Customer Success Enablement Specialist (Knowledge Management & AI)

Octopusapp Inc.; Canada; Hybrid; CAD 72,000 - 97,000; Full time

Benefits offered by this job

Equity rewards

Health stipend

RRSP matching

Extended health insurance

Career development program

Job summary

Jobber seeks a Customer Success Enablement Specialist focused on Knowledge Management and AI. You will own and evolve a portfolio of knowledge assets, creating AI-ready content, SOPs, workflows, and enablement materials that empower Customer Success teams.

You’ll partner with Product, AI, Data, and subject matter experts to ensure knowledge remains accurate, discoverable, and scalable. The role emphasizes hands-on documentation, information architecture, and editorial judgment, with a path to

Qualifications

• Experience in knowledge management, technical writing, enablement, or a related field within a SaaS or customer-facing organization.

Responsibilities

• Create, maintain, and continuously improve knowledge assets throughout their lifecycle.
• Develop AI-ready knowledge including articles, SOPs, workflows, and playbooks.
• Translate product changes and operational updates into trusted knowledge for teams.
• Improve knowledge quality using QA findings, VOC insights, and AI performance signals.
• Support learning in the flow of work with onboarding resources and reference materials.
• Contribute to AI enablement across product, data, and customer success teams.
• Collaborate to document complex information clearly for both humans and AI.

Skills

Technical writing

Information architecture

Content design

Cross-functional collaboration

Documentation

Tools

Confluence

Guru

Notion

Helpjuice

Zendesk Guide

Intercom

GitHub Docs

Job description

Hybrid, Canada

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-management skills and the ability to provide clear status updates on tasks as assigned.

Experience preparing knowledge for AI-enabled experiences, including conversational & agentic AI, agent assist, LLM-based search, self-service, or other AI-powered knowledge systems.

Strong editorial judgment and a continuous improvement mindset, using customer feedback, search insights, QA findings, conversation intelligence, and AI performance signals to strengthen the quality and effectiveness of knowledge.

Excellent collaboration skills, with the ability to partner across Product, AI, Data, Customer Success, and subject matter experts to translate complex information into trusted knowledge.

Strong organization and prioritization skills, with the ability to manage an assigned portfolio of knowledge assets in a fast paced environment.

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 $71,700, a midpoint of $84,400, and a maximum salary of $97,100, designed to show the progression from learning the ropes to truly excelling.

We design our compensation to reflect each team member’s skills and experience in relation to the complexity of the role, ensuring a fair and competitive salary. Our range is intentionally broad to support both your growth and long-term impact. The higher end of the range is reserved for those who have demonstrated deep expertise and lasting contributions within the role, while offers below the midpoint reflect expected proficiency and strong potential with room to develop in the role. Some opportunities may be a lateral move and are not guaranteed a compensation bump. 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!