AI & Automation Lead

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Sr Lead, AI & Automation - Customer Support based in Canada.

This is a hands-on leadership role at the intersection of AI, automation, customer support, and knowledge management.

• Design, build, and deploy AI agents and automation workflows that address specific friction points across customer support operations, taking ownership of their architecture and implementation.
• Continuously identify repetitive tasks, manual handoffs, slow processes, and other operational friction, translating these opportunities into a prioritized AI and automation roadmap.
• Monitor and improve the quality and performance of AI solutions in production, including accuracy, tone, resolution rates, and appropriate human escalation.
• Stay current with developments in LLMs, agent frameworks, semantic search, and emerging AI technologies to identify opportunities for practical application.
• Partner closely with AI and transformation teams to align on technical architecture, capabilities, priorities, and implementation feasibility.
• Work directly with frontline support stakeholders and subject matter experts to understand operational challenges, validate solutions, and ensure new tooling works effectively in real-world environments.
• Represent customer support requirements in broader AI initiatives and translate company-wide AI direction into practical opportunities for support operations.
• Own the knowledge base and internal documentation ecosystem, ensuring information remains accurate, structured, governed, and useful for both humans and AI systems.
• Establish content, taxonomy, and knowledge-management practices that improve discoverability, answer quality, and agent performance.
• Analyze support data and AI performance to identify knowledge gaps and coordinate improvements to documentation and content.
• Own the end-to-end self-service experience for customers and prospects across guides and AI-powered answer tools, maintaining a high standard for accuracy, tone, relevance, and resolution.
• Analyze customer and prospect queries, search behavior, and unresolved questions to identify recurring themes, product opportunities, and content gaps.
• Partner with Product and Product Marketing to ensure recurring customer questions inform product improvements, positioning, and communication strategies.
• Lead a small team of knowledge and AI enablement specialists, setting priorities, coaching team members, conducting 1:1s, and developing their technical and professional capabilities.
• Establish and monitor performance metrics covering AI-assisted and self-service experiences, including accuracy, CSAT, deflection, handle time, and time saved.
• Track broader business outcomes such as retention and conversion to demonstrate the impact of AI and automation beyond support efficiency.
• Present performance insights, investment recommendations, and the AI/automation roadmap to leadership on a regular basis.

• 5+ years of experience in AI and automation implementation, support enablement, knowledge management, content strategy, or a related field.
• Hands-on experience with AI agents, LLMs, automation workflows, or similar technologies, with the ability to build solutions rather than simply oversee them.
• Demonstrated experience mentoring, managing, or leading individuals or small teams, formally or informally.
• Strong systems-thinking capabilities, with the ability to identify operational friction and design solutions around complete workflows rather than isolated tasks or documents.
• Experience owning customer self-service, support content, knowledge management, or related programs, ideally with accountability for both answer quality and insights generated from customer questions.
• Strong cross-functional collaboration skills, with the ability to work effectively with technical AI teams, support specialists, product teams, and business stakeholders.
• Ability to translate complex technical and operational concepts into clear priorities, requirements, and recommendations.
• Familiarity with customer support, CRM, AI, and automation platforms such as HubSpot, Help Scout, Talkdesk, Claude, Gumloop, or comparable tools.
• Strong analytical and problem-solving skills, with the ability to connect automation initiatives to measurable customer and business outcomes.
• Strong communication and stakeholder-management skills, including the confidence to present roadmaps, findings, and recommendations to leadership.
• Curiosity and enthusiasm for emerging AI and automation technologies, with a willingness to experiment, learn, and continuously improve.
• Comfort operating in a fast-paced, ambiguous environment where priorities evolve quickly and solutions need to be developed iteratively.
• Candidates who do not meet every listed qualification but bring strong relevant experience and enthusiasm for the role are encouraged to apply.