Role Overview:
We are seeking a Director of Technology to lead the execution, integration, and performance of our digital systems across e-commerce, operations, and customer experience. Reporting to the VP of Operations, this role is responsible for ensuring that our technology stack directly supports frontline business execution, improves customer journey, and enables operational excellence across our portfolio of wine commerce brands.
We operate as an established startup: fast-paced, resourceful, and constantly evolving. We’re looking for someone who is scrappy, execution-oriented, and ready to roll up their sleeves-equally comfortable managing third-party developers and jumping in to troubleshoot a technical issue firsthand. You should be a builder, a problem solver, and a doer who thrives on momentum and thrives in environments where the blueprint is still being written. The ideal candidate brings deep technical fluency, systems thinking, and a strong service mindset to help us scale with speed and reliability.

Key Responsibilities:
System Ownership & Integration:
•  Oversee performance, configuration, and integration of all core platforms including Shopify Plus, Linnworks, Klaviyo, DropDay, Recharge, Figure, NetSuite, and internal tools
•  Ensure seamless front- and back-end connections between ecommerce systems, fulfillment tools, customer service platforms, and marketing infrastructure
•  Lead execution and QA of all system migrations and upgrades, including current Shopify transitions across multiple brands
Operational & Technical Execution:
•  Translate frontline pain points from Ops, Customer Service, and Fulfillment into scalable, supportable digital solutions
•  Maintain system stability, uptime, and support-ensuring daily operations are not disrupted by tech issues
•  Partner with internal teams to prioritize and execute high-impact technical improvements

Tooling & Automation:
•  Drive the development or configuration of tools for order merging, cubing, inventory allocation, and operational reporting
•  Identify and resolve bottlenecks in daily workflows through smart automation and integrations
Leadership & Collaboration:
•  Manage and direct work of external engineering vendors and internal Ecomm admin support staff
•  Provide structured documentation, release plans, and cross-training for internal tech enablement
•  Serve as primary technical partner to stakeholders across Operations, Customer Service, Marketing, and Finance
Data & Support Ownership:
•  Create visibility into key performance metrics and system usage
•  Ensure the business has access to timely, reliable, and actionable data across systems
•  Own triage and resolution of technical issues affecting customer experience or operational flow
Qualifications:
•  6+ years of experience leading technology or systems execution in a commerce or operations-driven environment at the Director level preferred.
•  Deep familiarity with Shopify Plus, ecommerce APIs, inventory systems (Linnworks or similar), and fulfillment logic
•  Bachelor’s degree required, technical Master’s Preferred.
•  Demonstrated success in implementing process improvements through technology
•  Strong communication skills with ability to translate technical concepts for non-technical stakeholders
•  Experience managing third-party developers and internal tech teams
•  Analytical and systems-oriented; SQL literacy a plus
•  Highly collaborative, with a bias for action and ownership
•  Strong systems thinker; understands how technology, data, and operations interconnect to drive business outcomes

Work Environment:
•  This role is based on our Napa HQ (Lombard location) and Gateway locations and is expected to be on-site 4+ days/week to work closely with Operations and CX teams.
•  Reasonable accommodation may be provided for individuals with disabilities.
Equal Opportunity Employer:
We are an Equal Opportunity Employer. We value diversity and are committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or protected veteran status.
Benefits:
•  Competitive incentive structure including performance milestones and bonuses
•  Medical, dental, and vision insurance, HAS/FSA
•  401(k) with match
•  Paid time off, holidays, and wine purchase benefits
•  Professional development support
Compensation:
$115,000-$135,000 / Per Year