Customer Support Team Supervisor - Calendar

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.

Concierge Team Supervisor

We’re looking for a Full-Time, Remote Calendar Support Team Supervisor to lead a team of customer support agents, known as our Calendar Concierge Team. This role focuses on the performance management of Concierge agents to ensure the team is providing high-quality customer interactions. This management role will also onboard and train new and tenured agents.

As a supervisor, you’ll be responsible for making sure team quality is upheld across all aspects of customer communication and that KPIs in quality, efficiency, and engagement stay on track through ongoing feedback and performance management. You’ll oversee quality assurance for Zendesk tickets and chat, monitor social media platform support, and lead onboarding and training efforts. You’ll also support customer-facing programs and initiatives that help the Concierge team better serve our customers.

You’ll play a key role in supporting Concierge team coverage — helping to identify staffing needs, ensuring scheduling compliance, and stepping in during high-volume periods. Your efforts will help maintain a consistent, high-quality customer experience across all channels.

In addition, you’ll take the lead on reporting, using data to identify trends, flag opportunities for improvement, and guide performance conversations. In this role, you'll be a strong cross-functional partner, staying aligned with major initiatives and current priorities, and serving as a go-to expert across the org.

This role is ideal for someone with deep experience in the leadership and performance management of front line customer service agents, and thrives in a fast-paced, customer-obsessed environment.
Please Note: The schedule for this role is Tuesday-Saturday with Sundays and Mondays off.

• Drive Team Quality and Performance:
  Maintain high standards across all customer communication channels (chat, email, social, etc.), ensuring KPIs — including schedule compliance — are consistently met. Provide regular coaching and feedback to support agent growth and performance. Partner with Team Leads to identify coaching needs, performance trends, and opportunities for improvement.
• Oversee Quality Assurance:
  Lead quality assurance efforts for Zendesk tickets, live chat, and social media responses. Use QA insights to drive training, refine workflows, and reinforce best practices across the team.
• Lead Hiring, Onboarding, and Training:
  Own the full lifecycle of hiring, onboarding, and training for new Concierge team agents. Delegate day-to-day training responsibilities as appropriate while maintaining ownership of the overall structure, content, and quality of the onboarding experience. Ensure agents ramp quickly, feel supported, and are set up for long-term success.
• Manage Customer-Facing Programs:
  Own and evolve customer-facing initiatives and programs that help the Concierge team better serve our users. Ensure content is clear, helpful, on-brand, and that participation and scheduling align with broader team goals.
• Act as a Cross-Functional Partner:
  Serve as a key partner across teams, staying aligned with evolving product, operations, and support initiatives. Represent the Concierge team in cross-functional conversations, advocating for both customer and agent needs.

Support Peak Season Coverage and Engagement:
Lead planning and execution of team coverage during high-volume periods such as Q4 and Mother’s Day. Ensure the team stays engaged, well-supported, and aligned to meet increased customer demand with high-quality care.

• 3+ years of experience in customer support, with demonstrated leadership or supervisory experience
• Strong written and verbal communication skills, with an eye for tone and detail
• Experience with CRM support platforms such as Zendesk
• Experience providing direct support to customers via Social Media platforms such as Reddit and Meta
• 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

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)

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 $85k, and for California-based candidates, the range being offered for this role is $85k 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.