Senior Lead, AI & Automation – Customer Support

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Jane.app

WebsiteLinkedInAll Job Openings

201 - 500 employees

🏥 Healthcare

💼 Consulting

⚕️ Healthcare Insurance

Healthcare • Consulting • Healthcare Insurance

Jane. app is a comprehensive practice management software designed for healthcare practitioners. Its platform includes features such as online booking, billing, and scheduling, with integrated telehealth capabilities that are HIPAA, PIPEDA, and GDPR compliant. Jane. app also offers customizable charting and reporting tools, payment processing options, and secure data storage solutions for multi-location practices. Additionally, their software is tailored for various types of healthcare clinics, providing an intuitive, web-based interface that improves clinic operations and patient experiences. The system is designed to simplify administrative tasks and enhance the efficiency of running a healthcare practice.

📋 Description

• Design, build, and ship agents for Customer Team workflow friction points • Identify repetitive tasks, slow lookups, and manual handoffs and turn them into an agent roadmap • Own production AI tooling performance and quality, including accuracy, tone, resolution rates, and human handoff points • Monitor emerging LLMs, agent frameworks, and semantic search • Align architecture and capabilities with the AI Transformation team • Partner with Support stakeholders and subject matter experts to validate agent behaviour • Represent Support needs in company-wide AI discussions and communicate AI direction back to Support • Own and govern the knowledge base and internal documentation • Build content and taxonomy practices usable by humans and AI • Use support data and agent performance to identify and close knowledge gaps • Own customer and prospect self-service answer experiences across guides and the AI answer tool • Analyze customer and prospect queries, search terms, and unresolved questions • Route product-related feedback to Product and partner with Product and Product Marketing • Lead a small team of knowledge and AI enablement experts, including priorities, 1:1s, and skills development • Track AI/self-service quality, efficiency, retention, and conversion metrics • Present findings and roadmap to leadership and recommend future investment

🎯 Requirements

• 5+ years in AI/automation implementation, support enablement, or knowledge/content strategy • Hands-on agent or LLM tooling experience preferred/ideally • Ability to construct an agent or automation workflow, not just specify one • Experience mentoring or leading others, formally or informally • Strong systems-thinking and workflow analysis • Cross-functional experience working with AI engineers and frontline Drivers • Experience owning a self-service or customer content program • Familiarity with HubSpot, Help Scout, Talkdesk, Claude, Gumloop, and AI/automation tooling • Must currently live and work in Canada • Must be eligible to work in Canada without employer sponsorship • No relocation, visa sponsorship, or third-party/employer-of-record employment support

🏖️ Benefits

• Comprehensive benefits package • Regular career development conversations with manager • Compensation growth as experience and meaningful contribution increase • Tools, support, and space to explore, learn, and share AI discoveries • Remote-first work arrangement