Director of Observability

Stitch Fix is transforming the way people find what they love. Our technology teams have created unique, innovative software for customers, merchandising, styling, warehouse systems, and inventory management. We leverage customer data and user research to personalize our service and make smart bets. The result is a powerful offering to our customers and a successful business serving millions of men, women, and kids. 

We're looking for an experienced Director of Observability to build and lead a global team that will implement and grow the platform systems that bolster our products.  The Observability team will empower our product and engineering teams to deliver value to the end customer in a faster and more reliable approach by focusing on availability, reliability and scalability.

This new leader will bring expertise in building out mission-critical systems at scale that can evolve quickly with our rapidly growing business. Additionally, we are looking for leaders with a proven record of building world-class engineering teams that focus on scalability, flexibility, and most importantly resilience.

What You Will Do

• Build, lead and mentor an Observability team; create an environment of teamwork, trust, and mutual success
• Scale the organization responsible for telemetry frameworks used throughout the Stitch Fix infrastructure, cloud services, and products to capture, transport, store and analyze the telemetry data
• Manage the end-to-end experience which enables our engineering team by leveraging frameworks, tools, APIs and visualizations to better understand the behavior of features services, and infrastructure they own and maintain
• Drive the roadmap for the Observability platforms in conjunction with cross-functional partners. Bring together multiple perspectives and be the key connector in this important and highly visible role.
• Help educate partners on how to appropriately monitor features and services they own, provide visualizations for monitoring distributed systems, give guidance for reducing operational overhead, and support the delivery of unmatched availability to our customers
• Participate in deep technical design discussions within your team, across partner teams, and ensure that we’re building the right systems
• Influence leaders and teams to effect change across the technology organization.
• Be an evangelist for the Observability team and overall culture, both internally and externally.

What You Bring

• 10+ years of experience in related technology roles, with at least five years building and architecting software systems.  Previous experience delivering Observability at scale is required.
• 5+ years of experience as a People Manager.  Global team experience is a plus.
• You are an experienced leader, able to guide teams and executives through complex data-driven decisions
• Solid understanding of new technology stacks and key personas such as SRE/DevOps/ITOps
• Knowledge of the Observability/APM/AIOps market and key capabilities/differentiation across the categories
• Understanding of modern software development lifecycle using scalable Agile, including experience with CI/CD frameworks and continuous deployment
• Knowledge of ML landscape, tools and application of ML to solve specific user problems
• Experience managing teams that designed and operated critical infrastructure, observability and importantly with a culture that views availability as a software engineering problem.
• Proven track record of improving reliability, availability and performance of complex distributed cloud based systems.
• Experience identifying metrics, and using instrumentation to monitor products and systems.
• Strong communication and presentation skills

Why You’ll Love Working at Stitch Fix

• We are a group of bright, kind and goal oriented people. You can be your authentic self here, and are empowered to encourage others to do the same! 
• We are a successful, fast-growing company at the forefront of tech and fashion, redefining retail for the next generation
• We are a technologically and data-driven business
• We are committed to our clients and connected through our vision of “Transforming the way people find what they love”
• We love solving problems, thinking creatively and trying new things
• We believe in autonomy & taking initiative
• We are challenged, developed and have meaningful impact
• We take what we do seriously. We don’t take ourselves seriously
• We have a smart, experienced leadership team that wants to do it right & is open to new ideas
• We offer transparent, equitable, and competitive compensation based on your level to help eliminate bias in salaries, as well as equity and comprehensive health benefits.

• You will be proud to say that you work for Stitch Fix and will know that the work you do brings joy to our clients every day