Role Overview

We are seeking a Customer Support & Systems Operations Associate to take ownership of client-facing support, onboarding, and operational system management for our application and its integrations.

This role sits at the intersection of customer service, technical troubleshooting, and product operations. It requires an individual who is not only responsive to client needs, but also capable of diagnosing root causes, improving workflows, and contributing to system scalability over time.

The position will initially require hands-on, intensive onboarding and knowledge transfer, with the goal of transitioning ownership of day-to-day operations and enabling the product lead to focus on strategic development.

This is a Full-Time, salaried position with benefits. This is a hybrid role, with the candidate working from the office 2-3x/week. This position is currently slated to work from our Napa office. However, we are also open to considering candidates in either our San Francisco or New York instead.

Core Responsibilities

1. Customer Support & Troubleshooting

• Serve as the primary point of contact for client support issues across platforms (QuickBooks Desktop/Online and integrated systems)
• Diagnose issues, identify root causes, and resolve or escalate with clear documentation
• Reproduce bugs and communicate effectively with engineering or vendors
• Manage urgent issues, including data discrepancies and system failures

2. Client Onboarding & Training

• Schedule & perform product demos for for prospective clients upon request
• Manage full onboarding lifecycle: scheduling, setup, configuration, and training
• Guide clients through adoption and early-stage usage
• Create scalable onboarding processes and materials

3. Systems & Subscription Operations

• Monitor new accounts, subscriptions, renewals, and failed payments
• Ensure continuity of service and operational accuracy
• Identify opportunities for automation and process improvement

4. Documentation & Knowledge Management

• Build and maintain centralized documentation:
• Installation guides
• Troubleshooting workflows
• Internal system notes
• Convert tribal knowledge into structured, accessible resources
• Create instructional content (including video tutorials)

5. QA, Testing & Release Support

• Test new features and integrations
• Validate system behavior across platforms (e.g., WineDirect, Commerce7, eCellar, etc.)
• Support bug tracking and release processes

6. Product & Systems Improvement (Secondary, Growth Area)

• Identify workflow gaps and inefficiencies
• Provide feedback on product improvements
• Develop a working understanding of system capabilities and constraints

Candidate Profile

Experience Requirements

• 2+years in a role combining:
• Customer support / client success
• Technical support / systems operations
• Experience working with SaaS platforms or integrations strongly preferred
• Exposure to accounting software (e.g., QuickBooks) highly desirable

Core Competencies

1. Technical & Systems Aptitude

• Highly PC-savvy:
• Comfortable managing file systems and software installations
• Able to navigate multiple platforms and environments
• Experience with:
• CRM systems
• Email marketing tools
• Familiarity with winery e-commerce systems desirable
• Ability to learn new systems quickly and independently

2. Troubleshooting & Analytical Thinking

• Strong problem-solving mindset
• Naturally curious—seeks to understand why issues occur, not just fix them
• Able to research, test, and validate solutions methodically

3. Organization & Process Orientation

• Strong ability to create and maintain structured systems
• Detail-oriented with disciplined documentation habits
• Comfortable managing multiple workflows simultaneously

4. Customer Service Orientation

• Patient, clear, and professional in client interactions
• Able to translate technical concepts into understandable guidance
• Experience supporting non-technical users

5. Communication & Training Ability

• Able to create clear written documentation
• Comfortable producing instructional videos and training materials
• Strong internal communication with technical and non-technical stakeholders

6. Business & Accounting Awareness

• Basic understanding of accounting principles
• Familiarity with how accountants think and operate (especially within QuickBooks environments)
• Ability to contextualize issues within financial workflows

7. Emerging Business Analyst Mindset

• Interest in understanding systems at a deeper level
• Ability to connect operational issues to broader product or process improvements
• Potential to grow into a more strategic systems/product role

What We Offer

• Opportunities for Advancement: We are growing within all of our categories every year, affording every employee potential for promotion and career advancement.
• Fun: Happy hours, events, product tastings both in the office and outside.
• Diversity: We strongly believe the diversity of our staff – made up at all levels of people from all backgrounds, from 12 countries, speaking 8 languages – is our strength, not only because of the vibrant intellectual and cultural working environment such diversity fosters but because it reflects the diversity of the marketplace in which we make our appeal and the diversity of our clients.
• Work-life balance and generous PTO: We believe employees who are happier outside of work are happier at work, and vice versa, so we have created a culture that prioritizes work-life balance. We have a flexible PTO system and we take off the week between Christmas and New Year's.
• Expertise: We are the largest fine wine and spirits-focused integrated communications agency in the U.S.
• Pay & Benefits: We offer competitive salaries within our category and full benefits - health, dental, vision, life insurance, 401K, and a generous PTO policy.