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.

• Sharp written and verbal communication.

• A bias toward outcomes over activity, and the judgment to know the difference.

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, designed to show the progression from learning the ropes to truly excelling.

We design our compensation to reflect each new hire’s skills, experience against the complexity of the role, ensuring a fair and competitive salary. Our range is intentionally broad to support growth and long-term impact, with fully established hires typically starting around the midpoint. The higher end of the range is reserved for those who have demonstrated deep expertise and lasting contributions, while offers below the midpoint reflect strong potential with room to develop. This approach ensures that compensation aligns with both an individual’s current capabilities and their opportunity for future growth.

Base salary is just one part of a total compensation package that will include equity rewards, annual stipends for health and wellness, retirement savings matching, and an extended health package with fully paid premiums for body and mind. Your professional growth matters to us too! You’ll have access to a dedicated talent development program that includes career coaching and opportunities for career development.

We believe in transparency and open conversations about compensation. If you have any questions about our approach, we’re happy to discuss them throughout the hiring process!

Location:

We believe great collaboration is intentional, and sometimes that means coming together in person to build, brainstorm, and connect. To support this, the role is open to candidates based in one of our hub cities: Edmonton, Toronto, Vancouver, or Kitchener-Waterloo.

What you can expect from Jobber:

• A total compensation package that includes an extended health benefits package with fully paid premiums for both body and mind, matching in RRSP, TFSA or FHSA, and stock options.

• A dedicated Talent Development team and access to coaching, learning, and leadership programs to help you grow your career, reach your goals, and unlock your full potential.

• A unique opportunity to build, grow, and leave your impact on a $400-billion industry that has no dominant player...yet.

• To work with a group of people who are humble, supportive, and give a sh*t about our customers.

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.

A bit more about us:

Job by job, we’re transforming the way service is delivered. Your lawn care provider, home cleaning service, plumber or painter could use Jobber to better connect with their customers, save time in the office, invoice faster, and get paid! We’re bringing tens of thousands of people together with technology to deliver billions of dollars a year in services to happy customers. Jobber exists to help make these small businesses successful, and when they’re successful we all win!