[Hiring] Enterprise Customer Enablement Specialist @Scotch

Role Description

As an Enterprise Customer Onboarding Specialist, you'll lead complex, multi-location implementations of Scotch's POS platform for our largest customers. 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.

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

• 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.
• 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.