Director, Sales Enablement

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. Running a small business today isn’t like it used to be—the way we consume and deliver service is changing rapidly, technology is evolving, and customers expect more. That’s why we put the power and flexibility in their hands to run their businesses how, where, and when they want!

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. With an Executive team that has over thirty years of industry experience of leading the way, we’ve come a long way from our first customer in 2011—but we’ve just scratched the surface of what we want to accomplish for our customers .

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: how we forecast and plan, how we pay and motivate, how our tech stack works for reps instead of against them, and how every seller gets better at their craft. The team is organized into peer pillars: Sales Operations, Revenue Technology, Sales Planning & Operations, and Enablement Programs.

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. You’ll lead a team of five to six, as a peer to the leads of Sales Operations, Revenue Technology, and Sales Planning & Operations. You’re accountable for outcomes, not activity — whether reps are actually ready, whether launches actually land in the field, and whether the enablement investment shows up in ramp speed, pipeline, and revenue.

The Director, Sales Enablement will:

Set the strategy for onboarding, training, certification, and coaching across the sales org, and build, manage, and upskill a team of enablement managers and practitioners.

Own ramp programs and certification standards across go-to-market roles, and hold the bar on what “certified and ready” actually means.

Lead enablement for new product, pricing, and process launches, building workback plans that trace every training, content, and certification milestone back from the launch date.

Build structured, repeatable playbooks and coaching frameworks, and keep them current as products, segments, and motions change.

Bring AI into how the team builds and delivers enablement — content creation, coaching feedback loops, practice and roleplay, knowledge access — and into what reps are taught to use in their own workflow.

Partner with Product, Product Marketing, Sales leadership, and Customer Success so enablement priorities match what the business needs next, and launches land with sales rather than at sales.

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, including building and running onboarding, training, or certification programs at scale.

Demonstrated people leadership experience, including managing managers, and a track record of developing your own team’s skills alongside the field’s.

A proven track record of leading enablement for product or pricing launches in a B2B SaaS environment, with workback plans that hold up against a real launch timeline.

Hands-on fluency with AI tools in enablement work itself: content generation, coaching and roleplay, and knowledge management.

Experience building structured, scalable learning frameworks rather than one-off training events.

Strong stakeholder management with director-level and senior partners across Product, Marketing, and Sales leadership, and the ability to influence roadmap and go-to-market timing rather than only execute against it.

Comfort operating with ambiguity and building infrastructure where none exists yet.