Chief Omnichannel Retail Technology & Platforms

What the Tech, Bend; Bend (OR); Hybrid; USD 180,000 - 270,000; Full time

Job summary

What the Tech, Bend? seeks an executive to lead Omni-Channel Retail Technology, shaping strategy and delivery of platforms powering the end-to-end retail journey—from digital engagement and e-commerce to store operations and loyalty programs.

You will partner with senior business leaders to scale the enterprise from 600 locations to over 1,000, build high-performing teams, and drive measurable ROI through customer-centric, data-driven technology leadership.

Qualifications

• 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 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: translate technical concepts into financial terms for executives.

Responsibilities

• Lead the technology strategy, product vision, and delivery of platforms powering the end-to-end retail journey across digital and store operations.
• Partner with senior business leaders to scale the enterprise from 600 locations to over 1,000 in coming years.
• Build and lead high-performing teams and drive measurable business outcomes including improved customer conversion and ROI.
• Drive omnichannel experiences spanning e-commerce, mobile apps, loyalty/CRM, and workforce enablement.
• Establish sandbox framework to pilot emerging technologies in select stores before enterprise scaling.
• Mentor leaders, shape vendor governance, and ensure talent development across the IT organization.

Skills

Leadership

Retail tech

Omnichannel

Product management

Agile delivery

Data-driven decision making

Financial acumen

Job description

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

How You Will Contribute
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.

What will you do
In this role, the VP Omni-Channel Retail Technology will:

Enterprise Leadership & Operating Model Co-Authorship
● 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

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, 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

Skills & Qualifications
Educational/Experience 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

Required Technical Skills/Knowledge
● 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

General Knowledge and Abilities
● 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

Location, Compensation and Benefits
● Bend, OR
● Full time