Head of Technology Portfolio & Program Management

About the Role

Reporting to the Chief Product & Technology Officer, the Head of Technology Portfolio Management & Program Office will establish the operating rhythm, portfolio discipline, and delivery transparency that enable Stitch Fix to turn strategy into meaningful business and client impact. This leader will connect product, engineering, data, platform, enterprise systems, and business partners around a clear, durable path from investment decisions to reliable outcomes.

The role is both strategic and hands-on: shaping how the Product & Technology organization prioritizes, plans, funds, governs, and delivers its most important work while strengthening accountability, predictability, quality, and speed. The ideal leader brings sound judgment, empathy, and the ability to make complex trade-offs visible and actionable.

Responsibilities:

• Lead the Technology Portfolio Management and Program Office function, building the capabilities, operating mechanisms, and talent needed to manage a multi-year product and technology portfolio.
• Partner with the CPTO and Product & Technology leadership to translate business strategy into an integrated portfolio, with clear priorities, investment choices, capacity commitments, milestones, dependencies, and success measures.
• Establish a single, trusted view of portfolio health, delivery timelines, capacity, risks, decisions, and outcomes across the Product & Technology organization.
• Design and run portfolio governance that enables timely decisions on sequencing, investment, scope, and trade-offs, balancing near-term business needs with platform modernization, reliability, security, and client trust.
• Build a high-performing team of technical program managers and portfolio-management practitioners; set clear expectations, develop talent, and embed the team as strategic partners with product and engineering leaders.
• Create an integrated planning cadence that synchronizes product roadmaps, architecture and platform dependencies, data and AI initiatives, enterprise systems, and operational readiness.
• Improve delivery predictability by introducing lightweight, data-driven practices for capacity planning, dependency management, risk escalation, release readiness, and executive reporting.
• Define the portfolio metrics that matter, including outcome and milestone progress, flow and cycle-time health, delivery predictability, capacity allocation, quality, reliability, and strategic investment mix.
• Surface and resolve systemic execution blockers, including unclear ownership, cross-team dependencies, resource constraints, architecture bottlenecks, and decision latency.
• Partner closely with Finance, Strategy & Transformation, Operations, Merchandising, Marketing, Legal, People, Security, and IT to align technology investments with enterprise priorities and operating realities.
• Advance a pragmatic, modern operating model that strengthens Jira and work-management discipline without adding unnecessary process burden to teams.
• Model a culture of accountability, learning, inclusivity, and continuous improvement, ensuring teams can move quickly while protecting quality, stability, security, and the client experience.

Responsibilities:

•  A clear, shared portfolio that connects Product & Technology investments to Stitch Fix business priorities, client value, and measurable outcomes.
• Leaders have timely, trusted visibility into commitments, capacity, dependencies, risks, and decisions, enabling faster and higher-quality trade-offs.
• Teams experience stronger cross-functional alignment, clearer ownership, fewer avoidable blockers, and more predictable delivery of valuable product and platform capabilities.
• The organization can balance growth initiatives with modernization, reliability, security, and operational commitments through transparent investment choices.
• Portfolio and delivery practices are scalable, useful, and adopted because they make teams more effective rather than simply more reportable.

About You

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

Requirements:

• Significant leadership experience in technology portfolio management, a technical program management office, product operations, engineering operations, or a comparable enterprise delivery function.
• A proven record of leading complex, multi-team portfolios in a product-led, digital, e-commerce, marketplace, or similarly dynamic environment.
• Strong command of portfolio planning, investment governance, capacity and scenario planning, technical dependency management, and delivery operating models.
• The ability to connect business strategy, customer impact, product roadmaps, technology architecture, and financial trade-offs into clear, decision-ready narratives.
• Experience building and developing teams of technical program managers, program leaders, scrum or delivery practitioners, and cross-functional operating partners.
• Deep fluency with agile and modern product-development practices, paired with the judgment to adapt methods to the work rather than applying processes rigidly.
• Analytical rigor and the ability to design practical metrics, dashboards, and early-warning mechanisms that improve decisions and delivery outcomes.
• Exceptional executive communication skills, including the ability to distill complex dependencies, risks, and resource constraints into clear choices and actions.
• A collaborative, low-ego leadership style that earns trust across disciplines, facilitates difficult conversations, and creates alignment without over-centralizing decisions.
• A bias for action, high standards, and the resilience to lead change in an environment with legacy complexity, evolving priorities, and ambitious transformation goals.

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.