Lead Engineer, Order Management

About the Role

As a Lead Engineer on the Order Management team, you will help set the technical direction for the systems that power checkout, order creation and lifecycle management, fulfillment orchestration, and integrations with critical internal and third-party partners. This is a hands-on technical leadership role where you will own complex initiatives from discovery through delivery, translating business and operational objectives into scalable technical solutions.

You will partner closely with Product Managers, Engineering Managers, engineers, and teams across Inventory, Fulfillment, Client Experience, and Operations to coordinate work across services, data flows, and operational processes. You will design and build production systems, lead technical decisions through ambiguity, and raise the bar for reliability, maintainability, and operational readiness. Your work will directly impact client trust, revenue, and the efficiency of our fulfillment operations.

Responsibilities:

• Lead complex, multi-sprint Order Management initiatives from problem framing and technical design through implementation, production rollout, and post-launch measurement, independently owning outcomes and driving execution through ambiguity.
• Design and build reliable, stateful services and workflows across checkout, order lifecycle management, fulfillment orchestration, and partner integrations, with a focus on correctness, data consistency, scalability, and explicit failure and recovery patterns.
• Drive technical decisions by evaluating and documenting options, constraints, and tradeoffs, while balancing near-term delivery with long-term maintainability, system simplification, technical debt reduction, and engineering velocity.
• Partner with Product, Engineering, and cross-functional teams to define scope, milestones, estimates, dependencies, success criteria, and delivery risks, connecting technical decisions to measurable client, business, and operational outcomes.
• Strengthen engineering and operational excellence through automated testing, observability, safe rollout and rollback strategies, incident leadership, post-incident remediation, code and design reviews, and mentorship that raises engineering standards across the team.

How AI and tools show up in your day-to-day work:

• Use AI-assisted development tools to accelerate discovery, implementation, testing, debugging, documentation, and problem-solving while applying strong engineering judgment to validate outputs and ensure production quality.
• Work across our engineering ecosystem, including Golang, Ruby on Rails, PostgreSQL, AWS, Kafka, Temporal, and Datadog, to build, operate, and continuously improve business-critical systems.
• Evaluate and adopt new AI capabilities, engineering tools, and technologies that improve developer productivity, system reliability, and the speed and quality of delivery.

About You

This is what you’ll need to succeed in this role from day 1.

Requirements:

• You have 5+ years of software engineering experience, with demonstrated impact building and operating complex, business-critical backend, distributed, or workflow systems with high correctness and availability requirements.
• You are fluent in at least one modern programming language, such as Go, Ruby, Java, or Python, and are comfortable learning and working across languages. Our current stack is primarily Golang and Ruby.
• You have strong experience with relational databases such as PostgreSQL or MySQL, including data modeling, transactional semantics, schema evolution, and performance considerations, as well as experience operating services on a major cloud platform such as AWS, GCP, or Azure.
• You have a track record of independently leading complex, multi-sprint initiatives from discovery and design through launch and operational follow-through, translating ambiguity into clear technical direction and measurable outcomes.
• You communicate clearly in writing and conversation, translate technical complexity into business outcomes, and collaborate effectively across Product, Engineering, Operations, and other technical and non-technical partners.
• You bring a well-reasoned technical point of view while remaining open to evidence, alternative perspectives, and better solutions, and you use your expertise to mentor engineers and raise the technical bar for the broader team.
• You value automated testing, continuous delivery, observability, safe releases, reliability, and incident learning as essential components of engineering quality.
• You are fluent with AI-assisted software development tools, such as ChatGPT, GitHub Copilot, or similar technologies, and use them thoughtfully to improve engineering efficiency and outcomes.
• You have a bachelor’s degree in Engineering, Computer Science, or a related field, or equivalent practical experience.

Nice to Have:

• Experience working in e-commerce, order management, payments, inventory, logistics, fulfillment, or another high-throughput transactional domain.
• Experience designing integrations with third-party systems and accounting for partial failure, latency, consistency, recovery, and partner operational constraints.
• Familiarity with technologies in our ecosystem, including Golang, Ruby on Rails, PostgreSQL, AWS, Kafka, Temporal, and Datadog; experience with these specific technologies is helpful but not required.

You’ll love working at Stitch Fix because you will…

• Fuse human creativity and styling expertise to redefine personalized retail.
• Set a high bar for our craft and drive measurable impact across fashion, tech, and data science.
• Actively leverage AI and modern tech to evolve how work gets done.
• Lead with innovation, think boldly, and aren't afraid to challenge conventional retail norms.
• Win together in a collaborative, low-ego environment where diverse perspectives are celebrated.
• Be client obsessed by putting our customers at the heart of every decision to deliver unmatched personalization and trust.
• Support our team with competitive compensation packages, comprehensive benefits, and meaningful career growth.