Senior Customer Onboarding Specialist

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

As a Senior Customer Onboarding Specialist at Scotch, you'll own the end-to-end onboarding experience for new customers, serving as their primary point of contact from contract signing through successful go-live. You'll be responsible for ensuring every implementation is organized, executed on time, and delivers an exceptional customer experience.

This is a highly customer-facing, hands-on role that requires a combination of technical expertise, project management, and outstanding customer service. You'll manage multiple implementations simultaneously, coordinating everything from hardware setup and software configuration to customer training, troubleshooting, and go-live support.

We're looking for someone who takes complete ownership of their work, anticipates customer needs, and follows through on every commitment. You should be exceptionally organized, detail-oriented, and proactive in your communication. Customers should never have to wonder what's happening next, chase down an update, or question whether something is being handled.

Success in this role requires flexibility, urgency, and a willingness to go above and beyond for our customers. That includes traveling to customer locations, adapting to their operating schedules, and occasionally working outside traditional business hours to ensure a successful implementation. We need someone who understands that onboarding sets the tone for the entire customer relationship and takes pride in getting every detail right.

Key Responsibilities

• Own the end-to-end customer onboarding experience, serving as the primary point of contact from contract signing through successful go-live.
• Deliver exceptional customer service through proactive, timely communication, clear expectation-setting, and consistent follow-through on customer commitments.
• Independently manage multiple implementations simultaneously, maintaining detailed project plans, timelines, milestones, action items, and customer documentation.
• Anticipate customer needs, identify potential roadblocks, and proactively resolve issues to keep implementations on track and ensure a seamless customer experience.
• Configure and deploy Scotch's POS platform, including payments, inventory management, reporting, and related operational workflows.
• Coordinate and execute hardware installations, including POS terminals, receipt printers, barcode scanners, payment devices, and cash drawers.
• Lead remote and on-site customer training, ensuring store owners, managers, and employees are confident using Scotch's platform.
• Troubleshoot technical and operational challenges, taking ownership of issues through resolution and escalating appropriately when additional support is needed.
• Partner closely with Sales, Support, Product, and Engineering to coordinate implementation requirements, resolve dependencies, and ensure seamless customer handoffs.
• Ensure implementation readiness and successful go-live by validating hardware, software configurations, customer training, and outstanding requirements.
• Travel to customer locations as needed, demonstrating flexibility to accommodate customer schedules, including occasional evenings, weekends, and Sunday travel for installations.
• Identify opportunities to improve onboarding processes, documentation, and training resources to drive greater efficiency and customer satisfaction.

Qualifications & Skills

• 4+ years of experience in customer onboarding, software implementation, technical account management, or a similarly high-touch, customer-facing role, with demonstrated ownership of complex customer implementations.
• Exceptional customer service skills, with a proven ability to build trust, manage expectations, resolve concerns, and consistently deliver a positive customer experience.
• Outstanding organizational and project management skills, including the ability to independently manage multiple active implementations, competing priorities, deadlines, and customer commitments without sacrificing quality.
• Excellent written and verbal communication skills, with a strong emphasis on timely responses, proactive updates, clear expectation-setting, and consistent customer follow-through.
• Demonstrated ownership and accountability, with a track record of taking initiative, following through on commitments, and driving issues to resolution without requiring constant oversight.
• Exceptional attention to detail, with the ability to maintain accurate documentation, identify potential issues early, and ensure critical implementation steps are completed correctly.
• Strong technical aptitude and troubleshooting skills, with the ability to diagnose and resolve hardware, software, and operational challenges in live customer environments.
• Experience with POS systems, payments technology, retail operations, or other hardware/software implementations strongly preferred.
• Familiarity with POS hardware, including receipt printers, barcode scanners, payment terminals, and cash drawers, preferred.
• Ability to remain composed, professional, and solutions-oriented when navigating customer concerns, competing priorities, or time-sensitive implementation issues.
• Comfortable working independently in a fast-paced, evolving startup environment where priorities may shift and initiative is expected.
• Willingness and ability to travel regularly, including occasional overnight stays, weekend travel, and schedule adjustments to accommodate customer installations and go-live requirements.A customer-first mindset, strong work ethic, and genuine pride in delivering high-quality work and following through on every detail.

Compensation & Benefits 

• The anticipated base salary range for this position is $100,000 - $110,000. Individual offers are based on a variety of factors, including experience, skills, qualifications, and internal equity. 
• Competitive equity package
• Comprehensive medical, dental, and vision coverage
• Unlimited flexible PTO

Why Scotch?

• Build from the ground floor: Help shape onboarding processes and operational standards as we scale
• Make a direct impact: Play a critical role in the customer experience during a key stage of growth
• Work cross-functionally: Collaborate closely with Sales, Support, Product, and Engineering
• Grow with the company: Join a fast-growing team with significant long-term opportunity