Point of Sale (POS) Installation Technician

About the role

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 founding team includes leaders from Skupos (acquired in 2023), Drizly (acquired by Uber ), and engineering leaders from top technology companies. We've raised $28M from VMG, First Round, Lerer Hippeau, Watchfire, and Toba Capital, alongside angels including the founder of Drizly and early executives from Toast . Forbes has recognized Scotch as a leader in the liquor retail technology space. 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.

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 under deadline pressure.
• Clear, professional communication skills for working with store personnel and remote teams.
• High school diploma or equivalent.
• Based in or willing to relocate to Denver, Nashville, Atlanta, NYC or Boston.
• Valid driver's license and clean driving record.
• Ability to travel by air and rent vehicles
• Ability to lift, carry, and position equipment up to 50 lbs.
• Extended periods of standing, walking, bending, kneeling, crouching, and reaching during installations.
• Compensation & Benefits
• Starting at $70,000 per year, with flexibility depending on experience
• Competitive equity package
• Comprehensive medical, dental, and vision coverage
• Unlimited flexible PTO
• Why Scotch?
• Solve meaningful technical problems: Work directly on issues that impact real-world business operations
• Collaborate closely with Engineering: Help influence product quality and operational improvements
• Gro

Benefits

Additional Information

Location: Remote / Field-based - Continental US | Travel: Up to 100% | Employment Type: Full-time

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