Head of AI-Driven Customer Support & Automation

Jane Software Inc.; Canada; Hybrid; CAD 160,000 - 222,000; Full time

Job summary

Jane Software Inc. is seeking a Senior AI/Automation Leader to design and ship agents that streamline Customer Team workflows.

You will lead a small team, partner with AI Transformation and Support, and ensure the tooling lands effectively while focusing on knowledge foundations and self-service experiences. The role blends hands-on builder work with leadership, shaping a roadmap to reduce manual friction and free time for high‑value relationships with practitioners and patients.

Qualifications

• 5+ years in AI/automation implementation, support enablement, or knowledge/content strategy.
• Hands-on agent or LLM tooling experience preferred.
• Experience mentoring or leading others, formally or informally.
• Strong systems thinking; can design workflows, not just docs.
• Cross-functional collaboration with AI engineers and frontline teams.
• Experience owning a self-service or customer content program.

Responsibilities

• Design, build, and ship agents to remove friction in Customer Team workflows.
• Own performance, accuracy, tone, and escalation needs of AI tooling.
• Align architecture and feasibility with AI Transformation team.
• Own knowledge base and documentation for AI-enabled agents.
• Shape end-to-end self-service experiences across guides and AI tools.
• Lead a small team of knowledge and AI enablement experts.

Skills

AI/automation

Agent tooling

LLM tooling

Mentoring

Systems thinking

Cross-functional collaboration

Self-service content

Tools

Hubspot

Help Scout

Talkdesk

Claude

Gumloop

Job description

Jane Software Inc. is seeking a Senior AI/Automation Leader to design and ship agents that streamline Customer Team workflows.

You will lead a small team, partner with AI Transformation and Support, and ensure the tooling lands effectively while focusing on knowledge foundations and self-service experiences. The role blends hands-on builder work with leadership, shaping a roadmap to reduce manual friction and free time for high‑value relationships with practitioners and patients.