Director of Customer Service, Enablement and AI

What You'll Do

Scale the Program: Own the roadmap to scale support capacity for 2x company growth without linear headcount. Make smart build-vs-buy decisions and hold vendors (Decagon, Sierra, Intercom Fin) to live performance, not sales demos

Drive Live Performance: Own resolution, containment, and CSAT across chat, email, and voice. Run root-cause analysis when AI fails a customer and ship the fix

Manage Knowledge Infrastructure: Keep retrieval sharp by mining ticket logs for knowledge gaps, maintaining taxonomy, and ensuring Day-1 AI-ready content for all new product launches

Build Frontline Trust: Partner with human support teams to roll out agentic tools, create feedback loops, and write the SOPs governing human-AI workflows

Enforce QA & Engineering Discipline: Treat prompts and knowledge updates like production code using test suites, "break the bot" pre-releases, and staged rollouts

Measure Business Impact: Honestly report ROI, cost per contact, and capacity returned against hiring alternatives—validating performance through live testing

Lead as Player-Coach: Execute hands-on alongside our current AI support team while laying the foundation to scale the function

Requirements

• 5+ years in CS/ Operations support, CS/Operations program management, with 5+ years of project implementation and major cross-functional programs
• You've owned, scaled and optimized an existing program leveraging AI and automation tools. Scaling and seeing a program to maturity matters more here than just the 0→1 experience
• You've led voice, chat, and email support channels
• Hands-on fluency with LLM-based tools: prompt iteration, knowledge hygiene, evaluation of output quality. You don't need to code, but "I just used the vendor defaults" is disqualifying
• Deep metrics fluency: you can explain why deflection rate alone is a vanity metric and what you'd pair it with
• Proven frontline change management — you've brought skeptical teams through a tooling transition and they'd say good things about how you did it
• Structured vendor evaluation and management experience
• Strong written communication; you'll be writing the operating procedures, business cases, and exec updates
• You are comfortable operating independently, spotting ambiguity and proposing solutions

Nice-to-haves

• DTC/consumer or hardware+app support environment; seasonal volume experience
• Zendesk Agent and Admin experience

Explicitly Not Required

• Engineering or data science background. This is an operations leadership role that uses AI, not an AI research or coding role