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VP Omni-Channel Retail Technology

lesschwab · Bend, OR · United States · On-site

Posted Aug 7, 2026

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Job Description: POSITION SUMMARY:   This executive will lead the technology strategy, product vision, and delivery of the platforms that power the end-to-end retail journey—from digital engagement and e-commerce through store operations, point-of-sale, customer loyalty, workforce enablement, and emerging omnichannel capabilities. This role will partner dynamically and cross-functionally with senior business leaders to scale the enterprise from more than 600 locations today to over 1,000 in the coming years. The ideal candidate thinks first as a customer advocate, second as an operator, and third as a technologist. They are obsessed with understanding customer and associate needs, identifying friction in the experience, and leveraging technology to create simple, scalable, and differentiated solutions. The successful candidate will possess a rare combination of customer-centric thinking, operational discipline, business acumen, and technology leadership. They will be expected to build and lead high-performing teams, and drive measurable business outcomes including, for example, improved customer conversion, and targeted returns on investments. PRIMARY RESPONSIBILITIES/FUNCTIONS Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions/primary responsibilities. Enterprise Leadership & Operating Model Co-Authorship Partner Retail Operations leadership to redefine cross-functional collaboration, establish shared KPIs, and eliminate IT/Operations silos. Own the comprehensive business case and capital allocation for major retail technology investments, translating tech spend directly into measurable P&L outcomes. Drive enterprise prioritization and collaborate with change leadership to ensure major technology rollouts include strict field readiness, communication, and store-level training loops. Customer & Store Associate Experience Optimization Drive seamless omnichannel experiences spanning e-commerce, mobile applications, customer communications, and loyalty/CRM platforms. Execute operational excellence by optimizing store associate micro-workflows, reducing transaction steps, and eliminating front-line system friction. Align on and meet operational service level targets spanning stability, performance, support, and scalability.   Omnichannel Product Strategy & Experimentation Establish a structured "sandbox" framework to safely pilot emerging technologies (e.g., automation, AI capabilities) in select stores using a fast-fail approach before enterprise scaling. Transition technology teams from a feature-delivery mindset to a data-driven mindset, ensuring clear definitions of operational ROI. Technology Delivery, Vendor Governance & Talent Development Lead high-performing engineering, product management, and support teams to deliver reliable, secure, and highly scalable enterprise platforms. Shape the external vendor ecosystem,…