Two Chicks With A Side Hustle

(Remote – U.S.) | 🕐 Schedule: Sunday–Thursday | 12:00 AM – 9:00 AM ET

🧾 About the Role
Calendly is hiring a Customer Support Specialist to join the team on our overnight shift. You’ll be the first line of defense for users across the globe, solving technical issues and providing a stellar customer experience via chat, email, and phone. If you’re a night owl with a passion for people, tech, and problem-solving, this is your chance to impact millions—while the world sleeps.


Position Highlights
• 💰 Hourly Pay: $19.62–$26.55 (based on geographic location)
• 📆 Schedule: Sunday through Thursday, 12:00 AM – 9:00 AM ET
• 🏠 Remote: 100% Remote (Eligible U.S. states only; see restrictions below)
• 🧭 Department: Customer Experience
• 🎁 Perks: Corporate bonus program, equity awards, full benefits package


📋 What You’ll Own
• Serve as the first point of contact for customers via live chat, phone, and email
• Troubleshoot user issues and provide clear, actionable solutions
• Become a Calendly product and scheduling industry expert
• Work autonomously and escalate technical issues appropriately
• Maintain accurate documentation and deliver exceptional communication
• Use metrics to track performance and contribute to support initiatives
• Regularly attend ticket audits and training for ongoing improvement
• Help users schedule better and smoother—day or night


🎯 Must-Have Traits
• 1+ year experience in SaaS or technical customer support
• Proficiency with live chat or phone-based support
• Technical troubleshooting and resourceful problem-solving skills
• Excellent time management and self-direction in remote environments
• Clear, empathetic verbal and written communication
• Passion for helping people and creating positive experiences
• Authorized to work in the U.S. (Calendly does not offer sponsorship at this time)


💻 Remote Requirements
• Must reside in an eligible U.S. state
Not eligible: AK, AL, CA, DE, HI, ID, IA, MT, ND, NE, RI, SD, WV
• Reliable home office setup with fast internet
• Comfortable working overnight shifts independently
• Willingness to embrace feedback and grow in a metrics-driven environment


💡 Why It’s a Win for Remote Night Owls
You’ll join a company that’s changing the way the world schedules. With flexible growth opportunities, deep product ownership, and a supportive remote culture, this role is perfect for those who love working overnight and making a global impact from their home base.


✍️ Call to Action
If you’re a proactive, curious, and self-motivated support pro who thrives after dark, apply now to be part of Calendly’s mission to simplify scheduling—and life—for millions.