Director, Sales Enablement in Kitchener

Do you believe enablement should be measured in ramp speed and revenue, not completion rates? Then Jobber might be the place for you! We’re looking for a Director, Sales Enablement to be part of our Sales Enablement & Operations department.

Jobber exists to help people in small businesses be successful. We work with small home service businesses, like your local plumbers, painters, and landscapers, to transform the way service is delivered through technology. With Jobber they can quote, schedule, invoice, and collect payments from their customers while providing an easy and professional customer experience.

Our culture of transparency, inclusivity, collaboration, and innovation has been recognized by Great Place to Work, Canada’s Most Admired Corporate Cultures, and more. Jobber has also been named on the Globe and Mail’s Canada’s Top Growing Companies list, and Deloitte Canada’s Technology Fast 50™, Enterprise Fast 15, and Technology Fast 500™ lists.

The team: Sales Enablement & Operations exists to make sure Jobber’s go-to-market org never has to choose between moving quickly and being ready. We build the systems, tools, and people development that turn strategy into execution.

The role: Reporting to the Sr. Director, Sales Enablement & Operations, the Director, Sales Enablement will lead Enablement Programs and make sure every seller at Jobber has what they need to win: the skills, the confidence, and the readiness to perform from day one and through every new launch.

The Director, Sales Enablement will:

• Set the strategy for onboarding, training, certification, and coaching across the sales org.
• Own ramp programs and certification standards across go-to-market roles.
• Lead enablement for new product, pricing, and process launches.
• Build structured, repeatable playbooks and coaching frameworks.
• Bring AI into how the team builds and delivers enablement.
• Partner with Product, Product Marketing, Sales leadership, and Customer Success.
• Define success beyond completion rates, and report on ramp time, certification pass rates, and downstream impact on pipeline and revenue.

To be successful, you should have:

• Extensive experience in sales enablement, revenue operations, or sales leadership.
• Demonstrated people leadership experience.
• A proven track record of leading enablement for product or pricing launches in a B2B SaaS environment.
• Hands‑on fluency with AI tools in enablement work itself.
• Experience building structured, scalable learning frameworks.
• Strong stakeholder management with director‑level and senior partners.
• Comfort operating with ambiguity and building infrastructure where none exists yet.
• Sharp written and verbal communication.
• A bias toward outcomes over activity.

Compensation: At Jobber, we believe that compensation should be transparent, fair, and reflective of your experience and growth. This role has a minimum annual salary of $181,400, a midpoint of $213,500, and a maximum salary of $245,500.

Location: The role is open to candidates based in one of our hub cities: Edmonton, Toronto, Vancouver, or Kitchener-Waterloo.

We believe that diverse teams perform better and that fostering an inclusive work environment is a key part of growing a successful team. We welcome people of diverse backgrounds, experiences, and perspectives. We are an equal opportunity employer, and we are committed to working with applicants requesting accommodation at any stage of the hiring process.