Customer Service - Team Lead

Skylight is a technology startup building the OS of the family, and they are seeking a Concierge Team Lead to manage day-to-day operations and quality across their Concierge team. The role focuses on operational oversight, coaching, quality assurance, and performance management to ensure high-quality support across various channels.

Responsibilities:

• Own Operational Coverage Ensure phone, chat, and email channels are consistently staffed and running smoothly. Monitor volume and coverage across shifts, adjust as needed, and keep the team aligned on daily priorities. Step into the work on escalations or to support peak times of business
• Act as Leadership Support to the Supervisor Serve as a close partner to the Supe, keeping them informed on how the team is performing. Share observations, flag emerging trends, and contribute directly to coaching conversations and performance management decisions
• Drive Quality Through Coaching Connect with Agents during shifts or one-on-one to review their work, provide feedback, and reinforce best practices across tone, accuracy, and efficiency. Focus on building each Agent's skills and confidence so quality holds up consistently
• Maintain Product and Process Expertise Stay deeply informed on Calendar product updates and workflows so you can train others effectively and answer escalated questions. Use this expertise to teach others and to guide the team when issues get complex
• Support Hiring, Training, and Onboarding Play a lead role in hiring, training, and onboarding new Concierge Agents. Implement structured onboarding plans, guide new hires through key workflows, and ensure they ramp with confidence
• Support Peak Season Operations Help manage team coverage and staffing during key high-volume periods such as Q4 and Mother's Day. Ensure the team is prepared, aligned, and supported when volume is highest
• Support Pilots and Cross-Functional Initiatives Contribute to pilots or special projects by helping roll out new tools, workflows, or support models to the team. Gather feedback from Agents and share it upward to help improve the rollout experience

Requirements:

• 2+ years of experience in customer support, with demonstrated leadership abilities
• Strong written and verbal communication skills, with an eye for tone and detail
• Experience with support platforms like Zendesk and Slack
• Proven ability to coach, train, and support team members in a fast-paced environment
• Highly organized, self-motivated, and comfortable managing multiple priorities
• Collaborative and empathetic leader, committed to helping others succeed
• Comfortable with technology and experience working on a Macbook
• Ability to travel to in-person events quarterly or as business needs arise
• A reliable wifi connection is required for this role