Director of Customer Service, Enablement and AI

Skylight is a technology startup building the OS of the family. We make Skylight Calendar, the smart calendar loved by millions of families (plus Wired and the Wirecutter). Our latest product is Calendar 2, which just launched to rave reviews.

Our mission is to connect loved ones by creating the world’s simplest products and services that improve family life. Our founders are former venture capitalists and serial entrepreneurs who have scaled this business to $300M+ in annual revenue while being completely bootstrapped and profitable. We get to grow a happy, healthy company focused on making products our customers love without investors breathing down our necks.

Smart, hardworking people who care about making actually meaningful products love working here. People like you. We’re busy inventing new ways to simplify family life and help parents raise great kids – and we need your help! Come invent something new with us.

This role owns AI across our entire Customer Service operation, on two fronts with equal weight:

1. Customer-facing AI — Own and strengthen our existing live AI agents across email, chat, and voice: raising resolution quality, expanding what they can safely handle, and carrying 24/7 coverage through seasonal spikes
2. Agent-enablement AI — internal tooling that makes our human team faster and better: agent-assist and drafting, AI guided troubleshooting, QA automation, knowledge management, smart routing, summarization, insights mining. Determine if we build tools in house or vet and hire third party vendors.

We are explicit about our philosophy: we optimize for resolution, not deflection. AI at Skylight exists to remove robotic work from humans and to make the human moments better, especially for customers who need patience and care.

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.

Skylight is a technology startup building the OS of the family. We make Skylight Calendar, the smart calendar loved by millions of families (plus Wired and the Wirecutter). Our latest product is Calendar 2, which just launched to rave reviews.Our missi...

• 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

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.

Skylight is a technology startup building the OS of the family. We make Skylight Calendar, the smart calendar loved by millions of families (plus Wired and the Wirecutter). Our latest product is Calendar 2, which just launched to rave reviews.

Our mission is to connect loved ones by creating the world’s simplest products and services that improve family life. Our founders are former venture capitalists and serial entrepreneurs who have scaled this business to $300M+ in annual revenue while being completely bootstrapped and profitable. We get to grow a happy, healthy company focused on making products our customers love without investors breathing down our necks.

Smart, hardworking people who care about making actually meaningful products love working here. People like you. We’re busy inventing new ways to simplify family life and help parents raise great kids – and we need your help! Come invent something new with us.

This role owns AI across our entire Customer Service operation, on two fronts with equal weight:

1. Customer-facing AI — Own and strengthen our existing live AI agents across email, chat, and voice: raising resolution quality, expanding what they can safely handle, and carrying 24/7 coverage through seasonal spikes
2. Agent-enablement AI — internal tooling that makes our human team faster and better: agent-assist and drafting, AI guided troubleshooting, QA automation, knowledge management, smart routing, summarization, insights mining. Determine if we build tools in house or vet and hire third party vendors.

We are explicit about our philosophy: we optimize for resolution, not deflection. AI at Skylight exists to remove robotic work from humans and to make the human moments better, especially for customers who need patience and care.

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.

Skylight is a technology startup building the OS of the family. We make Skylight Calendar, the smart calendar loved by millions of families (plus Wired and the Wirecutter). Our latest product is Calendar 2, which just launched to rave reviews.Our missi...

• 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

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.