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 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.

Key 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.

Qualifications & Skills

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).

Compensation & 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

Why Scotch?

Build from the ground floor: Create systems, processes, and operational standards that will scale with the business
Lead a growing organization: Inherit an existing team while building new functions and capabilities
Drive meaningful impact: Shape the customer experience and directly influence product quality
Grow with the company: Join a rapidly scaling business with significant long-term opportunity

See more open positions at Scotch

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