# Director of Customer Service, Enablement and AI

**Company:** [Skylight](https://hotfix.jobs/companies/skylight)
**Location:** Remote
**Role:** Customer Success
**Salary:** $150k – $185k/yr
**Experience:** 5+ years
**Skills:** LLMs, AI Agents, Prompt Engineering, knowledge management, Vendor Management, Zendesk, metrics analysis, Change Management, sop development, Root Cause Analysis, qa automation, Intercom, decagon, sierra
**Posted:** 2026-07-27

> 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.

## Job Description

## 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).

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