Senior Manager, Enablement & Knowledge SystemsJoin our Customer Success department to lead a high performing team and evolve our enablement function into a strategic knowledge and AI enablement engine.The RoleOwn systems, governance, and operating rhythms that ensure teams have the right knowledge, guidance, and support at critical moments.Key ResponsibilitiesOwn the operating model for Knowledge Management across Customer Success – governing intake, prioritization, ownership, publishing standards, and lifecycle management.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 principles, adapted to Jobber’s scale and pace.Define and report on KM health metrics – quality, freshness, findability, self‑service performance, and knowledge gaps – using analytics and AI signals.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.Own the knowledge layer that powers AI‑assisted Customer Success workflows: 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 to continuously improve AI performance.Monitor and improve AI performance – answer accuracy, source quality, containment/deflection, hallucination risk, fallback rates – and translate signals into fixes.Lead deliberate adoption of AI‑enabled workflows: determine when to trust AI, verify, and escalates.Design programs and rituals that help teams find, use, trust, and improve knowledge in the flow of work.Partner with Enablement, QA, and frontline leaders to translate knowledge gaps, quality trends, and AI insights into targeted coaching, communications, and performance support.Support onboarding and continuous learning by ensuring critical knowledge is accessible, current, role‑specific, and embedded where needed.Drive adoption of KM and AI‑enabled workflows through change management, stakeholder engagement, communications, and manager enablement.Partner with Product, Product Marketing, Revenue Operations, Engineering, Support, Onboarding, QA, and Enablement to maintain alignment of knowledge and AI systems with releases and business priorities.Act as strategic owner of knowledge flow 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 Leadership on how knowledge and AI reduce operational friction, improve consistency, increase self‑service, reduce time to answer, and scale quality without scaling complexity.Lead, coach, and grow a 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 the team, creating standards that last without ongoing oversight.Represent the roadmap, wins,



and needs to Customer Success leadership and cross‑functional stakeholders.QualificationsProven experience leading Knowledge Management, AI Enablement, Support Operations, Customer Experience Operations, or related function at a rapid‑paced B2B SaaS with rapid product release cadence.People management experience – comfortable leading, scaling, and coaching high‑performing teams, distinguishing content management from building a durable knowledge function.Deep knowledge of modern KM practices: lifecycle management, governance, taxonomy, metadata, health, quality standards, findability, source‑of‑truth management, and internal/external ecosystems.Experience designing or governing AI‑enabled workflows where knowledge quality directly impacts AI quality – agent assist, AI agents, LLM‑based search, self‑service, chatbots, voice bots, workflow automation – strong understanding of AI‑ready knowledge practices such as retrieval quality, content structure, feedback loops, 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.Data‑driven mindset and strong program management ability.Excellent communication and facilitation skills across async documentation, executive presentations, stakeholder alignment, and cross‑functional decision‑making.High curiosity, systems thinking, and continuous improvement orientation.LocationThe role is based in Canada and open to candidates in Edmonton, Toronto, Vancouver, or Kitchener‑Waterloo.CompensationMinimum annual salary:$132,400, midpoint:$155,700, maximum:$179,100. Salary reflects experience and growth. Base salary is part of a total compensation package that includes equity, health benefits, retirement savings matching, and wellness stipends.BenefitsExtended health benefits with fully paid premiums, RRSP/TFSA/FHSA matching, equity rewards, annual wellness stipends, retirement savings matching, talent development program with coaching and career development opportunities.EEO StatementWe 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 are committed to working with applicants requesting accommodation at any stage of the hiring process.#J-18808-Ljbffr

📌 Senior Manager, Enablement & Knowledge Systems - $132,400 - $179,100 A Year (Winnipeg)
🏢 Jobber
📍 Winnipeg