Director, Sales Enablement

Job Description

Does enabling sales success & organizational impact at one of North America’s fastest-growing startups excite you?

Then Jobber might be the place for you! We’re looking for a Director, Sales Enablement to be part of our Sales department.

About Jobber:

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:

When it comes to ensuring our Sales teams are equipped to succeed, our Sales Enablement team is essential. This team provides the tools, training, content, and strategic insights to drive the success of our Account Executives, SDRs, and other sales functions.

The role:

Reporting to the VP, Sales, the Director, Sales Enablement will play a pivotal role in designing and leading initiatives that drive sales productivity and effectiveness. Balancing strategic leadership and hands-on execution, this role will develop, manage, and continuously enhance our sales enablement framework. Acting as a trusted advisor to both Senior and Sales Leadership, this role will ensure enablement efforts align with Jobber’s strategic goals and optimize all Sales performance.

The Director, Sales Enablement will:

• Define and drive the Sales Enablement strategy: Partner with Sales, Marketing, Revenue Operations, and Product teams to build a comprehensive enablement roadmap that aligns with Jobber’s strategic priorities.
• Design impactful training programs: Architect and oversee scalable, best-in-class onboarding, skills development and ongoing training programs across all levels and roles in the Sales team to achieve peak performance and accelerate time to productivity.
• Optimize sales content and resources: Champion the creation and management of high-impact sales collateral through a partnership with Marketing. You’ll help develop, manage, and distribute high-quality, easily accessible sales content and resources that enhance the buyer experience and ensure the Sales team is equipped to succeed at ever stage of the sales cycle.
• Implement sales tools and technology: Evaluate, implement, and optimize tools and platforms that enhance sales efficiency and insights, such as CRM systems and content management solutions to align with business objectives.
• Elevate internal career development: Develop training and career development programs that enable sales reps to navigate their careers at Jobber, preparing them for internal promotions and more senior roles within the organization.
• Lead and develop a high-performing team: Lead, coach, and develop Enablement Managers and Specialists to execute the enablement strategy effectively and achieve team objectives.
• Measure and refine initiatives: Define success metrics for enablement initiatives, regularly analyze performance, and adjust strategies as needed to meet organizational goals.
• Collaborate cross-functionally: Act as a liaison between sales and other departments to ensure alignment and collaboration on key initiatives.

To be successful, you should have:

• Proven experience in a senior/leadership-level Sales Enablement or related role within a scaling organization.
• Deep understanding of sales processes, methodologies, and enablement best practices.
• Demonstrated success in building and delivering effective enablement strategies and programs.
• Strong project management skills and ability to handle multiple priorities in a fast-paced environment.
• Excellent communication and collaboration skills with a proven ability to work cross-functionally.
• Proficiency with sales tools and technology (e.g., Salesforce, LMS, Highspot, or similar).
• Analytical mindset with a focus on data-driven decision-making.
• A passion for coaching, mentoring, and developing others.

Where you can expect to work:

Our product provides entrepreneurs the flexibility of working in their office or the field, and we offer that same opportunity to our employees. You will have the choice to work in either our Edmonton or Toronto offices or remotely anywhere within Canada. We’re committed to ensuring the best experience for all Jobberinos to do impactful work.

All interviews are currently being conducted virtually—via phone or video.