Customer Success Representative

This position is posted by Jobgether on behalf of a partner company. We are currently looking for a Customer Success Representative in Canada.

This role is centered on driving real-world adoption and long-term value for users in a complex B2B2C environment where success is not just about onboarding, but about enabling independence. You will work directly with equipment dealerships and help them become fully self-sufficient in using and scaling a digital platform across their internal teams. Rather than acting as a permanent point of contact, you will focus on building internal champions who can sustain engagement and drive usage long after your involvement. The role blends field engagement, training, relationship-building, and strategic enablement across multiple dealership roles and functions. You will translate business goals into practical workflows that resonate with service teams, parts staff, and leadership. This is a highly autonomous, impact-driven position for someone who thrives on empowerment over dependency and measurable adoption outcomes.

In this role, you will be responsible for enabling dealership success through training, adoption strategy, and ongoing customer empowerment.

• Identify, develop, and support internal champions within dealerships who will drive long-term platform adoption.
• Deliver onboarding and training sessions designed to build self-sufficiency rather than ongoing reliance on external support.
• Understand dealership operations and end-customer needs, connecting both perspectives to platform value and usage.
• Monitor adoption and engagement metrics, proactively identifying friction points and enabling teams to overcome blockers independently.
• Build strong, trust-based relationships that encourage open communication on performance, needs, and improvement opportunities.
• Develop scalable enablement resources such as playbooks, guides, and training content tailored to different dealership roles.
• Capture and share success stories and best practices to accelerate adoption across the broader customer base.
• Act as a structured feedback loop to product teams, translating field insights into actionable, prioritized input.
• Support clear, user-friendly communication of product updates and enhancements for non-technical audiences.

Requirements:

The ideal candidate has strong experience in customer-facing roles within B2B2C or SaaS environments and excels at driving adoption through influence and enablement.

• Experience in customer success, account management, enablement, or similar roles in SaaS, agriculture, or equipment dealership environments.
• Strong understanding of dealership operations, including service, parts, and field-level decision-making processes.
• Proven ability to influence without authority and drive behavioral change across customer organizations.
• A “train-the-trainer” mindset focused on scalability and long-term independence of customer teams.
• Experience building or delivering enablement materials such as guides, presentations, or training content.
• Excellent communication skills, with the ability to engage both frontline workers and leadership stakeholders.
• Comfort working in remote, self-directed environments with accountability for outcomes.
• Willingness to travel approximately 25% to customer sites, including dealerships and operational locations.
• Strong analytical mindset to track adoption trends and identify improvement opportunities.

Benefits:

• Competitive compensation package with performance-based components.
• Employee share ownership (ESOP) opportunities.
• Remote-first work environment with flexible arrangements.
• Opportunity to work closely with leadership in a high-growth, entrepreneurial setting.
• Direct exposure to how AI and technology are transforming the agriculture and equipment dealership industries.
• Collaborative, learning-focused culture that values autonomy and impact.
• Meaningful travel opportunities to engage directly with customers in the field.