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About the Role

The Senior Director, Digital Workspace owns the global strategy, operations, and continuous evolution of technology experiences for all Gap Inc. employees, field teams, and business partners. This leader has enterprise-wide accountability across End User Computing, Deskside Support and Tech Bar, Executive Support, Merchandising Technical Support (GIS), and AI Tool Operations — ensuring every touchpoint is seamless, secure, and strategically aligned to the company's digital future. Operating at the intersection of people, platform, and performance, this role translates enterprise technology strategy into measurable outcomes at scale.

Responsibilities

Sets direction, removes friction, and builds organizations that consistently outperform.
Earns trust across executive, business, and technology partners by delivering results and communicating with clarity.
Operates with deep analytical skills, making data-driven decisions.
Leads AI-enabled transformation, distinguishing between impressive pilots and scalable programs.
Develops talent, builds inclusive cultures, and maintains high standards without burnout.
Operates with ambiguity at the intersection of corporate strategy and hands-on operational delivery.
Defines the multi-year technical roadmap for end user computing, workplace technology, and AI tool operations aligned to enterprise architecture standards.
Owns the global device and application ecosystem, including engineering standards, provisioning, security, and lifecycle policy.
Drives the evaluation, selection, and scaled deployment of AI productivity tools, partnering with Security, Legal, and IT Architecture to establish governance frameworks.
Oversees GIS/Merchandising technical infrastructure, ensuring system reliability, integration health, and responsiveness to business-critical workflows.
Establishes and enforces endpoint security baselines in partnership with Cybersecurity.
Owns the global service delivery model across all functions, including SLAs, staffing, vendor performance, and budget accountability.
Builds and operates a data-driven performance management system, defining KPIs, publishing scorecards, and driving continuous improvement.
Leads automation and AI-driven deflection programs to reduce incident volume and accelerate resolution.
Directs global vendor and managed service relationships, negotiating contracts and enforcing SLAs.
Ensures business continuity and disaster recovery readiness for all workspace technologies.
Leads, develops, and retains a globally distributed organization, setting a culture of accountability, inclusion, and growth.
Serves as a senior technology voice in enterprise planning discussions, translating business priorities into executable workspace strategies.
Partners with HR, Real Estate, and Facilities on workplace strategy.
Represents Digital Workspace at the executive level, communicating program status, risk, and investment decisions.
Champions diversity, equity, and inclusion as a structural practice.

Requirements

12 or more years in IT Operations, End User Services, or Digital Workplace leadership, with at least 5 years managing multi-function global organizations.
Demonstrated success scaling technology support operations across international geographies and diverse workforce types.
Proven track record leading enterprise AI tool evaluation, governance, and adoption programs at scale.
Experience leading or closely partnering on Merchandising, GIS, or other business-critical application support environments.
Deep expertise in ITIL/ITSM frameworks, endpoint management platforms (Intune, JAMF, SCCM), and modern service delivery tooling.
Executive presence — comfort presenting strategy, managing stakeholders, and influencing decisions at the VP and C-suite level.
Financial acumen: experience owning multi-million dollar operating and capital budgets, headcount planning, and vendor negotiations.
Successful enterprise-scale deployment of AI productivity tools with clear governance, measurable adoption, and demonstrated ROI.

Skills

End User Computing — Device lifecycle management, OS and application engineering, hardware standards, and global provisioning operations.
Microsoft Intune, SCCM, and Jamf for endpoint management.
Deskside Support & Tech Bar — In-person and walk-up support.
Executive Support — White-glove, proactive technology support.
Merchandising Technical Support (GIS) — Specialized technology support for geospatial, planning, and merchandising tools.
AI Tool Operations — Governance, enablement, and scaled adoption of AI productivity tools.
Enterprise Thinking
Outcome Ownership
Strategic Foresight
Executive Credibility
Talent Multiplication
Responsible Innovation

Experience Level

Senior Director
12 or more years in IT Operations, End User Services, or Digital Workplace leadership
at least 5 years managing multi-function global organizations

About the Company

Gap Inc.

Equal Opportunity

Champion diversity, equity, and inclusion as a structural practice — in hiring, development, and how work gets done.