Senior Director, Digital Workspace

About the Role

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.