Customer Support Specialist, Part-Time - Weekend Availability Required

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.

About the Job

We’re hiring Part-Time Weekend Concierge Team Agents in the Greater Pittsburgh Region! We're seeking experienced customer service professionals to join our Customer Service Concierge Team and deliver exceptional support to our Skylight Calendar customers. This role is key to supporting Skylight as we grow and redefine what outstanding customer service looks like for our Calendar customers. As a Concierge Agent, you’ll uphold Skylight’s high standards for customer service, ensuring every interaction reflects the care, expertise, and attention our customers deserve. Compensation for this position is $20/hour.

Schedule

• This is a part-time position and weekly schedules range between 16 to 29 hours.
• 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.
• The Concierge Team operates seven days a week, from 8 AM to 8 PM EST. Shifts are scheduled in 4- or 8-hour blocks within that timeframe, with at least two days off each week.
• Priority will be given to candidates with the widest availability. Please note that nights and weekends are required.

To be eligible, you must reside in the Greater Pittsburgh, Pennsylvania Region and be available to schedule an in-person interview at our office in Shadyside.

Responsibilities

• Provide bespoke, 1-1 customer service for our Skylight Calendar and Frame customers through all phases of their customer journey from purchase to activation to set up and continued use of their devices.
• Engage with customers daily through high-volume phone, chat, email, and social media platform interactions. On average, you’ll support 6–8 customers per hour, though volumes may increase to 10–12 per hour depending on the complexity and nature of the inquiries.
• Support escalated customer issues involving complex hardware and software challenges with Skylight devices.
• Flag any patterns you notice in tickets or customer feedback so the team can stay ahead of emerging issues.
• Be a supportive peer and thought partner with our Customer Service Team Leads, providing coverage as needed for our core and troubleshooting customer service teams.
• Contribute to project-based work as needed to support team goals and enhance the customer experience.
• Ability to meet for in-person work days for team-building with the CS Leadership team and other Skylight employees located in Pittsburgh monthly in our local co-working office.

Who You Are

• A highly empathetic, caring customer service professional with a proven ability to communicate clearly and compassionately with customers across omni-channel customer service
• A nimble team-player who is comfortable with ambiguity, willing to test and iterate, and operate with autonomy
• Collaboratively minded, understanding the interconnected nature of departments in a startup environment
• Passionate about technology and energized by fast-paced, constantly evolving products and environments
• Excellently organized, with an ability to prioritize time-sensitive tasks and work with efficiency
• Strong written and verbal communicator who can convey complex ideas with clarity

Requirements

• 2+ years of high-volume, front-line customer service experience, with demonstrated ability to manage workload efficiently and proficiency in email, phone, chat, and social media support.
• Must have experience with Zendesk or a similar Customer Relationship Management (CRM) system
• Exhibits patience and attentiveness when listening to feedback and excels at teaching and guiding others
• Strong communication skills across email, phone, and chat, delivering clear, professional, and engaging interactions with customers and team members alike
• Previous experience working in an agile startup environment
• Demonstrated talent for rapidly mastering new technology and becoming a product expert
• A consistent, reliable Wi-Fi connection is required for this role
• Must be comfortable working on a Mac and communicating in the Slack platform.

Nice to Have

• Experience supporting customers on Social Media platforms such as Meta, Instagram, TikTok, and Reddit through ad comments, posts, and direct messages.
• Previous experience working with a direct-to-consumer (DTC) or e-commerce brand.
• Experience providing customer support for a technical or digitally connected product.

Benefits

• At Skylight, we care about our team. We offer 64 hours of accrued sick time annually to ensure you have time to rest, recharge, and care for yourself.
• Upon hire, you’ll be provided with a loaned laptop and a loaned Skylight Calendar to ensure you have the tools needed to succeed in your role.