Senior Strategy Manager - AI & Employee Enablement

Gap Inc.•Pleasanton, CA

About The Position

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.

Requirements

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.

Nice To Haves

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.

Responsibilities

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.