VP Omni-Channel Retail Technology

Les Schwab•Bend, OR

19h•Hybrid

About The Position

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.

Requirements

15+ years of progressive leadership experience managing large-scale retail technology, digital, or omnichannel portfolios.
Proven track record of scaling technology organizations and architectures during periods of rapid, multi-location geographic growth (600+ locations).
Demonstrated success leading enterprise-scale digital transformation initiatives and modernizing legacy retail environments without creating operational discontinuity.
Deep functional knowledge of modern retail technology platforms, including Point of Sale (POS), customer journey orchestration, workforce enablement tools, inventory visibility systems, and CRM infrastructure.
Expert-level experience establishing contemporary product management, agile delivery, and customer-centered design disciplines within an engineering organization.
Exceptional ability to debate technical system architecture with engineers, and seamlessly translate those concepts into financial terms (gross margin, customer lifetime value) for executive and board-level discussions.
Strong business and financial acumen with an owner’s mindset; highly comfortable using data to challenge conventional thinking and influence cross-functional peers who do not report to them.
A "Design Thinking" practitioner who prioritizes empathy for the end-user.

Responsibilities

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.
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.
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.
Lead high-performing engineering, product management, and support teams to deliver reliable, secure, and highly scalable enterprise platforms.
Shape the external vendor ecosystem, determining when to build, buy, or partner, while managing risk and holding partners accountable to business outcomes.
Build leadership depth within the IT organization, actively mentoring future technical and product leaders to support long-term talent succession.