Digital Associate Jobs in Bend, OR (NOW HIRING)

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, 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.

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.

Physical Requirements:

• Ability to sit, stand, and operate standard office equipment for extended periods.

• Ability to travel frequently to retail store locations, corporate offices, and field operations to observe customer and associate interactions firsthand.

Work Environment:

• Primary work performed within a professional corporate office environment.

• Requires regular field exposure within active retail store environments to audit technical performance and workflow execution.