Principal, Enterprise AI Strategy

About the Role

We are seeking a Principal to own Enterprise Strategy within the Office of AI. This is a strategy role in the truest sense: our view of where AI is going, and what Gap Inc. should do about it, will only be as good as the person forming it. The frontier moves every few weeks, most of what is published is noise, and the difference between a genuine capability shift and a release note is a judgment call few people make well. You will make that call, write down the reasoning, and take it to the executives who act on it.

You’ll then own the decisions that follow. What we standardize on and what we retire, where our partners are heading and what we should be asking them for, what our tooling costs as consumption scales, and whether we are buying capability or licenses nobody uses. You’ll influence the policy, standards and governed context the organization needs before the demand arrives rather than after it, so that teams have an answer instead of a queue.

You’ll also serve as the AI partner to our enterprise functions, including Finance, HR, Legal and GTS, because a strategy nobody can operationalize is not a strategy. That means understanding how those teams actually work, identifying where AI changes it, connecting the tooling to the systems they already run on, and proving the capability rather than describing it. This role suits someone rigorous, who can make an argument land in writing and in the room, who is technical enough to build the thing that settles it, and who is comfortable being the person whose analysis the company bets on.

What You’ll Do

Who You Are

• A strategist with 8+ years in technology strategy, research, investing, consulting, platform ownership or an equivalent discipline, with at least 3 years spent closely tracking AI

• Someone who holds a genuine thesis on where the technology is going, can defend it under pressure, and will change it when the evidence moves

• An exceptional communicator in both writing and presentation. Much of your influence will come through memos and through the decks you put in front of executives, and how well you make the case will decide whether anything happens

• A rigorous thinker who reasons under uncertainty, states assumptions plainly, and is honest about what is still unknown

• A hands-on builder who has personally created working agents, skills and shared context, and who will build a prototype to settle a question rather than keep debating it

• A credible partner to frontier labs and platform vendors, able to hold a substantive conversation about roadmap and influence what we are offered

• Commercially sharp, able to model what tooling costs at scale across seats, consumption and token spend, and to manage that cost deliberately rather than discover it

• A trusted advisor to senior executives, able to translate a frontier development into the decision it implies for them this quarter

• A collaborative partner to enterprise functions such as Finance, HR, Legal and GTS, able to understand how their work runs and where the opportunity actually sits

• A thought leader who teaches. You explain what new capability actually means, show people how to think about where it applies to their work, and make the organization smarter about AI rather than more reliant on you

• A natural collaborator who works shoulder to shoulder with our domain leads, our platform and process teams, and our partners in Security, Legal and Sourcing

• Someone who thrives in ambiguity and is comfortable making a call before the picture is complete

Who You Are

Competencies

• Forming, defending and revising a point of view on AI capability, adoption and market direction

• Exceptional written and visual communication, including persuasive long-form memos and executive-ready presentations

• Evaluation of models, platforms and emerging capability, and translation into enterprise consequence

• Enterprise tooling strategy, covering standardization, licensing, entitlement and migration

• Cost and consumption modelling, including token economics and platform trade-offs

• Partnership and commercial engagement with frontier labs and major platform vendors

• Hands-on fluency with large language model tooling, including projects, skills, connectors, MCP and agent patterns

• Thought leadership and collaboration across the organization, teaching what the technology can do and how to think about applying it

Location Area

2F (San Fr…