Customer Enablement Specialist

Scotch • Quinte West, ON

2d • $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. The 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. We are the operating system for independent liquor retailers — point-of-sale, payments, back-office, and e-commerce, purpose-built for the three-tier alcohol distribution system, and we onboard 30-50 new stores a month. The first 21 days of a merchant's life on the platform determine whether they thrive on it long-term. That's why we're hiring a Customer Training Specialist to own that window. In this position, you will run live training sessions for new merchants, handle the Post-Install support inbox, and be the human face of Scotch POS during the period that matters most. This is a high-touch, customer-facing role on a team that is being purpose-built around merchant retention and product adoption in the formative window.

Requirements

• 3+ years in a customer-facing training, onboarding, or support role — ideally at a POS, payments, fintech, or retail SaaS company.
• Strong written and verbal communication. You can explain a credit card batch settlement to someone who has never thought about one.
• Patience. Our customers are smart business operators who are not always comfortable with software, and the job is meeting them where they are.
• Comfort with chat-first work. The majority of your daily volume comes through Intercom, not phone or email.
• Operational instincts. You notice when the same question keeps coming up and ask whether the training material needs to change.
• Willingness to occasionally travel for in-person installs or training sessions (estimate 5-10% travel).

Nice To Haves

• Experience with Intercom, HubSpot, or similar customer platforms.
• Background in liquor retail, beverage distribution, or independent retail more broadly.
• Familiarity with payments processing concepts (auth, capture, settlement, chargebacks).

Responsibilities

• Run live onboarding training sessions for new merchants — video calls, screen-shares, and the occasional in-person session at the store.
• Own the Post-Install inbox in Intercom, the dedicated support queue for customers in their first 21 days. Tight response SLAs, high-touch tone.
• Translate complex POS workflows into language an independent store owner actually understands. Most of our customers are not technical.
• Build and maintain training materials — short videos, written guides, in-product walkthroughs — that scale your knowledge so you are not the bottleneck.
• Flag at-risk merchants early. If a new customer is not getting traction, you are the first to know and the first to course correct.
• Partner closely with the broader support team to hand off cleanly when customers graduate from post-install to established status.
• Contribute to the product feedback loop — what is confusing for new merchants, what training they keep asking for, where the product needs to get clearer.

Benefits

• $85,000 base salary
• Competitive equity package in a VC-backed company (VMG, First Round, Lerer Hippeau)
• Medical, dental, and vision coverage + 401(k) plan
• Unlimited flexible PTO

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed