Head of Technology Portfolio & Program Management

Required

• This is what you’ll need to succeed in this role from day 1.
• Deep, hands-on technical leadership experience as a Chief Architect, Distinguished Engineer, VP of Architecture, or comparable role in a complex digital, e-commerce, marketplace, or consumer technology environment.
• A record of leading large-scale architecture modernization across distributed systems, cloud platforms, data ecosystems, integrations, and customer-facing applications.
• Expertise in designing resilient, scalable, secure, and observable systems, including reliability engineering, performance, disaster recovery, and operational excellence.
• Strong judgment on how to manage the tension between immediate product delivery and long-term platform health, with a demonstrated ability to make trade-offs explicit and actionable.
• Experience establishing architecture principles, technical standards, reference patterns, and governance practices that strengthen autonomy and execution rather than centralizing all decisions.
• Fluency in modern cloud-native engineering, APIs and event-driven integration, data platforms, AI and machine-learning foundations, security, and developer productivity practices.
• Ability to assess technology investments through business value, risk, lifecycle cost, scalability, and organizational capability, not solely technical elegance.
• Exceptional influence and communication skills, with the ability to earn trust from engineers, product leaders, executives, and non-technical business partners.
• A coaching-oriented leadership style that raises the technical bar, develops senior talent, and fosters constructive debate, curiosity, and accountability.
• A bias for pragmatic action, continuous improvement, and simple, durable solutions in environments with legacy complexity and evolving business needs.
• You’ll love working at Stitch Fix because you will...