Senior Director, Digital Workspace

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.

What You'll Do

• A senior operator and strategist who sets direction, removes friction, and builds organizations that consistently outperform.
• An enterprise leader who earns trust across executive, business, and technology partners by delivering results and communicating with clarity.
• Deeply analytical — you run on data, surface the signal in the noise, and make decisions others are still debating.
• Experienced leading AI-enabled transformation and know the difference between pilots that impress and programs that scale.
• A talent developer who grows leaders, builds inclusive cultures, and holds the bar high without burning teams out.
• Comfortable operating with ambiguity at the intersection of corporate strategy and hands-on operational delivery.

Who You Are

• End User Computing — Device lifecycle management, OS and application engineering, hardware standards, and global provisioning operations. Strong expertise in Microsoft Intune, SCCM, and Jamf for endpoint management.
• Deskside Support & Tech Bar — In-person and walk-up support across corporate campuses, distribution centers, and field locations worldwide.
• Executive Support — White-glove, proactive technology support for C-suite and senior leadership; anticipates needs, resolves issues before they surface.
• Merchandising Technical Support (GIS) — Specialized technology support for geospatial, planning, and merchandising tools critical to product and inventory decisions.
• AI Tool Operations — Governance, enablement, and scaled adoption of AI productivity tools across the enterprise; defines usage frameworks, measures value, and drives responsible deployment.
• Define the multi-year technical roadmap for end user computing, workplace technology, and AI tool operations aligned to enterprise architecture standards.
• Own the global device and application ecosystem — from engineering standards and zero-touch provisioning to security posture and lifecycle policy.
• Drive the evaluation, selection, and scaled deployment of AI productivity tools; partner with Security, Legal, and IT Architecture to establish governance frameworks.
• Oversee GIS/Merchandising technical infrastructure, ensuring system reliability, integration health, and responsiveness to business-critical workflows.
• Establish and enforce endpoint security baselines in partnership with Cybersecurity — MDM, patching cadence, data loss prevention, and privileged access.
• Own the global service delivery model across all five functions — including SLAs, staffing models, vendor performance, and budget accountability.
• Build and operate a data-driven performance management system: define KPIs, publish scorecards, and drive continuous improvement through root cause analysis.
• Lead automation and AI-driven deflection programs to reduce incident volume, accelerate resolution, and shift investment to higher-value work.
• Direct global vendor and managed service relationships; negotiate contracts, enforce SLAs, and hold partners accountable to outcomes.
• Ensure business continuity and disaster recovery readiness for all workspace technologies across global geographies.
• Lead, develop, and retain a globally distributed organization of technology professionals, managers, and directors — setting a culture of accountability, inclusion, and growth.
• Serve as a senior technology voice in enterprise planning discussions, translating business priorities into executable workspace strategies.
• Partner with HR, Real Estate, and Facilities on workplace strategy including new site build-outs, hybrid work technology, and the evolving employee experience.
• Represent Digital Workspace at the executive level — communicating program status, risk, and investment decisions with precision and confidence.
• Champion diversity, equity, and inclusion as a structural practice — in hiring, development, and how work gets done.
• Measurable improvement in employee digital experience scores and technology-related productivity metrics across all workforce segments.
• Significant reduction in incident volume and mean time to resolution through automation, AI deflection, and proactive monitoring.
• Executive support operation recognized for reliability and proactive service — zero surprises for senior leadership.
• GIS/Merchandising systems maintaining high availability SLAs aligned to planning calendar and business-critical decision cycles.
• A high-performing, diverse organization with strong retention, clear succession plans, and leaders ready to grow.
• Enterprise Thinking — Makes decisions that optimize for Gap Inc., not just the Digital Workspace function. Identifies and closes cross-functional gaps others step over.
• Outcome Ownership — Sets ambitious targets, builds the operating model to hit them, and holds self and team accountable when they don't.
• Strategic Foresight — Anticipates where the workplace technology landscape is heading and positions the organization ahead of the curve rather than reacting to it.
• Executive Credibility — Communicates with authority and precision; earns trust from peers and executive sponsors through reliability, not just relationship.
• Talent Multiplication — Invests in people development as a core job requirement; measures success by how many leaders they produce, not just metrics they own.
• Responsible Innovation — Drives adoption of emerging tools (AI, automation) with appropriate risk management, governance, and change management — moving fast without breaking trust.

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 (corporate, field, distribution).
• 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.