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Jane
AI & Machine Learning 7h ago

AI & Automation Lead, Customer Success Operations

Jane
CanadaCanada
Full-time
$115,000 - $160,000
Senior-Level

Job Description

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What Impact We’re Looking for You to Make

🤖 AI & Agent Building

  • Design, build, and ship agents that solve specific friction points in the Customer Team workflows, architecting how they work rather than just configuring off-the-shelf tools.

  • Continuously identify where friction lives across the support organization (repetitive tasks, slow lookups, manual handoffs) and turn that into an agent roadmap.

  • Own performance and quality of AI tooling in production: accuracy, tone, resolution rates, and where a human needs to step back in.

  • Stay close to what's emerging in LLMs, agent frameworks, and semantic search.

🔗 Cross-Functional Partnership

  • Work with the AI Transformation team to align on architecture, capability, and what's feasible now versus later.

  • Partner with Support stakeholders and the team themselves to understand where the real friction is.

  • Bring in subject matter experts across Support Ops to validate agent behaviour in their domain before it ships.

  • Represent Support's needs in company-wide AI conversations, and bring company AI direction back to Support.

📚 Knowledge Foundation

  • Own the knowledge base and internal documentation, keeping it accurate and well-governed as the substrate agents and Drivers both rely on.

  • Build content and taxonomy practices that make information usable by both humans and AI, not just searchable.

  • Use support data and agent performance to find and close knowledge gaps.

🎯 Customer & Prospect Self-Service Experience

  • Own how customers and prospective customers find answers to their questions, end to end, across guides and the AI answer tool.

  • Set and hold the exceptional quality bar for those answers: accuracy, tone, and whether the response actually resolves the question. Ensuring results are as good as our world class team.

  • Analyze what customers and prospects are asking (queries, search terms, unresolved questions) to surface patterns worth acting on.

  • When the answer is missing or wrong, that's a knowledge or content gap to close. When the real fix is in the product itself, that's feedback to route to Product.

  • Partner with Product and Product Marketing so recurring "not yet customer" questions inform what we build and how we message it, not just what we document.

Team Leadership

  • Lead a small team of knowledge and AI enablement experts: set priorities, run 1:1s, and grow their skills, including agent-building capability.

  • Build a team that can move between deep AI/technical work and the people side of Support without losing either.

📈 Impact & Measurement

  • Track quality metrics for AI-assisted and self-service answers, including accuracy and CSAT, to make sure automation holds the same bar as our team.

  • Track efficiency metrics, including deflection rate, average handle time, and Driver time saved, to show where friction has actually been removed.

  • Track downstream business impact, including retention and conversion, to connect AI/automation work to outcomes beyond Support.

  • Present findings and roadmap to leadership regularly; make the case for where to invest next.

What Experience We Need

  • 5+ years in AI/automation implementation, support enablement, or knowledge/content strategy, ideally with hands-on agent or LLM tooling experience rather than just oversight of it.

  • Comfortable being the builder: you can actually construct an agent or automation workflow, not just spec one for someone else.

  • Experience mentoring or leading others, formally or informally.

  • Strong systems thinker: you see friction and think in workflows, not just documents.

  • Genuinely cross-functional: you're as comfortable in a room with AI engineers as you are with frontline Drivers.

  • Experience owning a self-service or customer content program, ideally where you were accountable for both the quality of the answers and what customer questions revealed about product gaps.

  • Familiarity with tools we use (Hubspot, Help Scout, Talkdesk, Claude, Gumloop etc.) and a real appetite for AI/automation tooling.

If you don’t meet every single qualification but are excited about this role, we’d still love to hear from you.

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Jane (operating via jane.app) is a premier, cloud-based practice management and clinical documentation platform engineered to fundamentally eliminate the administrative friction of running allied health and multidisciplinary clinics. Founded in 2012 in North Vancouver, British Columbia, the enterprise was born out of a real-world need to manage the complex operational demands of a modern wellness clinic. Moving far beyond traditional, single-specialty electronic health records (EHR), Jane natively unifies online booking, customized charting, multi-discipline scheduling, secure telehealth, and integrated payment processing into a single, beautifully designed ecosystem. The company is trusted by over 200,000 practitioners globally, empowering physiotherapists, massage therapists, chiropractors, and mental health counselors to run their businesses efficiently and focus entirely on patient care. Under the hood, their technology core ensures strict regulatory compliance (including HIPAA and PIPEDA) while leveraging robust cloud architectures to streamline complex insurance billing, intake forms, and multi-location management. Capturing massive market acceleration and functioning as a highly intuitive operating system for the health and wellness sector, Jane remains a definitive cornerstone of modern healthcare technology, empowering the helpers to deliver exceptional care with a completely frictionless administrative backend.

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