Skylight

Customer Support Team Supervisor – Calendar

Skylight

full-time

Posted on:

Location Type: Remote

Location: United States

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Salary

💰 $90,000 per year

About the role

  • - 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.

Requirements

  • - 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
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)
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
quality assurancecoachingtrainingcustomer supportperformance managementonboardingprogram managementKPI managementworkflow refinementcustomer communication
Soft Skills
leadershipcommunicationorganizationcollaborationempathyself-motivationdetail-orientedmulti-taskingadvocacysupportive