Senior Lead, AI & Automation – Customer Support

Posted yesterday

Apply Now

Resume Score

Check how well your resume matches this job before you apply.

Sign in to check score

About the role

  • AI automation leader building support agents and knowledge systems for Jane’s healthcare SaaS platform. Leading enablement experts and improving customer self-service, efficiency, retention, and conversion.

Responsibilities

  • 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

Job title

Job type

Full Time

Experience level

Senior

Salary

CA$115,000 - CA$160,000 per year

Degree requirement

No Education Requirement

Location requirements

RemoteCanada

Report this job

Found something wrong with the page? Please let us know by submitting a report below.