Then Jobber might be the place for you! We’re looking for a Senior Manager, Enablement & Knowledge Systems 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 and Product Support. 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 & Knowledge Systems, you will lead a high performing team and the evolution of Jobber’s enablement function into a strategic knowledge and AI enablement engine for Customer Success. You will own the systems, governance, and operating rhythms that ensure our teams have the right knowledge, guidance, and support in the moments that matter—whether they are onboarding a customer, resolving a support issue, navigating a product change, or using AI to move faster with confidence.
This is an AI-first enablement role, with knowledge management at its core. You are not simply rolling out tools or creating content; you are designing the knowledge infrastructure, governance, feedback loops, and adoption practices that make AI reliable, useful, and trusted. You will help define how knowledge powers LLM-based search, agent assist, AI agents, self-service, IVR/voice bot content, and real-time support experiences. KM quality is AI quality.
This is a highly autonomous, impact-oriented role—ideal for someone who thrives in ambiguity, can move quickly from strategy to operating rhythm, and brings both systems thinking and hands-on execution. You are energized by building from 0 to 100, creating standards that hold without you in the middle, and using data, frontline feedback, customer outcomes, and AI performance signals to continuously improve how teams learn, find answers, make decisions, and deliver value to customers.
The Senior Manager, Enablement & Knowledge Systems will focus on:
Knowledge Management Strategy & Operating Model
Own the operating model for Knowledge Management across Customer Success — governance, intake, prioritization, ownership, publishing standards, and lifecycle management from capture through continuous improvement.
Establish a KM governance model grounded in KCS (Knowledge-Centered Service) principles, adapted pragmatically to Jobber's scale and pace.
Define and report on KM health metrics — quality, freshness, findability, self-service performance, and knowledge gaps — using search analytics, frontline feedback, and AI performance signals to drive priorities.
Knowledge Architecture, Taxonomy & Content Quality
Own the structure and quality of Jobber's knowledge ecosystem, including playbooks, SOPs, Help Center content, and AI-facing sources.
Build and maintain the content model, taxonomy, tagging strategy, metadata standards, and source-of-truth practices required to make knowledge findable, reusable, measurable, and AI-ready.
Partner with Product, Support, Onboarding, and Engineering to translate product changes into trusted, actionable knowledge at release pace.
Identify and close knowledge gaps by analyzing search failures, escalations, customer friction, and AI answer failures.
Ensure knowledge is designed for both human usability and machine readability, including structure, chunkability, metadata, canonical sources, and retrieval performance.
AI Enablement & Knowledge Infrastructure
Own the knowledge layer that powers AI-assisted Customer Success workflows, including agent assist, LLM-based search, AI agents, IVR/voice bot content, and self-service.
Partner cross-functionally to define AI enablement requirements — content readiness, retrieval quality, governance, permissions, escalation paths, and human-in-the-loop validation.
Develop AI readiness standards for knowledge assets, including structure, chunkability, metadata, canonical sources, freshness, source traceability, access controls, and retrieval performance.
Create feedback loops between AI outputs, frontline users, customer outcomes, and knowledge owners so AI systems improve continuously rather than decay over time.
Monitor and improve AI performance — answer accuracy, source quality, containment/deflection, hallucination risk, and fallback rates — and translate signals into fixes.
Lead deliberate adoption of AI-enabled workflows: when to trust AI, when to verify, when to escalate, and how to feed improvement signals back into the system.
Knowledge Activation & Adoption
Design programs and rituals that help Customer Success teams find, use, trust, and improve knowledge in the flow of work.
Support onboarding and continuous learning by ensuring critical knowledge is accessible, current, role-specific, and embedded where teams need it most.
Drive adoption of KM and AI-enabled workflows through change management, stakeholder engagement, communications, and manager enablement.
Cross-functional Partnership & Change Leadership
Partner with Product, Product Marketing, Revenue Operations, Engineering, Support, Onboarding, QA, and Enablement teams to ensure knowledge and AI systems stay aligned with product releases, workflow changes, customer needs, and business priorities.
Act as the strategic owner for how knowledge flows across Customer Success—from product change to internal readiness, customer-facing content, AI-assisted support, and continuous improvement.
Influence cross-functional stakeholders to adopt clear ownership, governance, and feedback loops for knowledge and AI-enabled workflows.
Advise Customer Success leadership on how knowledge and AI can reduce operational friction, improve consistency, increase self-service, reduce time to answer, and scale service quality without scaling complexity.
People Leadership
Lead, coach, and grow an established team of knowledge management and enablement professionals, setting goals, growth paths, and performance expectations.
Own team rituals — 1:1s, performance reviews, planning cycles — that keep the team aligned and developing.
Prioritize and allocate team capacity across strategic initiatives and operational demands.
Build organizational capability in KM and AI-enablement practices through your team, creating standards that hold without you in the room.
Represent the team's roadmap, wins, and needs to Customer Success leadership and cross-functional stakeholders.
To be successful, you should have:
Proven experience leading Knowledge Management, AI Enablement, Support Operations, Customer Experience Operations, or a closely related function at a fast paced B2B SaaS or technology organization with a fast product release cadence.
People management experience—you are comfortable leading, scaling, and coaching high-performing teams, and you understand the difference between managing content and building a durable knowledge function.
Deep knowledge of modern KM practices, including knowledge lifecycle management, content governance, taxonomy, metadata, knowledge health, content quality standards, search/findability, source-of-truth management, and internal/external knowledge ecosystems.
Experience designing or governing AI-enabled workflows where knowledge quality directly impacts AI quality, such as agent assist, AI agents, LLM-based search, self-service, chatbots, voice bots, or workflow automation. You have a strong understanding of AI-ready knowledge practices like retrieval quality, content structure, feedback loops, and hallucination risk.
Experience with knowledge platforms, help centres, content management tools, AI support tools, search analytics, QA/call intelligence inputs, and product release enablement practices.
A data-driven mindset and strong program management ability, with the judgment to distinguish outcomes, signals, and operating rhythms from activity lists.
Excellent communication and facilitation skills across async documentation, executive presentations, stakeholder alignment, and cross-functional decision-making.
A high level of curiosity, systems thinking, and continuous improvement orientation, with the ability to balance strategic design with hands-on execution.
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!
