Senior Manager, Customer Success Enablement

Do you want to impact the hardest working people in the world?

Then Jobber might be the place for you! We’re looking for a Sr. Manager, Enablement to be part of our Customer Success 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:

Our Customer Success team works together with other teams and stakeholders to bring our company values to life for our customers. By being humble, supportive, and truly giving a sh*t, the team ensures that our customers are successful in Jobber. This team thrives on meaningful and impactful communication with one another and with our customers and plays a significant role in the lives of entrepreneurs and business owners who utilize Jobber.

The Enablement team is a central function within Jobber’s Customer Success organization, supporting the growth and performance of Customer Onboarding, Product Support and Account Management. As a Center of Excellence, Enablement owns the programs, tools, and frameworks that drive operational excellence and skill development in these areas. We work cross-functionally to ensure that every team member—regardless of channel or customer type—has the knowledge, confidence, and support to deliver value.

The role:

As Senior Manager, Enablement , you’ll be a driving force behind the design and execution of enablement programs across employee onboarding, knowledge management, quality assurance, and continuous learning. You’ll play a pivotal role in shaping how our Customer Success teams onboard, grow, and show up for our customers across onboarding, support, and account management functions.

This is a highly autonomous, impact-oriented role—ideal for someone who thrives in ambiguity, moves quickly from insight to action, and brings fresh, creative thinking to solving complex problems. You’re energized by building programs from the ground up, collaborating cross-functionally, and using data, feedback, and intuition to level up both team performance and the customer experience.

You understand the inner workings of high-performing Success organizations and are ready to roll up your sleeves to build systems, content, and experiences that drive real results—whether it's a smoother ramp, a smarter knowledge base, or a more confident team on the front lines.

The Senior Manager, Enablement , will:

• Design and deliver onboarding, upskilling, and continuous learning programs tailored to the needs of Customer Onboarding, Product Support, and Sales Expansion teams.

• Coach Enablement team members in curriculum development, facilitation, and instructional design.

• Integrate feedback from Voice of Customer (VoC), QA insights, and CSAT metrics into training evolution.

• Oversee the creation, organization, and maintenance of internal and external knowledge assets (e.g., playbooks, SOPs, Help Center articles).

• Ensure knowledge materials are accurate, accessible, and in line with best industry best practice for technical writing

• Partner closely with Knowledge Base Managers and content specialists to drive strategy and efficiency in self-serve resources.

• Lead QA strategy for onboarding and support interactions, including call reviews, chat/email evaluations, and feedback loops.

• Align QA criteria with enablement outcomes and team performance standards.

• Drive cross-functional calibration sessions to ensure consistency and transparency.

• Define success metrics across each enablement pillar—ramp time, QA score trends, knowledge engagement, CSAT, and more.

• Report regularly on enablement impact to Success and cross-functional leadership

• Use data to iterate on training delivery, content structure, and coaching programs.

• Partner with Product, Product Marketing, Operations, and People teams to ensure readiness for product releases, campaigns, and feature changes.

• Influence and support change management efforts across supported functions.

• Ensure enablement alignment with business goals, team targets, and customer outcomes.

To be successful, you should have:

• Proven experience in enablement, L&D, or QA within a SaaS or customer-focused organization; demonstrated knowledge of relevant best practices, methodologies, and technologies

• Proven leadership in building enablement strategies that serve diverse functions (e.g., onboarding, support, sales).

• People management experience - you should be comfortable leading, scaling, and coaching high performing teams

• Deep experience with LMS platforms, content tools (e.g., Notion, Confluence), QA frameworks, and product enablement practices.

• A curiosity for AI, not just as a user, but as a builder to shape what Enablement at Jobber looks like

• A data-driven mindset and strong program management abilities.

• Excellent communication and facilitation skills—across live sessions, async formats, and documentation.

• Strong business acumen

• A high level of curiosity, and a passion for continuous improvement

• Extremely strong analytical and problem-solving skills

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.

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 $132,400 , a midpoint of $155,700 , and a maximum salary of $179,100 , 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!

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!