Director of Customer Service, Enablement and AI

🕒 July 27

⛰️ Colorado, New York – Remote

⛰️ Colorado – Remote 🗽 New York – Remote

💵 $150k - $185k / year

⏰ Full Time

🔴 Lead

💝 Customer Support

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Skylight

WebsiteLinkedInAll Job Openings

11 - 50 employees

Founded 2015

🏭 Manufacturing

📣 Marketing

💼 Consulting

💰 Venture Round on 2020-09

Manufacturing • Marketing • Consulting

Skylight is a company that offers digital picture frames and calendar devices designed to bring families together and simplify household organization. Their products include a Skylight Frame, which allows users to share photos and videos with loved ones through an anti-glare touchscreen display, and the Skylight Calendar, which displays everyone's schedules in one interactive device. These products are easy to set up, do not require a subscription, and aim to keep users connected and organized. Skylight frames and calendars are touted as great gifts, especially for keeping family memories alive and ensuring ease of communication among multiple family members.

📋 Description

• 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 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

🏖️ Benefits

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