Customer Support Specialist - Part-Time (Remote, Pittsburgh)

About Skylight and Our Mission

Skylight is a technology startup dedicated to enhancing family life by creating the simplest and most effective products and services. We develop Skylight Calendar, a widely appreciated smart calendar for families, recognized by outlets like Wired and Wirecutter. Our latest release, Calendar 2, has received outstanding reviews. Our leadership includes former venture capitalists and serial entrepreneurs who have grown the company to over $300 million in annual revenue while remaining self-funded and profitable, fostering a positive and sustainable company culture without outside investor pressure.

Concierge Team Position Overview

We are currently hiring part-time, remote Concierge Team Agents based in the Greater Pittsburgh area. The role involves delivering exceptional customer support to users of our Skylight Calendar products. As part of the Concierge Team, you will maintain Skylight’s high standards for personalized and knowledgeable service, ensuring each customer interaction is handled with care and professionalism.

Schedule and Location Requirements

• This is a part-time role requiring between 16 to 29 hours weekly.
• Peak operational months are May; November through January, including mandatory work during the weeks of Mother's Day, Thanksgiving, and Christmas.
• Our team operates daily from 8 AM to 8 PM EST, with shifts of either 4 or 8 hours. Employees will have at least two days off each week.
• Nights and weekend availability is required.
• Applicants must reside in the Greater Pittsburgh region and be able to attend an in-person interview in our Shadyside office.
• Training sessions require availability for one of the following dates: August 30 (12-4 PM EST), September 1 (4-8 PM EST), or September 3 (12-4 PM EST).

Key Responsibilities

• Deliver personalized one-on-one customer service throughout the entire customer lifecycle, from purchasing to product setup and ongoing use.
• Engage with customers using phone, chat, email, and social media, managing an average of 6-8 interactions per hour, with potential increases to 10-12 based on complexity.
• Handle escalated issues involving Skylight's hardware and software challenges.
• Report recurring patterns or feedback to help proactively address emerging problems.
• Contribute to team projects aimed at enhancing customer experience and support goals.
• Participate in monthly in-person team-building activities at Skylight’s Pittsburgh co-working space.

Candidate Profile

• Empathetic and patient customer service professional skilled in clear, compassionate communication across multiple platforms.
• Adaptive team player comfortable with ambiguity and autonomous decision-making.
• Collaborative mindset understanding the dynamics of startup environments.
• Passionate about technology and thriving in fast-paced, evolving product settings.
• Organized, efficient, and capable of prioritizing urgent tasks effectively.
• Strong verbal and written communication skills, able to simplify complex concepts clearly.

Candidate Requirements

• Minimum of 2 years in high-volume frontline customer service roles, proficient in email, phone, chat, and social media support.
• Experience with Zendesk or comparable CRM platforms is essential.
• Patience and skill in guiding and educating customers.
• Comfortable working with Mac computers and Slack communication tools.
• Stable and reliable Wi-Fi connection is mandatory.
• Previous experience in an agile startup environment preferred.
• Proven ability to quickly learn new technologies and become a product expert.

Preferred Qualifications

• Background supporting customers through social media channels such as Facebook Meta, Instagram, TikTok, and Reddit.
• Experience in direct-to-consumer or e-commerce customer support.
• Familiarity with technical or digitally integrated product support.

Compensation and Benefits

• Hourly pay rate of $20.
• 64 hours of accrued sick leave annually to support employee well-being.
• Use of a loaned laptop and Skylight Calendar device provided upon joining the team.