Head of Technology

About the Role

True Classic is hiring a Head of Technology to take ownership of the company’s enterprise technology strategy, systems, integrations, data infrastructure, security, business intelligence, and artificial intelligence capabilities. In this position, you will lead the entire technology function, ensuring True Classic operates through a connected, secure, scalable, and intelligent technology ecosystem across the entire organization. Reporting directly to the CEO, you will define the future of True Classic’s technology stack while ensuring the systems supporting the business today remain reliable, accurate, and effective.

We are looking for a hands-on, strategic, AI-native, and business-minded technology leader with a proven ability to build technical teams, modernize enterprise systems, scale data capabilities, automate business processes, and translate complex business needs into practical technology solutions in a fast-paced, dynamic environment.

All True Classic roles are global and omni-channel, encompassing responsibilities across all product categories, geographies, and sales and marketing channels. This role will have significant influence over DTC, retail, wholesale, marketplaces, and emerging channels, ensuring strategic alignment and operational excellence enterprise-wide.

Areas of Accountability

Technology Leadership and Strategy

• Lead True Classic’s technical teams, including NetSuite developers, Shopify developers, AI developers, data engineers, data transformation specialists, and business intelligence professionals.
• Define and own the long-term vision, architecture, and roadmap for the entire True Classic technology stack.
• Establish a disciplined build-versus-buy framework, determining when to implement leading external platforms and when to develop proprietary solutions.
• Lead technology vendor selection, contract negotiations, renewals, and performance management, ensuring every platform delivers measurable business value.

Enterprise Systems, Integrations, and Corporate IT

• Own the enterprise systems that operate the company, beginning with NetSuite and the platforms supporting finance, operations, inventory, fulfillment, commerce, and reporting.
• Oversee integrations, middleware, APIs, and data flows between systems, ensuring information moves accurately and reliably throughout the organization.
• Lead corporate IT operations, including employee provisioning, identity and access management, devices, technical support, and onboarding and offboarding processes.
• Maintain a clean, documented, governed, and scalable technology environment that allows the organization to move quickly without sacrificing reliability or control.

Data Governance, Security, Warehousing, and Business Intelligence

• Establish enterprise-wide standards for data ownership, definitions, quality, access, protection, documentation, and governance.
• Own True Classic’s security posture, including access controls, vendor risk, compliance, data protection, and the security of customer, employee, and company information.
• Lead the data platform end to end, encompassing data engineering, transformation, warehousing, semantic layers, reporting, and business intelligence.
• Create a trusted, accessible source of truth that enables teams across the company to make timely decisions based on accurate data rather than assumptions.

AI and the Application Intelligence Layer

• Lead True Classic’s AI function and establish the strategy for applying artificial intelligence across the organization.
• Develop context layers, intelligent agents, automations, and custom applications that simplify workflows and perform meaningful business work.
• Partner with every function to identify opportunities where AI can improve speed, quality, efficiency, decision-making, or cost.
• Build and scale proprietary solutions when existing vendors cannot adequately address True Classic’s business requirements.

Cross-Functional Collaboration

• Partner with Finance and Operations to ensure NetSuite and related enterprise systems support accurate financial reporting, inventory management, operational planning, and scalable business processes.
• Work with DTC, retail, wholesale, marketplace, supply chain, and international teams to ensure systems and integrations support upstream and downstream operational requirements.
• Collaborate with executive leadership and functional leaders to prioritize technology investments based on business impact, organizational needs, and long-term strategy.
• Partner with People, Legal, and Finance to maintain effective access controls, security practices, vendor governance, employee technology processes, and compliance standards.

Qualifications

• 10+ years of progressive experience in technology leadership, enterprise systems, software engineering, data, business intelligence, or a related field.
• Experience leading multidisciplinary technical teams across software development, enterprise systems, data engineering, analytics, artificial intelligence, and corporate IT.
• Proficiency with enterprise and commerce platforms such as NetSuite, Shopify, data warehouses, business intelligence tools, integration platforms, APIs, cloud environments, and SaaS applications.
• Strong technical, analytical, operational, strategic planning, and commercial negotiation skills.
• Demonstrated ability to translate business problems into scalable technology solutions and measurable business outcomes.
• Proven ability to evaluate architecture, lead platform implementations, manage integrations, and make sound build-versus-buy decisions.
• Track record of success working cross-functionally, managing complex technology environments, and scaling systems within a rapidly growing organization.
• Demonstrated understanding of cybersecurity, access management, data governance, vendor risk, compliance, and enterprise technology controls.
• Experience developing or implementing AI-powered applications, workflow automations, intelligent agents, or context-aware systems.

Preferred Qualifications

• Experience supporting a global, omni-channel consumer, apparel, retail, or e-commerce business.
• Hands-on experience with NetSuite development, administration, architecture, or major ERP implementations.
• Experience with Shopify and the broader technology ecosystem supporting digital commerce and customer experiences.
• Strong understanding of modern data architecture, data transformation, warehousing, semantic models, and self-service business intelligence.
• Ability to evaluate emerging technologies without chasing unnecessary tools or introducing avoidable complexity.
• Demonstrated ability to simplify technology environments, consolidate platforms, reduce manual work, and improve operating efficiency.
• Experience negotiating major technology contracts, managing vendor relationships, and implementing zero-based reviews of software spending.
• Ability to move quickly while maintaining strong standards for data accuracy, documentation, system reliability, and security.

Compensation and Benefits

• Competitive salary + performance bonus
• 401(k) plan with 3% company match
• Unlimited PTO and sick time
• Company-paid medical, dental, and vision insurance
• $100/month Health & Wellness stipend
• Free Employee Assistance Program (EAP)
• $100/month Personal Workspace/Office stipend
• $1,000/year True Classic merchandise allowance