Overnight Pos Installer Jobs (NOW HIRING)

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 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

• Compensation: The anticipated base salary range for this position is $70,000-$75,000. Individual offers are based on a variety of factors, including experience, skills, qualifications, and internal equity. 
• 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
• Grow your technical expertise: Gain hands-on experience across software, hardware, networking, and payments systems
• Join a fast-growing company: Be part of a team building modern infrastructure for a massive industry

How to Apply

Submit your application through this job posting & email brett.medina@scotchpos.com with subject line "POS Installation Technician".

In your email, please include: 

• A brief overview of your technical support or troubleshooting experience
• Any experience working with POS systems, Android devices, hardware support, or networking
• An example of a complex technical issue you diagnosed or resolved
• Why you're interested in Scotch and this role specifically

Scotch is an equal opportunity employer. We value diverse perspectives and are committed to creating an inclusive environment for all employees.