Senior Lead, AI & Automation – Customer Support

This is a fully remote position, open to applicants in Canada.

📋 Description

• Create, develop, and deploy agents to address workflow challenges within the Customer Team.

• Detect repetitive tasks, slow data retrievals, and manual transitions, transforming them into a strategic agent roadmap.

• Manage the performance and quality of production AI tools, focusing on metrics such as accuracy, tone, resolution rates, and human handoff protocols.

• Stay updated on new LLMs, agent frameworks, and semantic search technologies.

• Coordinate the architecture and capabilities with the AI Transformation team.

• Collaborate with Support stakeholders and subject matter experts to ensure agent behavior aligns with expectations.

• Advocate for Support requirements in organization-wide AI discussions and relay AI strategies back to the Support team.

• Oversee and maintain the knowledge base and internal documentation.

• Develop content and taxonomy practices that are accessible for both humans and AI.

• Leverage support data and agent performance metrics to identify and resolve knowledge gaps.

• Manage customer and prospect self-service experiences through guides and the AI answer tool.

• Examine customer and prospect inquiries, search terms, and unresolved queries.

• Direct product-related feedback to the Product team and collaborate with Product and Product Marketing departments.

• Lead a small team of knowledge and AI enablement specialists, prioritizing tasks, conducting 1:1s, and fostering skill development.

• Monitor AI/self-service quality, efficiency, retention, and conversion metrics.

• Present insights and roadmaps to leadership while recommending future investments.

⛳️ Requirements

• Minimum of 5 years in AI/automation implementation, support enablement, or knowledge/content strategy.

• Preferably possess hands-on experience with agent or LLM tooling.

• Capability to design an agent or automation workflow, rather than merely specifying one.

• Experience in mentoring or leading others, whether formally or informally.

• Strong analytical skills in systems thinking and workflow analysis.

• Cross-functional experience collaborating with AI engineers and frontline Drivers.

• Proven experience managing a self-service or customer content program.

• Familiarity with tools such as HubSpot, Help Scout, Talkdesk, Claude, Gumloop, and various AI/automation technologies.

• Must currently reside and work in Canada.

• Must be eligible to work in Canada without the need for employer sponsorship.

• No relocation, visa sponsorship, or support for third-party/employer-of-record employment is available.

🏝️ Benefits

• Comprehensive benefits package.

• Regular discussions on career development with your manager.

• Opportunities for compensation growth as experience and significant contributions increase.

• Access to tools, support, and an environment to explore, learn, and share AI discoveries.

• Remote-first work arrangement.