Enterprise Customer Enablement Specialist

This is a fully remote position, open to applicants in Colorado.

📋 Description

• Take full ownership of the onboarding journey for enterprise clients, managing everything from the initial kickoff to the complete go-live across all locations.

• Develop and oversee implementation project plans, which encompass timelines, milestones, phased rollouts, and customer responsibilities.

• Set up and deploy POS software for multi-site environments, addressing aspects such as payments, inventory management, pricing, reporting, user permissions, and related workflows.

• Spearhead data migration from legacy systems, including product catalogs, inventory data, customer records, and pricing details.

• Coordinate integrations with customers' existing software, such as accounting, e-commerce, and loyalty platforms, collaborating closely with the Engineering team.

• Organize and manage hardware deployment across various stores, including touch terminals, receipt printers, barcode scanners, payment terminals, and cash drawers.

• Conduct remote and on-site training sessions for store personnel, managers, and corporate users, while also developing train-the-trainer programs for larger implementations.

• Act as the primary liaison for customer stakeholders throughout the onboarding process, holding regular status meetings to communicate progress, risks, and next steps.

• Proactively identify implementation risks, troubleshoot issues, and escalate technical challenges when necessary.

• Create and maintain enterprise onboarding playbooks, documentation, training resources, and process guides.

• Collaborate closely with Sales, Account Management, Support, Product, and Engineering teams, ensuring smooth transitions from Sales during kickoff and to Support or Account Management post go-live.

• Monitor implementation progress, milestone achievements, and readiness for go-live across multiple concurrent enterprise projects.

• Relay customer feedback and recurring challenges to help refine the product and enhance the enterprise onboarding experience.

⛳️ Requirements

• 4-5+ years of experience in customer onboarding, implementation, professional services, or a related customer-facing role, including at least 2 years working with enterprise or multi-location clients.

• Proven ability to manage intricate implementations involving multiple stakeholders, workstreams, and deadlines.

• Strong background in POS systems, retail technology, fintech products, or similar hardware/software implementations is highly preferred.

• Experience with data migration and system integrations is essential.

• Proficient in working with spreadsheets, data imports, and technical teams.

• Familiarity with POS hardware such as receipt printers, barcode scanners, payment terminals, and cash drawers.

• Excellent project management capabilities.

• Outstanding communication skills, with the ability to clearly articulate technical concepts and build trust with both frontline staff and senior leaders.

• Strong troubleshooting and problem-solving abilities, particularly in live customer settings.

• Capacity to manage multiple concurrent implementations while ensuring every customer stays informed and on schedule.

• Comfortable working independently in a fast-paced startup atmosphere.

• Willingness to travel for on-site deployments and training sessions (approximately X%).

• Detail-oriented, demonstrating a strong sense of ownership and follow-through.

• Experience in the beverage alcohol retail sector or other regulated retail environments is a plus.

• Familiarity with customer platforms such as Intercom, HubSpot, or similar tools.

• Background in liquor retail, beverage distribution, or independent retail more broadly.

• Understanding of payment processing concepts (auth, capture, settlement, chargebacks).

🏝️ Benefits

• Competitive equity package within a VC-backed company (VMG, First Round, Lerer Hippeau).

• Coverage for medical, dental, and vision needs.

• 401(k) retirement plan.

• Flexible paid time off (PTO).

• Opportunity to develop systems, processes, and operational standards that will scale with the business.

• Influence the customer experience and directly impact product quality.

• Join a rapidly growing business with significant long-term opportunities.