Senior Director – Observability | SRE

Posted An Hour Ago
Be an Early Applicant
3 Locations
In-Office
Senior level
eCommerce • Fashion
The Role
Leads enterprise observability and Site Reliability Engineering strategy, overseeing real-time monitoring, reliability practices, automation, self-healing, performance optimization, and operational excellence. Builds and develops a global team while partnering with engineering, infrastructure, cybersecurity, architecture, product, and business leaders. Establishes reliability standards, drives predictive service insights, advises executives on technology risk and service health, and delivers measurable improvements in availability, scalability, performance, and incident resolution.
Summary Generated by Built In
About the RoleThe 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. 

Skills Required

  • More than 10 years of experience leading operational transformation at scale in global, complex environments
  • Deep expertise in ITIL frameworks and Site Reliability Engineering principles
  • Expertise in architecture and modern observability and SRE practices
  • Strong technical understanding of infrastructure, cloud operations, automation, and service management ecosystems
  • Ability to influence stakeholders at all levels and translate technical reliability concepts into business impact
  • Experience leading large, diverse teams
  • Track record of delivering measurable improvements in service reliability, performance, and user satisfaction
  • Strategic agility, executive presence, and ability to build organizational alignment

Gap (gapinc.com). Compensation & Benefits Highlights

The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Gap (gapinc.com). and has not been reviewed or approved by Gap (gapinc.com)..

  • Healthcare Strength Comprehensive medical, dental, and vision coverage is offered, alongside programs that support physical, mental, and financial wellbeing. Feedback suggests eligible employees can also leverage tools like FSAs and additional wellbeing resources.
  • Leave & Time Off Breadth Paid time off, company-paid holidays, and multiple leave options (sick, disability, and family leave) create broad time-away coverage. Some roles start with substantial PTO accrual and can access flexible leave arrangements.
  • Wellbeing & Lifestyle Benefits A generous cross-brand merchandise discount is a standout perk, complemented by commuter benefits, on-the-clock volunteer hours, and matching donations. Feedback suggests these lifestyle benefits add meaningful value beyond base pay.

Gap (gapinc.com). Insights

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The Company
HQ: San Francisco, CA
11,000 Employees
Year Founded: 1969

What We Do

In 1969, Don and Doris Fisher opened the first Gap store on Ocean Avenue in San Francisco. They wanted to make it easier to find a great pair of jeans, and they did. Their denim and records store was a hit, and it grew to become one of the world’s most iconic brands. Today we’re represented in more than 1400 stores in over 40 countries, and online. We have headquarters in New York, London, Shanghai, Tokyo, and, of course, San Francisco. Our unique aesthetic is optimistic cool, elevated American style. Our clothes are crafted with care, with focused attention to thoughtful design. We believe in staying true to our heritage while creating what’s next. Don and Doris Fisher always wanted to “do more than sell clothes.” They wanted to support the people who ran their company, to be active in their communities, and to have a positive impact on the world. Their vision helped transform retail, and we’re still following their lead. We stand for freedom and possibility for all; we champion diverse ideas that transcend generations, geographies and genders.

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