Director of Customer Service, Enablement and AI

About Skylight

Skylight is a technology startup focused on developing the operating system that simplifies family life. We are known for Skylight Calendar, a smart calendar embraced by millions of families and highly praised by Wired and the Wirecutter. Our latest offering, Calendar 2, has recently launched to excellent reviews. Our mission is to connect loved ones by delivering the simplest products and services to enhance family experiences. Founded by ex-venture capitalists and serial entrepreneurs, we have successfully grown a profitable company generating over $300 million in annual revenue without external investors, enabling us to prioritize creating beloved products.

We value intelligent, dedicated individuals passionate about creating meaningful products. Our team invents innovative solutions to support family life and parenting, and we invite you to join us in this endeavor.

Role Overview

This leadership position oversees artificial intelligence within our entire Customer Service department, balancing two key areas:

• Customer-facing AI: Responsible for maintaining and improving live AI agents that handle email, chat, and voice interactions by enhancing issue resolution quality, expanding capabilities, and providing round-the-clock coverage during peak times.
• Agent-enablement AI: Managing internal tools designed to enhance human team efficiency, including AI-assisted responses, troubleshooting guidance, quality assurance automation, knowledge management, intelligent routing, summarization, and insight extraction. Decisions include whether to develop tools internally or engage third-party vendors.

Our philosophy prioritizes customer resolution over mere deflection. AI is intended to eliminate repetitive tasks, allowing staff to focus on meaningful, empathetic interactions, especially for customers requiring additional care.

Key Responsibilities

• Expand the AI program to support doubling the company's growth without proportional increases in staffing by strategizing build-versus-buy options and holding vendors accountable to actual performance.
• Ensure high-quality live support by monitoring resolution rates, containment metrics, and customer satisfaction across all support channels; investigate root causes when AI underperforms and implement corrective measures.
• Maintain and enhance knowledge infrastructure by analyzing support tickets to identify gaps, managing taxonomy, and ensuring new product launches have AI-ready content from inception.
• Foster frontline employee trust by collaborating with support teams to implement AI tools, creating feedback loops, and authoring Standard Operating Procedures for human-AI interactions.
• Implement rigorous quality assurance and engineering practices treating AI prompts and updates like production software through use of test suites, pre-release failures, and phased rollouts.
• Quantify business impact by transparently reporting on return on investment, cost per contact, and resource savings compared to alternative hiring strategies using live tests to validate results.
• Fulfill a player-coach leadership role by actively engaging in hands-on execution with the existing AI support team while preparing the operational foundation for scaling.

Candidate Requirements

• Minimum of five years’ experience in customer service or operations support and program management, including extensive cross-functional project execution.
• Demonstrated experience managing and advancing mature AI and automation programs, emphasizing growth and optimization over initial development.
• Proven leadership of support channels across voice, chat, and email.
• Practical expertise with large language model tools, including prompt development, maintaining knowledge integrity, and evaluating AI output quality; coding skills not mandatory but reliance on vendor defaults is inadequate.
• Strong analytical capabilities in relevant metrics, understanding the limitations of deflection rates and complementary measurement approaches.
• Track record of successful frontline change management, effectively guiding teams through new technology adoption and earning positive feedback.
• Experience in systematic vendor selection and contract management.
• Excellent written communication skills for creating procedures, business documentation, and executive reports.
• Ability to work independently in ambiguous situations, proactively identifying issues and proposing solutions.

Preferred Qualifications

• Background in direct-to-consumer or combined hardware and software support environments, especially those with seasonal volume fluctuations.
• Hands-on experience with Zendesk as both agent and administrator.

Not Required

This position is operational leadership focused on utilization of AI tools rather than roles requiring engineering or data science expertise.

Benefits and Perks

• Attractive salary complemented by equity offerings.
• 401(k) plan with company matching.
• Budgets allocated for wellness, education, and home office needs.
• Comprehensive health, dental, and vision insurance plans.
• Significant autonomy to shape your work objectives.
• Unlimited paid time off.
• Company holidays observed on the first Friday of most months (excluding November, December, and January).

Diversity and Inclusion

Skylight is an equal opportunity employer intent on cultivating a diverse and inclusive workforce. All qualified candidates are considered regardless of race, color, religion, gender, sexual orientation, gender identity, age, national origin, disability status, veteran status, or other legally protected characteristics.

Location and Salary Information

We hire throughout the United States with specific listings for New York and Colorado. For candidates based in Colorado and California, the salary range for this role is between $150,000 and $185,000 annually, commensurate with experience. Employment decisions take into account any criminal history in compliance with applicable fair chance laws.

Additional Information

This position requires onsite work in the United States and offers the chance to contribute significantly to a thriving company focused on innovative family products.