Sr Lead, AI & Automation - Customer Success

About the Role

Our Customer Success Operations team is the engine behind one of the most celebrated support experiences in healthcare tech. We sit at the intersection of technology, people, and purpose, building the systems, tools, and intelligence that allow our Support team to show up for healthcare practitioners in a way that feels genuinely human and consistently delightful.

This role is a hybrid builder-and-leader position. You'll be hands-on, designing and shipping agents that remove friction from our team's workflows, while also leading a small team and partnering closely with stakeholders across the Customer Team and AI Transformation Team to make sure the tooling actually lands. The goal is simple: free our teams from manual, high-friction work so they can spend their time on relationships and high-value work.

What Impact We’re Looking for You to Make

🤖 AI & Agent Building

• Design, build, and ship agents that solve specific friction points in Customer Team workflows.
• Continuously identify where friction lives across the support organization and build an agent roadmap.
• Own performance and quality of AI tooling in production: accuracy, tone, resolution rates, and human handoffs.
• Stay close to emerging trends in LLMs, agent frameworks, and semantic search.

🔗 Cross-Functional Partnership

• Work with the AI Transformation team to align on architecture, capability, and feasibility.
• Partner with Support stakeholders to understand real operational friction.
• Represent Support's needs in company-wide AI conversations.

📚 Knowledge Foundation

• Own the knowledge base and internal documentation, ensuring accuracy for both humans and AI.
• Build content and taxonomy practices for AI and human use.
• Use support data and agent performance to close knowledge gaps.

🎯 Customer & Prospect Self-Service Experience

• Own the end-to-end self-service experience across guides and AI answer tools.
• Maintain exceptional quality standards for answers (accuracy, tone, resolution rate).
• Analyze queries and search terms to surface product and content gaps.

⭐ Team Leadership

• Lead a small team of knowledge and AI enablement experts through priorities, 1:1s, and skills growth.
• Build a team capable of bridging technical AI work and human support operations.

📈 Impact & Measurement

• Track quality metrics for AI-assisted answers including accuracy and CSAT.
• Track efficiency metrics including deflection rate, average handle time, and time saved.
• Connect AI and automation work to downstream business impact like retention and conversion.

What Experience We Need

• 5+ years in AI/automation implementation, support enablement, or knowledge/content strategy with hands-on agent or LLM tooling experience.
• Ability to independently construct agents or automation workflows rather than just specifying them.
• Experience mentoring or leading others formally or informally.
• Strong systems thinker who views challenges through workflows and processes.
• Cross-functional communication skills spanning engineering and frontline support.
• Experience managing a self-service or customer content program.
• Familiarity with tools such as Hubspot, Help Scout, Talkdesk, Claude, and Gumloop.

Compensation & Benefits

• Annual salary range of $115,000 to $160,000 USD.
• Comprehensive benefits package included.