Enterprise 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 founders came from Skupos (acquired 2023) and Drizly (acquired by Uber). We've raised $28M from VMG Partners, First Round, Lerer Hippeau, Watchfire, and Toba Capital, with angels including the founder of Drizly and early Toast executives, and in 2026 closed a $20M Series A. Forbes has recognized Scotch as a leader in liquor retail tech. 

Position Overview

As an Enterprise Customer Onboarding Specialist, you'll lead complex, multi-location implementations of Scotch's POS platform for our largest customers. You'll take each one from kickoff and data migration through hardware rollout, training, and go-live across every store. Your work will help enterprise retailers adopt the platform at scale and run it confidently across their business.

This is a high-impact, customer-facing role that combines project management, technical problem-solving, and relationship management. You'll work with stakeholders at every level of a customer's organization, from store managers to operations, IT, and finance leaders. Internally, you'll coordinate closely with our own teams so that every enterprise rollout is well planned, on schedule, and set up for long-term success.

Key Responsibilities 

• Own the end-to-end onboarding experience for enterprise customers, from kickoff through full go-live across all locations
• Build and manage implementation project plans, including timelines, milestones, phased or location-by-location rollouts, and customer-side responsibilities
• Configure and deploy POS software for multi-location environments, including payments, inventory management, pricing, reporting, user permissions, and related workflows
• Lead data migration from legacy systems, including product catalogs, inventory, customer records, and pricing
• Coordinate integrations with customers' existing systems, such as accounting, e-commerce, and loyalty platforms, in partnership with Engineering
• Plan and coordinate hardware deployment across multiple stores, including touch terminals, receipt printers, barcode scanners, payment terminals, and cash drawers
• Lead remote and on-site trainings for store staff, managers, and corporate users, and build train-the-trainer programs for larger rollouts
• Serve as the primary point of contact for customer stakeholders during onboarding, run regular status meetings, and communicate progress, risks, and next steps
• Identify implementation risks early, troubleshoot issues, and escalate technical problems when needed
• Build and maintain enterprise onboarding playbooks, documentation, training materials, and process guides
• Partner closely with Sales, Account Management, Support, Product, and Engineering, including smooth handoffs from Sales at kickoff and to Support or Account Management after go-live
• Track implementation progress, milestone completion, and go-live readiness across concurrent enterprise projects
• Share customer feedback and recurring pain points to help shape the product and improve the enterprise onboarding experience

Qualifications & Skills

• 4-5+ years of experience in customer onboarding, implementation, professional services, or a similar customer-facing role, including at least 2 years supporting enterprise or multi-location customers
• Proven track record managing complex implementations with multiple stakeholders, workstreams, and deadlines
• Experience with POS systems, retail technology, fintech products, or other hardware/software implementations strongly preferred
• Experience with data migration and system integrations, and comfort working with spreadsheets, data imports, and technical teams
• Familiarity with POS hardware such as receipt printers, barcode scanners, payment terminals, and cash drawers
• Strong project management skills; experience with project management tools and structured implementation methodologies a plus
• Excellent communication skills, with the ability to explain technical concepts clearly and to build credibility with both frontline staff and senior leaders
• Strong troubleshooting and problem-solving skills, especially in live customer environments
• Ability to manage multiple concurrent implementations while keeping every customer informed and on track
• Comfortable working independently in a fast-paced startup environment
• Willingness to travel for on-site deployments and trainings (approximately X%)
• Detail-oriented, with a strong sense of ownership and follow-through
• Experience in beverage alcohol retail or other regulated retail environments a plus

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 $110,000-$120,000. 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
• Flexible PTO

Why Scotch?

• Build from the ground floor: Create systems, processes, and operational standards that will scale with the business
• 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