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[Remote] Senior Manager of Data Engineering and AI Automation, Business Systems

March 6, 2026

Note: The job is a remote job and is open to candidates in USA. Stitch Fix is the leading online personal styling service, helping clients discover styles that fit their individual tastes. They are seeking a Senior Engineering Manager to lead the Business Systems Data & Insights team, focusing on building scalable data infrastructure and driving AI transformation to influence key business decisions.

Responsibilities

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

Skills

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

Benefits

Medical
Dental
Vision
Annual bonus
Restricted stock units

Company Overview

Stitch Fix is a personal styling platform that delivers curated and personalized apparel and accessory items for women. It was founded in 2011, and is headquartered in San Francisco, California, USA, with a workforce of 1001-5000 employees. Its website is http://stitchfix.com.

Company H1B Sponsorship

Stitch Fix has a track record of offering H1B sponsorships, with 22 in 2025, 18 in 2024, 17 in 2023, 45 in 2022, 34 in 2021, 30 in 2020. Please note that this does not guarantee sponsorship for this specific role.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...