Retail Technology Associate Jobs in Kentucky (NOW HIRING)

VP Omni-Channel Retail Technology
Location: Bend, OR
Employment Type: Full time
Job Requisition ID: R-14875
Experience: 15+ years of progressive leadership experience managing large-scale retail technology, digital, or omnichannel portfolios

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.

• Partner with 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

• 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

• Bilingual Leadership Capabilities: 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

• Bend, OR
• Full time