Director of Customer Service, Enablement and AI

Skylight is a technology startup focused on creating solutions that enhance family life. The Director of Customer Service, Enablement and AI will oversee AI initiatives in customer service, enhancing both customer-facing and internal tools to improve service quality and efficiency.

Responsibilities:

• 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
• Own resolution, containment, and CSAT across chat, email, and voice
• Run root-cause analysis when AI fails a customer and ship the fix
• Keep retrieval sharp by mining ticket logs for knowledge gaps, maintaining taxonomy, and ensuring Day-1 AI-ready content for all new product launches
• Partner with human support teams to roll out agentic tools, create feedback loops, and write the SOPs governing human-AI workflows
• Treat prompts and knowledge updates like production code using test suites, "break the bot" pre-releases, and staged rollouts
• Honestly report ROI, cost per contact, and capacity returned against hiring alternatives—validating performance through live testing
• 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 lead 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
• DTC/consumer or hardware+app support environment; seasonal volume experience
• Zendesk Agent and Admin experience