Director of Customer Service, Enablement and AI

New
S
SkylightTechnology Startup
United StatesFull-TimeDirector
Salary$150-185k based on experience
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Job Details

Experience
5+ years in CS/ Operations support, CS/Operations program management, with 5+ years of project implementation and major cross-functional programs
Required Skills
Data AnalysisChange ManagementZendesk

Requirements

  • 5+ years of experience in Customer Service operations or support program management.
  • 5+ years of experience in project implementation and managing major cross-functional programs.
  • Proven experience owning, scaling, and optimizing programs leveraging 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 quality evaluation.
  • Deep metrics fluency with the ability to explain and pair deflection rates with other success indicators.
  • Proven frontline change management experience in transitioning teams to new tooling.
  • Experience with structured vendor evaluation and management.
  • Strong written communication skills for documentation, business cases, and executive updates.
  • Ability to operate independently in ambiguous environments and propose solutions.

Responsibilities

  • Scale support capacity for company growth through AI and automation while making strategic build-vs-buy decisions.
  • Drive performance metrics including resolution, containment, and CSAT across chat, email, and voice channels.
  • Manage knowledge infrastructure by maintaining taxonomy, mining ticket logs, and preparing AI-ready content.
  • Partner with human support teams to roll out agentic tools, create feedback loops, and establish SOPs.
  • Enforce QA and engineering discipline by treating prompts like production code using test suites and staged rollouts.
  • Measure and report business ROI, cost per contact, and capacity optimization.
  • Execute as a player-coach to support the AI operations team while scaling the function.
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$150-185k based on experience
Apply Now