Onboarding Specialist

Scotch•Quinte West, ON

6d•$75,000 - $85,000•Hybrid

About The Position

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. As an Onboarding Specialist, you’ll guide new customers through the implementation of Scotch’s POS platform — from hardware setup and software configuration to training and go-live support. You’ll play a critical role in helping customers successfully adopt the platform and feel confident using it in their day-to-day operations. This is a high-impact, customer-facing role that combines technical troubleshooting, project coordination, and relationship management. You’ll work closely with customers and internal teams to ensure every implementation is smooth, organized, and set up for long-term success.

Requirements

2+ years of experience in customer onboarding, implementation, technical support, or a similar customer-facing operational role
Experience working with POS systems, fintech products, or other hardware/software implementations preferred
Familiarity with POS hardware such as receipt printers, barcode scanners, payment terminals, and cash drawers
Strong troubleshooting and problem-solving skills, especially in live customer environments
Excellent communication skills with the ability to explain technical concepts clearly and simply
Strong organizational skills and ability to manage multiple implementations simultaneously
Comfortable working independently in a fast-paced startup environment
Detail-oriented with a strong sense of ownership and follow-through

Responsibilities

Own the end-to-end onboarding experience for new customers, ensuring a smooth transition onto the Scotch platform
Configure and deploy POS software, including payments, inventory management, reporting, and related workflows
Coordinate and support hardware setup, including touch terminals, receipt printers, barcode scanners, and cash drawers
Lead remote and occasional on-site customer trainings to ensure users are comfortable and confident using the system
Serve as the primary point of contact during onboarding, proactively communicating timelines, next steps, and issue resolution
Troubleshoot implementation issues and escalate technical problems when needed
Build and maintain onboarding documentation, training materials, FAQs, and process guides
Partner closely with Sales, Support, Product, and Engineering teams to ensure a seamless customer experience
Track onboarding milestones, implementation progress, and customer readiness for go-live
Share customer feedback and recurring pain points to help improve the product and onboarding experience over time