Head of Technology Portfolio – Program Management

Job not on LinkedIn

🔥 1 minute ago

🇺🇸 United States – Remote

💵 $198k - $330k / year

⏰ Full Time

🔴 Lead

👨‍💼 Chief Technology Officer (CTO)

🦅 H1B Visa Sponsor

This company has sponsored H1B visas in the past.

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Stitch Fix

WebsiteLinkedInAll Job Openings

5001 - 10000 employees

Founded 2011

📣 Marketing

📦 Logistics

💼 Consulting

💰 $36.9M Venture Round on 2017-11

Marketing • Logistics • Consulting

Stitch Fix is a personal styling service that offers a unique and personalized approach to fashion for women, men, and kids. Clients start by taking a style quiz, which helps Stitch Fix understand their preferences, sizes, and budget. Based on this information, a personal stylist selects five personalized clothing pieces that are shipped directly to the client's door. Customers can choose to keep and purchase any items they like, with the $20 styling fee applicable to kept items. Stitch Fix carries a wide range of sizes and offers free shipping and returns. The service is flexible, with no subscription required, allowing customers to order style boxes on demand or at regular intervals. Stitch Fix also offers a 'Freestyle' shopping option where clients can browse curated suggestions based on their preferences. The company covers a wide variety of styles from numerous brands, ensuring there are options to suit various fashion tastes and needs.

📋 Description

• Lead the Technology Portfolio Management and Program Office function • Build capabilities, operating mechanisms, and talent for managing a multi-year product and technology portfolio • Translate business strategy into an integrated portfolio with priorities, investment choices, capacity commitments, milestones, dependencies, and success measures • Establish a trusted view of portfolio health, delivery timelines, capacity, risks, decisions, and outcomes • Design and run portfolio governance for sequencing, investment, scope, and trade-off decisions • Build and develop a high-performing team of technical program managers and portfolio-management practitioners • Create an integrated planning cadence across product roadmaps, architecture and platform dependencies, data and AI initiatives, enterprise systems, and operational readiness • Improve delivery predictability through capacity planning, dependency management, risk escalation, release readiness, and executive reporting • Define portfolio metrics covering outcomes, milestones, flow, cycle time, delivery predictability, capacity, quality, reliability, and strategic investment mix • Surface and resolve systemic execution blockers • Partner with Finance, Strategy & Transformation, Operations, Merchandising, Marketing, Legal, People, Security, and IT • Advance Jira and work-management discipline • Establish shared portfolio visibility, stronger alignment, clearer ownership, fewer blockers, and more predictable delivery

🎯 Requirements

• Significant leadership experience in technology portfolio management, a technical program management office, product operations, engineering operations, or a comparable enterprise delivery function • 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 • 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 • Analytical rigor and ability to design practical metrics, dashboards, and early-warning mechanisms • Exceptional executive communication skills • Collaborative, low-ego leadership style • Bias for action, high standards, and resilience to lead change in an environment with legacy complexity, evolving priorities, and ambitious transformation goals

🏖️ Benefits

• Competitive salary • Equity • Annual bonus • New hire and ongoing restricted stock unit grants, depending on employee and company performance • Medical benefits • Dental benefits • Vision benefits • Other benefits • Meaningful career growth • Collaborative, low-ego environment where diverse perspectives are celebrated