Then Jobber might be the place for you! We’re looking for a Senior Manager, Customer Success 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 will lead Jobber’s enablement function as a trusted partner and strategic business asset—not just a delivery team. You will architect the operating model, governance structures, and AI-embedded systems that allow Customer Success to scale quality without scaling headcount. You will be accountable for how the organization onboards, learns, retains knowledge, and measures quality across onboarding, support, and account management.
This is an AI-first role. That means you are not a passive user of AI tools—you are the person who designs how AI is embedded into the CS workflow: from how reps find answers in real time, to how knowledge infrastructure is structured to power AI agents, to how quality is measured and fed back into coaching. You will be responsible for the knowledge layer that makes AI work (“garbage in, garbage out” is your operating principle), and you will govern it with the same rigour as any other business-critical system.
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 functions from the ground up, owning the repeatable methodology behind the work, and using data, feedback, and intuition to level up both team performance and the customer experience.
The Senior Manager, Enablement, will focus on:
Function Architecture & Operating Model
Own the Enablement function’s operating model—not just its programs. Build and maintain a repeatable methodology, portfolio governance framework, and capacity management approach that holds without you in the middle.
Define and report on success metrics across all Enablement pillars: ramp time, QA score trends, knowledge engagement, CSAT, deflection rates, and AI agent performance.
Drive signal-driven leadership—using QA data, VoC insights, and call intelligence to iterate on strategy, not waterfall roadmaps.
AI Infrastructure & Knowledge Management
Own the knowledge management governance model as the foundational data layer for all AI initiatives—including agent design, LLM-based search, and IVR/voice bot content. KM quality is AI quality.
Design and govern AI-embedded enablement systems: define agent architecture, content quality standards, human-in-the-loop validation frameworks, and the feedback loops required to maintain accuracy through weekly product releases.
Partner with the KM team to drive governance of internal and external knowledge assets (playbooks, SOPs, Help Center articles) with the rigour required for AI readiness—not just human readability.
Lead deliberate adoption and optimization of existing AI tools.
Learning, Onboarding & Continuous Development
Design and deliver onboarding, upskilling, and continuous learning programs tailored to Customer Onboarding, Product Support, and Sales Expansion teams.
Lead and coach enablement team members in curriculum development, facilitation, and instructional design.
Integrate feedback from VoC, QA insights, and CSAT metrics into training evolution—including for AI-assisted workflows.
Quality Assurance
Lead QA strategy for onboarding and support interactions, including call reviews, chat/email evaluations, and structured feedback loops.
Align QA criteria with enablement outcomes and team performance standards; drive cross-functional calibration to ensure consistency.
Build QA not just as a scoring mechanism but as a coaching infrastructure—one that generates actionable signal, not just a number.
Cross-functional Partnership
Partner with Product, Product Marketing, Revenue Operations, Engineering and People teams to ensure readiness for product releases, campaigns, and feature changes at pace.
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 leading an enablement, L&D, or QA function inside a B2B SaaS organization with a fast product release cadence—demonstrated knowledge of relevant best practices, methodologies, and technologies.
Experience designing or governing AI-embedded enablement systems—including knowledge infrastructure as the data layer for AI agents, human-in-the-loop validation frameworks, and the ability to think at an architecture level, not just a tool-use level. You can speak to LLM-based natural language search, agent design logic, and data quality governance. Chatbot literacy is not sufficient.
Demonstrated ability to build an enablement function’s operating model from the ground up: methodology design, portfolio governance, capacity management, and feedback loops that create org-level leverage.
People management experience—you are comfortable leading, scaling, and coaching high-performing teams, and you understand the difference between managing a team and building a function.
Deep experience with LMS platforms, content tools (e.g., Notion, Confluence), QA frameworks, call intelligence tools, and product enablement practices.
A data-driven mindset and strong program management abilities, with the judgment to distinguish milestone-driven roadmaps from activity lists.
Excellent communication and facilitation skills—across live sessions, async formats, executive presentations, and documentation.
Strong business acumen and the ability to connect enablement decisions directly to retention, CSAT, and revenue outcomes.
A high level of curiosity, a passion for continuous improvement, and extremely strong analytical and problem-solving skills.
Note on AI Fluency: This is not a role for someone who has experimented with AI tools. It requires a leader who has designed or governed systems where AI is embedded in live workflows—and who can defend that architecture under scrutiny. Please reflect this accurately in your application.
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!
