Sr Lead, AI & Automation - Customer Support

Accountabilities:

• • 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.

  Requirements

  • 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.

  Benefits

  • Annual salary range of $115,000–$160,000 CAD, with compensation progression tied to experience, impact, and career development.
  • Transparent compensation practices and regular career development conversations.
  • Comprehensive benefits package.
  • Remote-first working environment with a distributed team across Canada, the US, and the UK.
  • Opportunity to work at a high-growth SaaS organization serving more than 70,000 businesses and 250,000+ practitioners.
  • Significant opportunity to shape how AI and automation are used across customer support and the broader organization.
  • Support for experimentation, learning, and adoption of emerging AI tools and technologies.
  • Collaborative, customer-focused culture emphasizing impact, curiosity, adaptability, resilience, and continuous learning.
  • Opportunity to lead and develop a team while remaining deeply hands-on with AI and automation initiatives.
  • Work focused on improving the daily experience of healthcare practitioners and the businesses they serve.