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Senior Strategy Manager - AI & Employee Enablement

February 20, 2026

About the Role The Office of AI at Gap Inc. is seeking a Sr. Manager, AI Strategy & Enterprise Enablement to shape and scale the enterprise AI capabilities and employee-facing tools that enable tens of thousands of employees across Old Navy, Gap, Banana Republic, and Athleta to work smarter, faster, and more creatively. In this role, you will define the strategy and roadmap for AI-enabled platforms, enterprise systems, and productivity experiences that support teams across merchandising, supply chain, marketing, store operations, finance, HR, and more. The work spans employee touch points from onboarding and learning to career growth and day-to-day productivity. You’ll partner closely with senior leaders across technology, data, product, HR, and business operations to identify high-impact opportunities, guide multi-team pilots, and drive enterprise-wide adoption of new AI capabilities. This role sits at the center of enterprise transformation, focused on building the AI foundation and experiences that unlock operational excellence, engagement, and innovation from within. This role is a hybrid Product Manager, Strategist and Technologist. What You'll Do Collaborate with the enterprise teams to deliver the strategy, prioritization, and roadmap for AI driven enterprise enablement, spanning employee-facing tools and enterprise platform capabilities across all Gap Inc. brands and functions. Lead efforts across enterprise platforms and productivity tools, including ChatGPT, Claude, CoPilot, intelligent search, Workday, and many more systems and tools. Evaluate and prioritize enabling technologies (e.g., GenAI services, workflow automation, enterprise search, data integration/orchestration platforms) for integration into employee workflows and core systems. Identify high-impact opportunities to enhance employee experience and productivity through automation, personalization, and intelligent insights. Partner with HR, Technology, Data, Product, and Business Operations to embed AI into key workflows and employee touchpoints; reducing friction and improving usability across distributed teams (corporate, distribution centers, and stores). Guide cross-functional pilot programs from opportunity framing to execution to enterprise scaling; ensuring clear objectives, KPIs, adoption plans, and measurable impact. Oversee a portfolio of test-and-learn initiatives, ensuring disciplined execution, risk management, and continuity from pilot to operationalization. Conduct build vs. buy analysis across use cases, evaluating first party and partner technology solutions; ensure alignment with data governance and security principles. Develop business cases, investment recommendations, ROI narratives, and executive-level communications that articulate platform value and enterprise impact; share success stories that demonstrate tangible outcomes. Champion responsible, human-centered, inclusive AI enablement that supports diverse employee needs and promotes intuitive adoption. Who You Are 8–12+ years of experience in technology strategy, enterprise platforms, digital/employee enablement, AI enablement, or related fields. Deep understanding of enterprise technology ecosystems and how platform capabilities drive organizational efficiency and scale. Strong understanding of HR tech ecosystems (e.g., Workday, ServiceNow, internal communications tools) and how AI can enhance them. Proven ability to lead cross-functional, multi-stakeholder initiatives bridging technology, data, business operations, and employee experience. Experience identifying, shaping, and delivering enterprise platforms or internal tools for large, diverse user groups. Skilled in strategic planning, Agile delivery, portfolio management, stakeholder alignment, and business case development. Exceptional communicator who can translate complex AI and technical concepts into clear business value for senior and executive audiences. Passionate about empowering employees through technology and enabling responsible AI-driven transformation and equitable, accessible experiences. Preferred Qualifications Familiarity with GenAI platforms, enterprise assistants, and intelligent search architectures (e.g., RAG systems, LLMs, decision-support tools, document automation). Experience designing or implementing AI use cases in HR, employee experience, or internal productivity contexts. Experience with platform services, enterprise SaaS integrations, or internal tooling ecosystems. Strong analytical, synthesis, and presentation abilities. Experience leading multi-disciplinary teams and enabling adoption across varied employee populations. At Gap Inc., we’re more than the clothes we make. We’re a collective of brands united by the belief that real people can (and should) drive real change. We’re a company that’s been synonymous with equality and inclusivity since our founding. The first of our industry to translate our commitment to sustainability into true accountability. Made stronger by our global team’s unique personalities, passions and pride, we set out every day to make the world a bit bolder and a bit brighter.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...