoys being on the road building meaningful partnerships and driving dealer profitability. Valid driver’s license and access to a reliable personal vehicle for regular in‑territory travel. Minimum of three (3) years of demonstrated success in automotive sales or finance is strongly preferred.

Resides in the Winnipeg, Manitoba. Experience working in an automotive dealership is a major asset; F&I, sales, or service. A strong track record of developing new business and consistently exceeding targets.

Confidence presenting to and influencing dealer principals, executives, and management teams. High independence, accountability, and drive – this field‑based role is ideal for someone who doesn’t want to be stuck behind a desk. Equal Opportunity YWT Dealer Services welcomes and encourages applications from people with disabilities.

Accommodations are available on request for candidates taking part in all aspects of the recruitment and selection process. #J-18808-Ljbffr