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Senior Manager, Enablement & Knowledge Systems

Jobber

Remote · US

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About this role

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 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 https://www.youtube.com/watch?v=EkfZmHrRLx4&list=PLoktA_D-2UEnxMLfCe93bANKXVXd2bdN8&index=24.

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.

- Build a scalable knowledge operating system that supports support delivery, onboarding, self-service, product readiness, AI-assisted workflows, and consistent customer experiences.

- Define and implement the end-to-end knowledge lifecycle: capture, structure, validate, publish, activate, measure, archive, and continuously improve internal and external knowledge assets.

- 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, includin

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