Customer Service Team Lead

About Skylight

Skylight is an innovative technology startup dedicated to creating the operating system for families through products like Skylight Calendar, which is favored by millions and acclaimed by notable media. The company’s mission is to strengthen family connections by delivering simple, impactful products and services that enhance family life. Founded by experienced entrepreneurs and venture capitalists, Skylight has grown to a $300 million+ profitable business without external investors, nurturing a positive and customer-focused culture.

Role Overview

The Concierge Team Lead will oversee the day-to-day functioning and quality standards of the Concierge team, ensuring exceptional customer service is delivered via phone, chat, and email. This leadership role encompasses operational management, coaching team members, quality assurance, and performance oversight. The Team Lead primarily supports through mentorship, review, and escalation handling, engaging directly with customers in urgent or peak situations.

Responsibilities

• Manage operational coverage by ensuring adequate staffing and smooth execution across all support channels, monitor demand and adjust workflows as necessary.
• Serve as a close collaborator to the Supervisor by providing updates on team metrics, highlighting trends, and participating in performance discussions.
• Enhance service quality through one-on-one coaching and feedback sessions focused on communication style, accuracy, and efficiency to build team capability and confidence.
• Maintain thorough knowledge of product updates and support processes to effectively train, assist, and guide the team.
• Lead hiring, onboarding, and training efforts for new Concierge Agents, utilizing structured programs to ensure strong ramp-up.
• Coordinate team schedules and coverage during high-volume periods such as May and the November-January holiday season, including mandatory attendance during major holidays.
• Contribute to pilot initiatives and cross-departmental projects by facilitating the introduction of new tools and workflows, ensuring smooth adoption and gathering team feedback.

Schedule Details

• Role requires availability during nights and weekends.
• Team operates daily from 8 AM to 8 PM EST; leadership shifts last 8 hours within this period.
• Scheduled work follows Sunday-Thursday with Friday/Saturday off, or Tuesday-Saturday with Sunday/Monday off.
• Extended time off is restricted during peak seasons and key holidays.

Requirements

• Minimum of two years experience in customer support with demonstrated leadership skills.
• Excellent verbal and written communication, with particular attention to tone and detail.
• Familiarity with customer support tools such as Zendesk and Slack.
• Proven track record in coaching, training, and supporting team members in a dynamic environment.
• Strong organizational, multitasking skills, and self-motivated work approach.
• Collaborative, empathetic leadership style focused on team success.
• Comfortable using technology including Mac computers.
• Willingness to travel to in-person events quarterly or as needed.
• Reliable internet connection required.

Benefits

• Competitive salary accompanied by equity options.
• 401(k) matching programs.
• Budgets available for wellness, education, and home office improvement.
• Comprehensive health, dental, and vision insurance plans.
• Great autonomy in managing work responsibilities.
• Unlimited paid time off.
• Company holidays observed on the first Friday of each month except November through January.

Equal Opportunity and Compliance

Skylight embraces diversity and inclusiveness and considers all qualified applicants without discrimination based on legally protected characteristics. The company complies with applicable local laws regarding employment practices, including consideration of applicants with criminal histories as applicable by law. Specific salary offers for Colorado and California candidates start at $67,000, depending on experience.