Senior Technical Support Representative

Technical Support Representative — CorksyRemote (US) | Must work Pacific Time hours | Full-TimeCorksy is a modern commerce and point-of-sale platform built for wineries. We power direct-to-consumer shipping, wine club management, tasting room reservations, and compliance — all in one place. Our customers are wineries who care deeply about their craft, and we care just as deeply about helping them succeed.The RoleAs a Technical Support Representative, you are the first line of help for our winery clients. When something isn't working — a POS terminal, a shipping label, a wine club charge — you're the person who jumps in, figures it out, and gets them back on track. You'll handle incoming questions across email, chat, and phone, troubleshoot real issues, and make sure every interaction leaves the client feeling taken care of. This role is fully remote, but working Pacific Time hours is essential.What You'll Do

• Respond to client support requests across email, chat, and phone in a timely, friendly way
• Troubleshoot issues across the Corksy platform — POS, DTC shipping, wine club, reservations, and compliance features
• Diagnose hardware and integration problems (card readers, receipt printers, label printers, shipping carriers)
• Document issues clearly and escalate complex bugs to the product and engineering teams
• Write and maintain help articles, FAQs, and internal troubleshooting guides
• Track recurring problems and share patterns with the team to improve the product
• Guide clients through setup, configuration, and best practices

What We're Looking For

• Able to work standard business hours in Pacific Time — this is a requirement for the role
• Eligible to work in the United States (fully remote)
• 4+ years in a technical support, help desk, or customer-facing troubleshooting role
• 2+ years of wine industry experience (winery, distributor, hospitality, or wine tech)
• Strong problem-solving skills and patience under pressure
• Clear, friendly written and verbal communication — able to explain technical things simply
• Comfortable learning software quickly and navigating multiple tools
• Organized and reliable, able to manage a queue and prioritize effectively

Nice to Have

• Familiarity with POS systems, e-commerce platforms, or SaaS support tools
• Experience with hardware troubleshooting (printers, card readers, networking basics)
• Exposure to support platforms like Zendesk, Intercom, or HubSpot