Senior Director IT Strategic Transformation

About The Role

Gap Inc. is seeking a Strategic Transformation Lead to drive two of its most consequential technology bets: the execution of its enterprise GCP Data and AI transformation, and the design and stand-up of an AI-native technology delivery entity built on the emerging agentic development toolchain.

This is a senior role for an executive-caliber operator who has done this before — someone who can anchor a complex, multi-year platform transformation while simultaneously helping Gap design what technology delivery looks like in an AI-native world. The two mandates are sequential in emphasis but parallel in mindset: get the data and AI foundation right and use that foundation to define and build the delivery model that runs on top of it.

GCP Data & AI Program Execution

The GCP Data and AI transformation is Gap’s foundational bet. A strong data and AI platform is the prerequisite for everything that follows — personalization at scale, agentic automation, AI-driven decision-making across brands and functions. This mandate is about making that bet pay off.

GCP Data & AI Program Execution Responsibilities

• Enterprise Transformation Strategy Translate Gap’s Data and AI vision into an executable multi-quarter transformation roadmap with clear sequencing, milestones, dependencies, and value measures tied to business outcomes — not technical deployments.
• Data & AI Program Leadership Drive integrated execution across platform modernization, analytics enablement, data operations, AI capabilities, and engineering delivery — across multiple teams, vendors, and strategic partners including our execution partners and Google.
• Executive Governance and Decision Support Serve as a trusted advisor to SVP and executive leadership on transformation progress, risk posture, tradeoffs, investment decisions, and sequencing — with the judgment to surface the hard things early.
• Operating Model and Organizational Effectiveness Help define and evolve the operating model required to scale Data and AI delivery across the enterprise.
• People & Culture Leadership Build, inspire, and develop a high-performing team that embodies accountability, collaboration, and innovation.
• Portfolio, Financial, and Resource Governance Contribute to annual and quarterly planning processes for the transformation portfolio, including sequencing, prioritization, funding alignment, and value realization.
• Risk, Readiness, and Execution Discipline Establish rigorous mechanisms for identifying, escalating, and resolving risks, dependencies, and execution bottlenecks.

AI-Driven Technology Delivery Responsibilities

• Structure and Operating Model Define the structure, operating model, and capability architecture of an AI-native technology delivery entity — one built from the ground up the broader agentic development toolchain; establish the overall AI operating model based on existing governance work, AI-native SDLC, toolchain governance, delivery standards, quality and security posture, and operating principles that make AI-driven delivery safe, repeatable, and measurable at scale.
• Talent and Resource Model Design the talent and resource model for an AI-native delivery shop — define roles, human-to-AI ratio across delivery contexts, and how the organization scales without linear headcount growth.
• Sequencing and Transition Map the path from Gap’s current technology delivery operating model to the AI-native target state, with clear milestones, decision points, toolchain adoption gates, and value realization markers; partner with key stakeholders to ensure alignment with existing investments.
• Governance and Quality Establish the governance model that ensures AI-driven delivery meets security, compliance, architecture, and quality standards, including review, testing, deployment, and monitoring of code generated by agents.
• Executive Investment Case Develop the executive narrative and investment case required to move from concept to commitment — operating model options, cost and productivity framing, risk considerations, and a clear phased recommendation.

Who You Are

Transformation and Strategic Leadership

• Proven success leading enterprise transformation programs in complex, matrixed organizations.
• Strong ability to connect strategic ambition to executable plans, governance structures, and measurable outcomes.
• Demonstrated ability to serve as a trusted advisor to senior executives during periods of change, modernization, or operating model evolution.
• Passionate about leading teams, developing people and creating a culture of ownership and continuous improvement.

Data, Technology, and Platform Fluency

• Strong technical fluency across modern cloud, data, platform, and enterprise technology environments.
• Working understanding of data platforms, AI and analytics enablement, cloud ecosystems (GCP preferred), security and compliance considerations, and modern software delivery practices.
• Familiarity with AI-native development toolchains and agentic SDLC frameworks.
• Ability to engage credibly with engineering, architecture, infrastructure, and product leaders on technical tradeoffs and execution implications.

Program and Portfolio Delivery Excellence

• Deep experience running large, cross-functional programs with multiple workstreams, interdependencies, and executive stakeholders.
• Strong command of portfolio planning, milestone management, risk governance, capacity alignment, and delivery reporting.
• Track record of improving execution predictability, organizational transparency, and operational discipline.

Executive Communication and Influence

• Exceptional communication skills with the ability to distill complexity into clear, concise, decision-oriented narratives.
• Strong executive presence and credibility with senior business and technology stakeholders.
• Ability to unify divergent points of view, surface options and tradeoffs, and drive alignment without relying solely on direct authority.

Financial and Operational Acumen

• Experience managing portfolio budgets, capital and operating planning, investment prioritization, and value realization.
• Strong analytical orientation with the ability to use data to guide decisions, manage tradeoffs, and improve outcomes.
• Comfortable operating at both strategic and operational levels simultaneously.

Operating Model and Organizational Design

• Strong capability in operating model design, organizational effectiveness, and stakeholder orchestration.
• Experience standing up new organizational entities, AI centers of excellence, or capability organizations in enterprise environments.
• Demonstrated ability to sustain momentum through ambiguity, competing priorities, and enterprise complexity.

Preferred Additional Experience

• 15+ years of leadership experience spanning enterprise transformation, program leadership, technology strategy, or engineering and data operations.
• Experience leading large-scale GCP, data, analytics, platform, or AI-related transformations — retail, consumer, or digital environments strongly preferred.
• Experience designing or standing up AI-native delivery organizations, innovation entities, or new operating model structures.
• Familiarity with modern enterprise delivery and planning tools such as Jira, Confluence, Smartsheet, Clarity, Power BI, or equivalent platforms.
• Bachelor’s degree in a relevant discipline required. Advanced degree, GCP certification, or program management certification advantageous.

Benefits at Gap Inc.

• Merchandise discount for our brands: 50% off regular-priced merchandise at Old Navy, Gap, Banana Republic and Athleta, and 30% off at Outlet for all employees.
• One of the most competitive Paid Time Off plans in the industry.
• Employees can take up to five "on the clock" hours each month to volunteer at a charity of their choice.
• Extensive 401(k) plan with company matching for contributions up to four percent of an employee’s base pay.
• Employee stock purchase plan.
• Medical, dental, vision and life insurance.
• See more of the benefits we offer.
• For eligible employees

Gap Inc. is an equal‑opportunity employer and is committed to providing a workplace free from harassment and discrimination. We are committed to recruiting, hiring, training and promoting qualified people of all backgrounds, and make all employment decisions without regard to any protected status. We have received numerous awards for our long-held commitment to equality and will continue to foster a diverse and inclusive environment of belonging. In 2022, we were recognized by Forbes as one of the World's Best Employers and one of the Best Employers for Diversity.