Customer Enablement Specialist
Location: Denver, CO preferred // Remote (US) with occasional field travel
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 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
Skills Required
- 3+ years in a customer-facing training, onboarding, or support role
- Experience at a POS, payments, fintech, or retail SaaS company
- Strong written and verbal communication skills
- Patience and ability to explain technical concepts to non-technical users
- Comfort with chat-first support workflows (Intercom)
- Operational instincts to identify recurring issues and improve training materials
- Willingness to travel occasionally for in-person installs or training (estimated 5-10%)
- Experience with Intercom, HubSpot, or similar customer platforms
- Background in liquor retail, beverage distribution, or independent retail
- Familiarity with payments processing concepts (auth, capture, settlement, chargebacks)
What the Team is Saying
Scotch Compensation & Benefits Highlights
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Healthcare Strength — Health, dental, and vision insurance are consistently listed, with employer-subsidized premiums referenced in job materials. Feedback suggests the core medical coverage is solid for a small, venture‑backed startup.
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Equity Value & Accessibility — Employee equity is included across postings, providing ownership potential aligned with early‑stage growth. Feedback suggests this upside is a meaningful part of the total rewards mix.
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Leave & Time Off Breadth — An unlimited PTO policy is advertised across public materials. Feedback suggests flexibility is a notable feature, though actual usage norms should be confirmed during the offer process.
Scotch Insights
What We Do
From neighborhood stores to destination warehouses, liquor retailers of all sizes have been held back by manual tasks, slow systems and limited business intelligence. So we decided to build something better — smarter software that saves time and improves margins so independent retailers could focus on their customers, not manually managing inventory.
Why Work With Us
Company building is a team sport, and we aim to to win the World Championships. We’re looking for heat-seeking missiles that aspire to be the absolute best in their field, to constantly raise the bar amongst their peers, and to win. We’re a low-ego, high-outcome focused crew with a strict no asshole policy.
Scotch Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
We're a distributed remote team, with our headquarters in Denver, CO. We hire the best people we can find, regardless of location.
