Senior Director – Observability | SRE

About the Role

The Senior Director – Observability and SRE, is a strategic leader accountable for ensuring the reliability, availability, and performance of the enterprise technology ecosystem. This role oversees Observability, Site Reliability Engineering (SRE), Visibility and Live Sight Insights. This leader drives operational excellence through a proactive strategy that combines process discipline, automation, observability, and real-time insights. They will partner closely with engineering, infrastructure, cybersecurity, and product teams to build and sustain systems that power Gap Inc.’s digital and in-store experiences. As a thought leader, the Sr. Director will shape the long-term vision for operational reliability, defining modern capabilities, optimizing service performance, and establishing an innovation-driven reliability culture.

What You'll Do

Strategic Leadership & Vision 

• Define and execute the enterprise Observability and SRE strategy, ensuring alignment with business objectives and technology roadmaps. 

• Lead transformation of Unified Observability for end-to-end visibility of systems to actively and proactively reduce mean time to resolve through critical path anomaly detection.

• Partner with senior technology and business leaders to embed reliability and performance metrics into product development and operational planning. 

Operational Excellence & Reliability Engineering 

• Lead Site Reliability Engineering (SRE) practices across platforms and services driving automation, self-healing capabilities, and proactive monitoring to achieve measurable service resiliency improvements. 

• Establish standards for availability, latency, scalability, and operational efficiency through engineering-driven reliability principles. 

• Champion reliability by design ensuring observability, capacity planning, and chaos testing are core to delivery processes. 

Mission Control & Live Sight Insights 

• Oversee the Mission Control organization responsible for real time system monitoring, across ecommerce, fulfillment centers, and stores.

• Drive adoption of Live Sight Insights to create predictive and actionable intelligence on service health and performance trends. 

• Enable enterprise visibility of key metrics through intuitive dashboards and business-impact-based alerting models. 

• Lead a platform governance mindset focusing on reliability, scalability, and ease of use. 

People Leadership & Culture 

• Build, inspire, and develop a high-performing global Observability and SRE team that embodies accountability, collaboration, and innovation. 

• Foster a culture of data driven decision making, continuous learning, and operational excellence. 

• Serve as a mentor and coach to emerging leaders raising the organizational bar for reliability engineering and service leadership. 

Cross-Functional Partnership 

• Work closely with Software Engineering, Infrastructure, Cybersecurity, and Business Technology teams to ensure reliability objectives are integrated end-to-end. 

• Partner with Enterprise Architecture and Program Management to align technology investments with reliability outcomes. 

• Act as a trusted advisor to executive leadership on reliability strategy, risk posture, and enterprise service health and performance. 

Who You Are

• Proven strategic leader with success driving operational transformation at scale in global, complex environments for more than 10 years. 

• Deep expertise in ITIL frameworks, SRE principles, and architecture, and modern observability and SRE practices. 

• Strong technical understanding across infrastructure, cloud operations, automation, and service management ecosystems. 

• Exceptional ability to influence at all levels translating technical reliability concepts into business impact and strategic value. 

• Passionate about developing people and creating a culture of ownership, reliability, and continuous improvement. 

• Demonstrated track record of leading large, diverse teams and delivering measurable improvements in service reliability, performance, and user satisfaction. 

• A high performing leader operating with strategic agility, executive presence, and the ability to build organizational alignment through clarity, accountability, and purpose.