Sr 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.

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.

• 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.

• 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.

• Proven success leading enterprise transformation programs in…