Customer Enablement Specialist

About the role

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.

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

The anticipated base salary range for this position is $75,000-$85,000. Individual offers are based on a variety of factors, including experience, skills, qualifications, and internal equity.

• 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?

• Create systems, processes, and operational standards that will scale with the business
• Inherit an existing team while building new functions and capabilities
• Shape the customer experience and directly influence product quality
• Join a rapidly scaling business with significant long-term opportunity