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Director of Customer Service, Enablement and AI

19 minutes ago
United States
Full-time
Lead
AI (Artificial Intelligence)
Software Development
LLM
Apply Now

Skylight / Skylight Frame

Skylight makes consumer technology products for families, primarily the Skylight Frame digital picture frame and the Skylight Calendar smart family calendar. Its core pitch is helping families share photos, schedules, and reminders.

Consumer electronics
51-200
View All Jobs 15

Description

  • Own the roadmap to scale support capacity for 2x company growth without linear headcount.
  • Manage customer-facing AI across email, chat, and voice to improve resolution quality, safe handling, and 24/7 coverage.
  • Own resolution, containment, and CSAT across support channels and run root-cause analysis when AI fails customers.
  • Manage knowledge infrastructure by identifying knowledge gaps, maintaining taxonomy, and ensuring new launches are AI-ready on day one.
  • Partner with human support teams to roll out agent-assist tools, build feedback loops, and write SOPs for human-AI workflows.
  • Evaluate build-vs-buy decisions and manage third-party vendors such as Decagon, Sierra, and Intercom Fin.
  • Treat prompts and knowledge updates like production code through test suites, staged rollouts, and pre-release testing.
  • Measure and report ROI, cost per contact, and capacity returned versus hiring alternatives.
  • Work hands-on as a player-coach while helping build the foundation for the function to scale.

Requirements

  • 5+ years in customer service or operations support, including 5+ years of project implementation and major cross-functional programs.
  • Experience owning, scaling, and optimizing an existing program using AI and automation tools.
  • Experience leading voice, chat, and email support channels.
  • Hands-on fluency with LLM-based tools, including prompt iteration, knowledge hygiene, and output evaluation.
  • Strong metrics fluency, including understanding why deflection rate alone is insufficient.
  • Proven frontline change management experience with tooling transitions.
  • Structured vendor evaluation and management experience.
  • Strong written communication for operating procedures, business cases, and executive updates.
  • Comfort operating independently, spotting ambiguity, and proposing solutions.
  • Preferred experience in DTC/consumer or hardware-plus-app support environments, including seasonal volume.
  • Preferred Zendesk Agent and Admin experience.
  • Engineering or data science background is not required.

Benefits

  • Competitive salary plus equity package.
  • 401(k) matching.
  • Health, dental, and vision medical plans.
  • Wellness, learning, and home-office budgets.
  • Unlimited PTO.
  • Company holidays on the first Friday of every month, excluding November, December, and January.
  • Tremendous autonomy to set the direction of your work.
  • Salary range of $150k-$185k based on experience for Colorado and California candidates.

Interested in this position?

Apply directly on the company website

Apply Now

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