IT Director, Retail Technology

Overview

Cavender's, the leading retailer in the Western and workwear industry, is seeking an experienced and strategic IT Director, Retail Technology to lead the vision, delivery, and optimization of the company's retail and enterprise technology portfolio. Reporting to the Chief Information Officer, this role is responsible for technology solutions that support store operations, omnichannel commerce, customer engagement, supply chain execution, and enterprise business processes, including Microsoft Dynamics 365 Finance & Operations, Point of Sale systems, payment technologies, loyalty platforms, and critical business integrations. The IT Director, Retail Technology partners closely with executive leadership, business stakeholders, technology vendors, and managed service providers to align technology investments with organizational objectives, drive digital transformation initiatives, improve operational efficiency, enhance the customer experience, and ensure reliable, scalable technology solutions that support Cavender's continued growth.

Duties and Responsibilities

Retail Technology & Store Operations

• Own all technology supporting retail store operations including Point of Sale (POS), payment terminals, back-office systems, inventory management, receiving, fulfillment, and store productivity solutions.
• Develop technology roadmaps that improve store associate efficiency and enhance the customer experience.
• Lead new store technology deployments, hardware refresh initiatives, and retail technology modernization efforts.

Warehouse Management Systems & Distribution Operations

• Provide leadership for warehouse management systems and related technologies supporting distribution center operations, including inventory control, receiving, replenishment, picking, packing, shipping, returns, and cycle counting.
• Partner with Supply Chain, Distribution Center leadership, Store Operations, eCommerce, and Finance teams to align warehouse technology capabilities with operational goals, fulfillment needs, and business growth.
• Oversee integrations between warehouse management systems, Microsoft Dynamics 365 Finance & Operations, eCommerce platforms, order management systems, parcel carriers, inventory systems, and reporting platforms.
• Drive technology initiatives that improve inventory accuracy, fulfillment speed, labor efficiency, shipment visibility, exception management, and overall distribution center performance.

Omnichannel Commerce & Customer Experience

• Partner with eCommerce and Marketing teams to support omnichannel customer journeys.
• Oversee integrations between eCommerce platforms, order management systems, loyalty solutions, customer engagement platforms, and enterprise applications.
• Drive initiatives that improve customer acquisition, retention, loyalty, and digital engagement.

Payments & Financial Technology

• Lead payment technology strategy including card processing, payment terminals, digital wallets, Buy Now Pay Later solutions, gift card platforms, and payment security.
• Lead fraud prevention and payment security initiatives, partnering with Finance, Loss Prevention, and third-party providers to identify emerging risks, implement controls, reduce fraud exposure, and protect both company assets and customer transactions across all sales channels.
• Partner with Finance to optimize payment processing costs and improve customer payment experiences.

Enterprise Applications & Business Systems

• Provide leadership for enterprise business applications supporting Retail, Supply Chain, Distribution, Finance, Customer Service, and Corporate Operations.
• Establish application governance standards, release management processes, and technology roadmaps.

Vendor & Managed Services Governance

• Manage relationships with strategic technology vendors, implementation partners, and managed service providers.
• Establish service level expectations and accountability measures to ensure high-quality technology support and delivery.

Security, Compliance & IT Controls

• Partner with Information Security, Internal Audit, and Finance teams to ensure compliance with SOX, PCI, and internal control requirements.
• Oversee user access governance, segregation of duties reviews, change management processes, and application security controls.

Data & Business Process Optimization

• Lead continuous improvement initiatives focused on process automation, data quality, system performance, and operational efficiency.
• Drive data governance initiatives that improve reporting accuracy, business insights, and decision-making capabilities.

Qualifications and Requirements

• Bachelor's degree in Information Technology, Computer Science, or a related field.
• 10+ years of experience in IT, with at least 5 years in a leadership role.
• Demonstrated experience leading technology strategy, application delivery, and operational support within a retail, distribution, logistics, or omnichannel environment.
• Experience managing complex system integrations between enterprise applications, eCommerce platforms, third-party service providers, payment processors, logistics providers, and customer engagement solutions.
• Proven success leading digital transformation initiatives, business process optimization efforts, and large-scale technology implementations.
• Experience developing and executing technology roadmaps aligned with business objectives and organizational growth strategies.
• Strong understanding of retail operations, inventory management, supply chain processes, customer experience technologies, and omnichannel commerce.
• Experience managing technology vendors, managed service providers, implementation partners, and strategic technology relationships.
• Knowledge of IT governance, security controls, compliance requirements, disaster recovery planning, and risk management best practices.
• Proven ability to lead cross-functional teams, manage competing priorities, and deliver complex projects on time and within budget.
• Excellent communication, presentation, and stakeholder management skills, with the ability to translate technical concepts into business value for executive and operational audiences.
• Strong analytical, problem-solving, and decision-making skills with a focus on continuous improvement and operational excellence.

Technical Skills

• Understanding of retail POS architecture, store systems, payment terminals, receipt printers, scanners, cash drawers, mobile devices, back-office systems, and store network dependencies.
• Experience with payment technologies, including payment gateways, processors, card-present and card-not-present transactions, tokenization, digital wallets, gift cards, fraud tools, chargebacks, reconciliation, and PCI compliance.
• Experience with system integration methods, including APIs, middleware, EDI, batch processing, file-based integrations, event-driven integrations, web services, and third-party connectors.
• Familiarity with Microsoft Azure, cloud-hosted applications, identity management, monitoring, application environments, and cloud integration concepts.
• Experience with SQL, relational databases, reporting tools, data validation, data mapping, and troubleshooting data issues across enterprise applications.
• Knowledge of application lifecycle management, including requirements gathering, solution design, configuration, development coordination, testing, deployment, release management, and support transition.
• Familiarity with IT service management tools and practices, including incident management, problem management, change management, request management, knowledge management, and service level reporting.
• Experience with project management and delivery tools, such as Jira, Azure DevOps, Microsoft Project, Smartsheet, ServiceNow, or similar platforms.
• Ability to troubleshoot complex business and technical issues across applications, integrations, data flows, vendors, infrastructure, and operational processes.
• Strong understanding of security and access controls, including role-based access, segregation of duties, audit logging, privileged access, and application security governance.
• Familiarity with retail analytics, reporting, master data, inventory data, sales data, customer data, and operational dashboards.
• Ability to evaluate technical designs, vendor proposals, architecture decisions, support models, and technology roadmaps

Preferred Skills

• Expertise in Microsoft Dynamics 365 Finance & Operations, particularly in Commerce and Supply Chain Management modules, and CE modules, particularly Sales Professional and Contact Center.
• Knowledge of project management, service management, and software delivery methodologies, including Agile, Waterfall, ITIL, and change management best practices.
• Experience using industry accepted project management tools.

Cavender's is an Equal Opportunity Employer. We do not discriminate based on race, religion, color, military status, national origin, sex, ancestry, age, sexual orientation, pregnancy, disability, genetic information, or any other personal characteristic protected under federal, state, or local law.

Cavender's will provide reasonable accommodations for persons with a disability upon request. If you have a disability and need assistance completing the application, please call Customer Service at View phone number on click.appcast.io or visit your nearest Cavender's store.

Equal Opportunity Employer
This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights notice from the Department of Labor.