Customer Success Enablement Specialist (Knowledge Management & AI)

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

Then Jobber might be the place for you! We are looking for a Customer Success Enablement Specialist (Knowledge Management & AI) to join 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 the entrepreneurs and business owners who use 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 Customer Success Enablement Specialist , you create and maintain the trusted knowledge that powers Jobber's Customer Success teams and the AI experiences that support them. Reporting to the Senior Manager, Enablement & Knowledge Systems , your focus is technical writing, content design, and knowledge management, ensuring information is clear, discoverable, and optimized for both people and AI. Working within the Enablement team, you partner closely with Product, AI, Data, Customer Success, and subject matter experts to create and maintain the knowledge that powers Customer Success workflows, in-flow learning, conversational & agentic AI, agent assist, search, self-service, and other AI-enabled customer experiences.

This is a hands-on knowledge management role in an AI-first Customer Success organization. The knowledge you create is more than documentation. It forms the trusted knowledge layer that enables Customer Success teams to find accurate answers and powers AI systems to deliver reliable, contextual support. By creating high quality, structured, and AI-ready knowledge, you help improve customer experiences, strengthen AI performance, and enable Jobber to scale support through both people and technology.

In this role, you own a portfolio of knowledge assets from creation through ongoing maintenance, ensuring they remain accurate, well structured, discoverable, and optimized for both human use and AI retrieval. You continuously improve your content alongside product, process, and customer changes, applying established knowledge management and AI readiness standards. The quality of the knowledge you own directly contributes to content quality, AI performance, and release readiness, supporting the overall health of Jobber's knowledge ecosystem.

This is a hands-on role for someone who enjoys bringing structure to complexity and takes pride in creating knowledge that helps both people and AI perform at their best. You bring strong technical writing and information architecture skills, exercise sound editorial judgment, and use customer, operational, and AI performance signals to continuously improve the quality, usability, and effectiveness of the knowledge you own.

The Customer Success Enablement Specialist will:

Own a portfolio of knowledge assets: Create, maintain, and continuously improve knowledge assets throughout their lifecycle, ensuring they remain accurate, discoverable, version controlled, and aligned with Jobber's knowledge management and AI readiness standards.

Create trusted, AI-ready knowledge: Develop knowledge base articles, SOPs, workflows, playbooks, and enablement content that supports Customer Success teams and AI-enabled experiences. Apply technical writing, information architecture, taxonomy, metadata, and content standards to optimize knowledge for both people and AI.

Translate change into knowledge: Partner with Product, AI, Data, Customer Success, and subject matter experts to turn product releases, process updates, and operational changes into trusted knowledge that keeps Customer Success teams and AI experiences current.

Continuously improve knowledge quality: Use QA findings, Voice of Customer insights, search analytics, frontline feedback, and AI performance signals to identify knowledge gaps, improve content, validate AI readiness, and strengthen the quality of your portfolio.

Support learning in the flow of work: Create and maintain role-specific onboarding resources, reference materials, and performance support content that helps Customer Success teams learn, adapt, and perform confidently.

Contribute to AI enablement: Partner across Product, AI, Data, Customer Success, and Enablement to support AI-powered workflows, validate knowledge quality, and improve the knowledge layer that powers conversational & agentic AI, agent assist, search, self-service, and other AI-enabled experiences.

To be successful, you should have:

Experience in knowledge management, technical writing, enablement, or a related field within a SaaS or customer-facing organization, with a track record of creating and maintaining high quality knowledge content using platforms such as Confluence, Guru, Notion, or Helpjuice, grounded in established knowledge management practices such as Knowledge-Centered Service (KCS).

Hands-on experience administering modern help desk and knowledge base software, such as Zendesk Guide, Intercom, Help Scout, or Document360, with familiarity with HTML and CSS for custom formatting and basic Markdown highly preferred.

Hands-on experience with Git-based documentation workflows, a Docs as Code approach where content is authored, version controlled, and peer reviewed in GitHub, which the team uses actively.

Strong technical writing, information architecture, and content design skills, with a critical eye for structuring information. You organize complex technical hierarchies, taxonomy, metadata, tags, and content standards so that dry, multi-layered workflows stay highly digestible for people and optimized for AI retrieval.

Technical curiosity and aptitude, with comfort diving into platform settings, reading API documentation, and capturing clean, annotated screenshots or GIFs that make guides visually clear.

General knowledge of technical disciplines, such as coding, software design, servers, databases, networks, cloud, certificates, and middleware, enough to document technical concepts accurately and credibly.

Experience owning the end-to-end documentation creation process, with strong time