Skylight needs a people-first leader who can protect quality while keeping a high-volume support team sharp, confident, and consistent. You’ll coach, QA, train, and manage coverage so every customer interaction feels like Skylight, not a ticket factory.
About Skylight
Skylight builds simple consumer products that connect families, including Skylight Frame and Skylight Calendar. They’re bootstrapped, profitable, and customer-obsessed, with $180M+ in annual revenue.
Schedule
- Remote (U.S.)
- Full-time
- Tuesday–Saturday (Sundays and Mondays off)
- Focus on peak coverage planning for high-volume periods (Q4, Mother’s Day)
What You’ll Do
- Lead performance management for Calendar Concierge agents to maintain strong quality, efficiency, and engagement KPIs
- Coach and develop agents through ongoing feedback, performance conversations, and targeted growth plans
- Oversee Quality Assurance across Zendesk tickets, live chat, and social support; use insights to improve training and workflows
- Own hiring, onboarding, and training for new Concierge agents, ensuring fast ramp and long-term success
- Monitor schedule compliance and help identify staffing needs; step in during high-volume periods as needed
- Manage customer-facing programs and initiatives that improve the support experience and stay on-brand
- Report on trends and team performance, flagging opportunities and guiding improvement efforts
- Partner cross-functionally with product, operations, and support stakeholders while advocating for customers and agents
What You Need
- 3+ years of customer support experience, including leadership/supervisory responsibility
- Strong written and verbal communication skills with a sharp eye for tone and detail
- Experience with CRM support platforms (Zendesk or similar)
- Experience supporting customers via social platforms (e.g., Reddit, Meta)
- Proven ability to coach, train, and support team members in a fast-paced environment
- Highly organized, self-motivated, and comfortable juggling multiple priorities
- Collaborative, empathetic leadership style rooted in helping others succeed
Benefits
- Competitive salary + equity package
- 401(k) matching
- Wellness, learning, and home-office budgets
- Health, dental, and vision plans
- Tremendous autonomy to set the direction of your work
- Unlimited PTO
- Company holiday on the first Friday of every month (excluding November, December, and January)
For candidates in CO and CA, the listed pay is $85,000 (based on experience). If you want a leadership seat where quality and coaching actually matter, this one’s a strong swing.
If you’re ready to lead from the front and build a team that customers feel in their bones, this is your lane.
Happy Hunting,
~Two Chicks…