Senior Director, Organizational Change Management - Product to Market Transformation (San Francisco or New York City Based)

About the Role

Senior Director, Organizational Change Management leads the Organizational Change Management (OCM) and Learning & Development (L&D) for a multi-year, enterprise-wide, transformational initiative for Gap, Inc. This role is responsible for delivering the change, communications, and enterprise learning strategies that drive adoption, build capability, and measure value realization for the programs objectives. You’ll partner closely with business leaders, HR, PMO, IT, and Communications to ensure people, processes, and technology changes land successfully and sustainably.

What You'll Do

• Strategy and Leadership
  • Lead the integrated OCM and L&D strategy for IndigoX aligned to program milestones and business outcomes.
  • Build and lead a high-performing team of OCM practitioners, L&D designers, facilitators, and change communications specialists.
  • Establish governance, operating rhythms, and standards for change execution, learning delivery, and measurement.
  • Serve as a trusted advisor to executive sponsors and program leadership, coaching leaders on change sponsorship and behaviors.
• Change Management Execution
  • Own the comprehensive change strategy (stakeholder engagement, impact assessments, change readiness, communications, training, and reinforcement).
  • Direct change impact analyses; define personas, journey maps, and adoption paths across audience segments (field, corporate, technical, vendor).
  • Scale a change champion network; equip leaders and managers with toolkits and talking points.
  • Partner with PMO and Tech to embed OCM in delivery cadences (stage gates, sprint reviews, release planning).
  • Oversee change risks and issues; implement mitigation and reinforcement strategies to sustain behavior change.
• Learning & Development
  • Own the L&D strategy for IndigoX, from capability needs analysis to curriculum design and delivery across modalities
  • Build persona-based learning journeys; define certification or accreditation pathways where relevant.
  • Oversee learning technology enablement,measurement, and reporting.
  • Drive capability building, reskilling/upskilling, and manager enablement programs tied to IndigoX adoption.
• Communications and Engagement
  • Partner with Corp Comms on the IndigoX change communications strategy; craft clear, compelling messages and narratives tailored to diverse audiences.
  • Establish a drumbeat of communications (executive updates, roadshows, demos, office hours) that drive awareness and advocacy.
  • Partner with internal comms/brand teams to ensure alignment, tone, and reach across channels.
• Measurement and Value Realization
  • Define KPIs and dashboards for adoption, engagement, training effectiveness, time-to-proficiency, and business outcomes.
  • Set success criteria and leading indicators; run readiness reviews and post-implementation sustainment plans.
  • Conduct benefits realization reviews, lessons learned, and continuous improvement cycles across waves/releases.
• Operations
  • Standardize templates, playbooks, and toolkits; enable reusable assets across waves and workstreams.

Who You Are

• Required
  • 12+ years of experience in organizational change management and learning & development, including 5+ years leading large-scale transformations.
  • Demonstrated success designing and executing enterprise OCM and L&D strategies for complex, multi-year programs.
  • Strong leadership experience building and managing cross-functional teams and change networks.
  • Expertise in change methodologies (e.g., Prosci/ADKAR, Kotter, CCMP) and learning design principles.
  • Proven ability to partner with executive sponsors and communicate effectively with all levels, from frontline to C‑suite.
  • Data-driven approach; experience defining KPIs, building dashboards, and using insights to drive action.
  • Excellent storytelling, facilitation, and written communication skills.
• Preferred
  • Experience in large-scale technology-enabled transformations
  • Experience in retail change enablement
  • Background in HR, Talent, or OD strongly preferred.