Senior Manager of Data Engineering and AI Automation, Business Systems

About the Team

The Business Systems team is the strategic technology and data partner for our company's core operations. We are the architects and owners of the tech stack that powers our Finance , Procurement, Merchandising and HR/ People and Culture functions.

We partner directly with business leaders to design, implement, and optimize scalable systems. But our work doesn't stop at the application layer. We are also responsible for transforming our business data into a strategic asset. Our team builds and manages the data engineering pipelines, analytics dashboards, and next-generation automation and Gen AI solutions that serve these functions. From core retail domain to our Stitch Fix specific data models, our work ensures data integrity, delivers critical insights, and empowers our leaders to make data-driven decisions. If you love solving complex business challenges with technology and data, and want to make a tangible impact on how our company operates, you'll fit right in.

About the Role

We're seeking a strategic Senior Engineering Manager to lead our Business Systems Data & Insights team, serving critical domains including Finance (Accounting, FP&A), Merchandising, Procurement, and HR/People & Culture. This is a high-impact, high-visibility role where you will shape the future of how Stitch Fix leverages data and AI to drive key business decisions and directly influence company strategy.

You will be responsible for driving our data and AI transformation by building scalable data infrastructure, advancing analytics capabilities, implementing intelligent automation, and accelerating Gen AI adoption across these essential business functions.

You're excited about this opportunity because you will...

• Lead and Mentor a World-Class Team: Hire, develop, and lead a high-performing team of data engineers and automation specialists. Foster a culture of technical excellence and continuous improvement, empowering your team to build robust solutions for data, automation, and AI.
• Own Critical Data Infrastructure: Build and own end-to-end data solutions, including ETL/ELT processing frameworks, data orchestration, metrics frameworks, and scalable data models optimized for retail financial data, P&C/HR analytics, and operational metrics.
• Drive AI & Automation Innovation: Establish and evolve automation and Gen AI frameworks purpose-built for Finance and HR. You will drive innovation in Gen AI applications, creating agents and automation that fundamentally transform how these teams work.
• Ensure Financial & Data Integrity: Build robust, compliant systems that meet the highest standards for financial data integrity. You will ensure all data systems comply with SOX (Sarbanes-Oxley) requirements, implementing necessary controls and audit trails, while partnering with Compliance, Internal Audit, and Finance teams to meet all regulatory requirements (including GDPR, CCPA, etc.).
• Partner to Solve Complex Challenges: Collaborate closely with a diverse set of stakeholders—from business leaders in Finance and People & Culture to engineering partners in Product, Data Platform, and HRIS—to solve complex data and business challenges at scale.
• Define Strategy and Execute with Autonomy: You will have the autonomy to shape the team's strategic roadmap and investment priorities based on business impact. You will be responsible for both strategic planning and hands-on delivery, including enhancing current tools and providing direct support to your business partners.

We get excited about you because you have...

• 8+ years of professional experience in data engineering, analytics engineering, or related technical roles, with demonstrated progressive responsibility
• 3-5+ years of engineering management experience, leading teams of 3-10+ engineers with proven track record of building high-performing teams
• Expert-level Python and SQL skills with production-grade code quality and design patterns
• Hands-on experience building and scaling data pipelines using modern orchestration tools (Airflow, or similar)
• Deep understanding of data modeling, dimensional modeling, and data warehouse design patterns
• Experience with batch and stream processing using Spark, Flink, or similar distributed computing frameworks
• Proficiency with cloud data platforms (AWS, GCP, or Azure) and modern data stack tools
• Strong experience with BI and analytics tools (Looker, Tableau or similar)
• ETL/ELT development experience with tools like Fivetran, dbt, or custom frameworks
• Working knowledge of retail financial data (FP&A metrics, merchandise planning, corporate accounting, or procurement analytics)
• Familiarity with HR data models (headcount analytics, compensation, performance management, or recruiting metrics)
• Experience integrating with ERPs (Oracle Fusion, NetSuite, Workday or others) and connected planning tools (Anaplan, Adaptive Planning, Essbase)
• Understanding of SOX (Sarbanes-Oxley) compliance and IT general controls (ITGCs)
• Experience implementing data controls, audit trails, and access management for financial and HR systems
• Exceptional cross-functional communication skills—able to translate complex technical concepts for business audiences
• Strong prioritization skills with business impact and ROI in mind
• Experience working autonomously and taking ownership of complex projects from conception to deliver

Why you'll love working at Stitch Fix...

• We are a group of bright, kind people who are motivated by challenge. We value integrity, innovation and trust. You’ll bring these characteristics to life in everything you do at Stitch Fix.
• We cultivate a community of diverse perspectives— all voices are heard and valued.
• We are an innovative company and leverage our strengths in fashion and tech to disrupt the future of retail.
• We win as a team, commit to our work, and celebrate grit together because we value strong relationships.
• We boldly create the future while keeping equity and sustainability at the center of all that we do.
• We are the owners of our work and are energized by solving problems through a growth mindset lens. We think broadly and creatively through every situation to create meaningful impact.
• We offer comprehensive compensation packages and inclusive health and wellness benefits.