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SkylightSkylightUnited States

Director of Customer Service, Enablement and AI

Lead AI initiatives across customer service at Skylight, scaling AI agents for email/chat/voice and building internal agent-enablement tools. Requires 5+ years scaling AI/automation programs in support operations, hands-on LLM fluency, metrics expertise, and change management experience.

150k – 185k/yr
Remote5+ YOECustomer Success

About the role

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.
  • 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.
  • 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.
  • Led voice, chat, and email support channels.
  • Hands-on fluency with LLM-based tools: prompt iteration, knowledge hygiene, evaluation of output quality.
  • Deep metrics fluency.
  • Proven frontline change management.
  • Structured vendor evaluation and management experience.
  • Strong written communication.
  • 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.

Benefits

  • Competitive Salary + Equity Package.
  • 401K matching.
  • Wellness, learning, and home-office budgets.
  • Health, Dental & Vision Medical Plans.
  • Tremendous autonomy.
  • Unlimited PTO.
  • Company holidays on the first Friday of every month (Excluding November, December, and January).

Skills

LLMsAI AgentsPrompt Engineeringknowledge managementVendor ManagementZendeskmetrics analysisChange Managementsop developmentRoot Cause Analysisqa automationIntercomdecagonsierra

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