Point of Sale (POS) Installation Technician

Location: Remote / Field-based — Continental US | Travel: Up to 100% | Employment Type: Full-time About Us Scotch is building the next-generation operating system for beverage alcohol retailers — combining POS, payments, back office, and e-commerce into a platform purpose-built for liquor stores. We’re modernizing one of the oldest industries in the world: the $1.6T beverage alcohol market. Our platform helps retailers run more efficiently through streamlined payments, inventory management, reporting, and day-to-day operations. Our founders came from Skupos (acquired 2023) and Drizly (acquired by Uber). We've raised $28M from VMG Partners, First Round, Lerer Hippeau, Watchfire, and Toba Capital, with angels including the founder of Drizly and early Toast executives, and in 2026, closed a $20M Series A. Forbes has recognized Scotch as a leader in liquor retail tech. Position Overview We are seeking a hands-on, road-ready Point of Sale (POS) Installation Technician to deploy and configure POS systems in retail locations across the continental United States. This is a travel-intensive, field-based position: you will be on the road up to 100% of the time, moving between stores to install, test, and hand off complete POS environments. The ideal candidate is technically capable, physically energetic, comfortable with frequent travel non-standard hours, and dependable under deadline pressure. If you like variety, independence, seeing a new city every week, and the satisfaction of walking out of a store knowing everything is live and ready, this role is for you. Key Responsibilities Travel to retail locations throughout the continental US to install, configure, and commission POS hardware and software. Perform installations during pre-opening windows to ensure all systems are fully operational with limited disruption to business. Disassemble the previous POS system and organize components into boxes for the retailer to dispose of. Set up and connect Scotch POS terminals, cash drawers, receipt printers, barcode scanners, payment/card readers, customer-facing displays, and related peripherals. Run, route, and manage cabling; coordinate with on-site networking and electrical as needed to ensure proper connectivity. Install and update POS software, apply configurations, and verify integration with back-office, payment, and inventory systems. Test all hardware and software end-to-end, troubleshoot and resolve issues on-site, and confirm full functionality before sign-off. Provide basic orientation or training to store staff on the installed system when required. Complete installation checklists, documentation, and reporting accurately and on time. Communicate status, blockers, and completion to project managers, store contacts, and the deployment team. Maintain, transport, and account for tools, equipment, and inventory while traveling. Adhere to all safety, security, and brand standards while working on-site. Manage travel arrangements for all installations (hotel, flight, rental car, etc.) Qualifications & Skills 1+ years of experience installing, deploying, or supporting Point of Sale (POS) systems, retail technology, or similar field-based technology solutions. Experience performing onsite hardware installations, device configuration, cabling, testing, and go-live support in customer environments. Proven ability and willingness to travel up to 100% of the time throughout the continental US, including overnight stays and extended periods away from home. Comfortable with a highly variable schedule, frequent flights and long drives between markets, and being away from home for consecutive days at a time. Hands-on technical aptitude with hardware setup, cabling, and troubleshooting. Basic understanding of networking concepts (IP addressing, routers/switches, connectivity troubleshooting). Strong problem-solving skills and the ability to work independently with minimal supervision. Excellent reliability, time management, and follow-through…