Customer Service Specialist

Description Skylight is a technology startup building the OS of the family. We make Skylight Calendar, the smart calendar loved by millions of families (plus Wired and the Wirecutter ). Our latest product is Calendar 2 , which just launched to rave reviews. Our mission is to connect loved ones by creating the world’s simplest products and services that improve family life. Our founders are former venture capitalists and serial entrepreneurs who have scaled this business to $300M+ in annual revenue while being completely bootstrapped and profitable . We get to grow a happy, healthy company focused on making products our customers love without investors breathing down our necks. Smart, hardworking people who care about making actually meaningful products love working here. People like you. We’re busy inventing new ways to simplify family life and help parents raise great kids – and we need your help! Come invent something new with us. We're looking for a Concierge Team Lead to manage day-to-day operations and quality across our Concierge team, ensuring consistent, high-quality support across phone, chat, and email. This role focuses on operational oversight, coaching, quality assurance, and performance management. You'll spend your time teaching, reviewing, and supporting others so they can deliver great customer experiences, stepping onto the frontline yourself only for escalations and emergencies. As Concierge Team Lead, you'll act as a key leadership partner to the Supervisor, keeping them informed on team performance, surfacing trends, and helping shape coaching conversations. You'll oversee coverage and workflow across all support channels, ensure onboarding and training set new Agents up for success, and connect regularly with Agents to review their work and reinforce quality standards. This role is ideal for someone who loves developing people, has a sharp eye for quality, and thrives on building strong, well-run teams in a fast-paced, customer-obsessed environment. Schedule Please note that availability for nights and weekends are required for this role. The Concierge Team operates seven days a week, from 8 AM to 8 PM EST. Leader shifts are scheduled in 8-hour blocks within that timeframe, with at least two days off each week. Lead schedules run Sunday-Thursday with Friday/Saturday off or Tuesday-Saturday with Sunday/Monday off. Our peak seasons are May and November through January, and all team members are expected to work during the weeks of Mother’s Day, Thanksgiving, and Christmas. Extended PTO is not granted during this time. 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. Benefits Our competitive compensation package includes: Competitive Salary + Equity Package 401K matching Wellness, learning, and home-office budgets Health, Dental & Vision Medical Plans Tremendous autonomy to set the direction of your work Unlimited PTO Company holidays on the first Friday of every month (Excluding November, December, and January) Equal opportunity employer Skylight is committed to building a diverse and inclusive team. All qualified applicants will be considered without regard to race, color, religion, sex, sexual orientation, gender identity or expression, age, national origin, disability, protected veteran status, or any other factor protected by applicable federal, state, or local laws. If you’re the best person for the job, we want you on board! We hire across the U.S., but for legal reasons, we have to list NY and CO separately. For Colorado-based candidates, the range being offered for this role is $67k based on experience and for California-based candidates, the range being offered for this role is $67k based on experience. Pursuant to the San Francisco Fair Chance Ordinance, we will consider employment for qualified applicants with criminal histories in a manner consistent with the requirements of this law. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.