Principal, Enterprise AI Strategy

The Gap•Folsom, CA

16h

About The Position

The Principal will own Enterprise Strategy within Gap Inc.’s Office of AI, forming and communicating the company’s point of view on AI capabilities, adoption, and market direction. The role evaluates developments in a fast-moving field, distinguishes meaningful capability shifts from noise, explains the reasoning in writing, and presents recommendations to executives who make decisions based on that analysis. The Principal also owns subsequent decisions about enterprise AI standards and tooling, partner direction, licensing and consumption costs, and whether the company is acquiring useful capability or underused licenses. The role influences AI policy, standards, and governed context so teams can act without unnecessary delays. It also serves as an AI partner to enterprise functions including Finance, HR, Legal, and GTS: understanding how they work, identifying where AI can change their work, connecting tools to existing systems, and demonstrating capability through working solutions. The Principal collaborates with domain leads, platform and process teams, and partners in Security, Legal, and Sourcing, while advising senior executives and teaching the organization how to assess and apply AI.

Requirements

At least 8 years of experience in technology strategy, research, investing, consulting, platform ownership, or an equivalent discipline.
At least 3 years spent closely tracking AI.
A defensible point of view on AI’s direction, with willingness to revise it as evidence changes.
Exceptional written and presentation communication skills, including persuasive long-form memos and executive presentations.
Ability to reason rigorously under uncertainty, state assumptions plainly, and be candid about what remains unknown.
Hands-on experience personally creating working agents, skills, and shared context, and ability to build prototypes.
Technical fluency sufficient to evaluate AI capabilities and build prototypes that resolve questions.
Ability to hold substantive roadmap conversations with frontier labs and platform vendors and influence what is offered.
Commercial acumen, including modeling tooling costs at scale across seats, consumption, and token spend.
Ability to serve as a trusted advisor to senior executives and translate frontier developments into actionable decisions.
Ability to collaborate with enterprise functions and understand their work and opportunities for AI.
Ability to teach others what new AI capabilities mean and how to assess their application.
Collaborative approach to working with domain leads, platform and process teams, and Security, Legal, and Sourcing partners.
Comfort working in ambiguity and making decisions before all information is available.
Hands-on fluency with large language model tooling, including projects, skills, connectors, MCP, and agent patterns.

Responsibilities

Form, defend, and revise Gap Inc.’s point of view on AI capability, adoption, and market direction.
Evaluate models, platforms, and emerging capabilities, and translate them into enterprise consequences and executive decisions.
Write persuasive memos and create executive-ready presentations to communicate analysis and recommendations.
Own decisions about enterprise AI tooling, including standardization, licensing, entitlements, and migration.
Model and manage tooling costs at scale across seats, consumption, and token spend.
Engage with frontier labs and major platform vendors on roadmaps and influence the offerings made available to Gap Inc.
Build working agents, skills, shared context, and prototypes to test capabilities and settle strategic questions.
Partner with Finance, HR, Legal, and GTS to understand their work, identify AI opportunities, integrate tools with existing systems, and prove capabilities.
Influence AI policy, standards, and governed context to help teams act before demand arrives.
Advise senior executives by translating frontier developments into decisions relevant to them.
Teach and build organizational understanding of what AI capabilities mean and how they may apply to people’s work.
Collaborate with domain leads, platform and process teams, and partners in Security, Legal, and Sourcing.