Sr Lead, AI & Automation - Customer Support

Jobgether; Canada; On-site; CAD 115,000 - 160,000; Full time

Benefits offered by this job

Remote-first with distributed teams

Comprehensive benefits package

Career development and growth

Opportunity to shape AI strategy

Global customer impact

Job summary

Jobgether seeks a Sr Lead, AI & Automation - Customer Support based in Canada to lead the design, deployment, and governance of AI-powered support tools. You will own the knowledge base, build automation workflows, and partner with AI, Product, and Support teams to reduce repetitive work while improving accuracy and customer satisfaction.

The role blends hands-on technical work with team leadership in a fast-growing SaaS environment.

Qualifications

• 5+ years of experience in AI and automation implementation, support enablement, knowledge management, or a related field.
• Hands-on experience with AI agents, LLMs, automation workflows, or similar technologies, with the ability to build solutions.
• 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.
• 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.

Responsibilities

• Design, build, and deploy AI agents and automation workflows that address friction points across customer support operations, owning architecture and implementation.
• Translate opportunities into a prioritized AI and automation roadmap by identifying repetitive tasks and slow processes.
• Monitor and improve AI quality and performance in production, including accuracy, tone, and escalation rates.
• Stay current with LLMs, agent frameworks, and semantic search to identify practical applications.
• Lead a small team of knowledge and AI enablement specialists and develop their capabilities.
• Own the knowledge base and internal documentation ecosystem, ensuring accuracy and governance.
• Establish content, taxonomy, and knowledge-management practices to improve discoverability and agent performance.
• Own end-to-end self-service experiences across guides and AI-powered answers, ensuring high accuracy and relevant responses.

Skills

AI & automation leadership

Team leadership

Cross-functional collaboration

Knowledge management

Program management

Understanding of AI tools

Tools

HubSpot

Help Scout

Talkdesk

Claude

Gumloop

Job description

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.
You’ll design and launch intelligent agents that remove repetitive work and help support teams focus on high-value customer relationships.
The role combines technical building with team leadership, requiring you to move comfortably between AI tooling, support operations, and business strategy.
You’ll own the quality and effectiveness of AI-assisted and self-service experiences, from knowledge foundations to customer-facing answers.
You’ll work closely with AI, Product, Support, and other cross-functional teams to identify friction, prioritize opportunities, and turn ideas into production-ready solutions.
Success will be measured through improvements in accuracy, customer satisfaction, efficiency, retention, and conversion.
This is an opportunity to shape how a high-growth SaaS organization uses AI to create a faster, smarter, and more human support experience.

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.