Principal Enterprise Technology Program Manager

Les Schwab•Bend, OR

About The Position

Les Schwab Tire Centers is seeking an experienced Principal Enterprise Technology Program Manager to lead complex, high-impact technology initiatives. This senior-level individual contributor role works at the intersection of technology, business operations, and execution, partnering with executive leadership and influencing cross-functional teams across the organization. The first major initiative is Route 52, a $50M+ enterprise point-of-sale (POS) transformation spanning approximately 600 stores. The role leads the next phase of deployment, establishes operational discipline, strengthens vendor accountability, and supports successful implementation and adoption. After Route 52, the position will continue leading major enterprise technology programs that support technology and operational excellence at Les Schwab. The program manager owns strategy, planning, execution, deployment readiness, stabilization, and business adoption for enterprise initiatives. They align stakeholders and resources, oversee vendors and implementation partners, communicate with executives and steering committees, manage risks, and develop scalable governance and deployment practices. Success requires strategic leadership combined with hands-on problem-solving and execution.

Requirements

10+ years of experience leading complex enterprise technology programs, implementations, or large-scale deployments.
Demonstrated success managing multimillion-dollar technology initiatives involving multiple business functions, vendors, and stakeholders.
Experience leading technology deployments across multiple locations, business units, or geographically distributed operations.
Proven ability to manage complex programs through implementation, go-live, stabilization, and successful business adoption.
Strong executive communication skills, including experience presenting to and influencing senior leadership.
Demonstrated expertise in vendor management, performance accountability, risk mitigation, and program governance.
Ability to balance strategic leadership with hands-on problem-solving and execution.
Experience leading cross-functional teams and driving results without direct reporting authority.

Nice To Haves

Experience leading large-scale POS, ERP, retail technology, or enterprise systems implementations.
Background in multi-location retail, distribution, supply chain, or other operationally complex environments.
Experience managing enterprise programs with budgets of $50M+ or deployments spanning hundreds of locations.
Demonstrated success stabilizing, recovering, or accelerating complex technology implementations.
Experience working with systems integrators, software providers, hardware deployment partners, and consulting firms.
Background in enterprise transformation consulting or leading large-scale technology programs within a complex organization.

Responsibilities

Own the strategy, planning, execution, and successful delivery of large-scale enterprise technology initiatives.
Lead complex, multimillion-dollar programs from implementation through stabilization and business adoption.
Partner with executive leadership to align program priorities, resources, timelines, and business outcomes.
Identify risks, resolve obstacles, and make informed decisions to keep programs moving forward.
Establish and manage deployment strategies, operational readiness criteria, and performance metrics across distributed business locations.
Lead cross-functional teams through implementation, training, go-live, and post-launch stabilization.
Use data and operational insights to determine deployment readiness, manage rollout pace, and continuously improve execution.
Ensure technology solutions meet business needs while minimizing disruption to store operations and customer experience.
Build alignment across Information & Digital Services, Retail Operations, Finance, Training, Analytics, and other business functions.
Communicate program progress, risks, and recommendations to executive stakeholders and steering committees.
Lead through influence, establish accountability, and drive decisions across teams without direct reporting relationships.
Oversee major technology vendors, implementation partners, and consulting relationships.
Set expectations for vendor deliverables, service levels, timelines, and quality; monitor performance and drive corrective actions as needed.
Develop scalable governance, reporting, and deployment practices for future enterprise initiatives.
Champion continuous improvement and organizational readiness throughout technology transformations.
Take ownership of the next phase of the Route 52 POS transformation and establish transparent performance measures and a disciplined deployment approach.