Stitch Fix
Stitch Fix
Stitch Fix combines personal styling and online fashion shopping for women, men, and children. Clients share their preferences, sizes, and budget through a style quiz, then receive a handpicked selection of clothing from a personal stylist. They can buy the pieces they want or browse Freestyle, a shopping experience with recommendations tailored to their style. The service brings together fashion, data-informed recommendations, and logistics to deliver clothing directly to customers.

Head of Technology Portfolio and Program Management

Lead technology portfolio planning and program management at Stitch Fix, connecting product, engineering, and business investments to measurable outcomes. The role supports the company’s personalized retail model through data science and AI.

Description

  • Lead Stitch Fix’s Technology Portfolio Management and Program Office.
  • Develop the capabilities, operating practices, and talent needed to manage a multiyear product and technology portfolio.
  • Turn business strategy into an integrated portfolio with priorities, investment decisions, capacity commitments, milestones, dependencies, and success measures.
  • Maintain a reliable view of portfolio health, delivery timelines, capacity, risks, decisions, and outcomes.
  • Design and oversee governance for sequencing, investment, scope, and trade-off decisions.
  • Build and develop a strong team of technical program managers and portfolio management practitioners.
  • Coordinate planning 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.
  • Set portfolio metrics for outcomes, milestones, flow, cycle time, delivery predictability, capacity, quality, reliability, and strategic investment mix.
  • Identify and address systemic execution blockers.
  • Work with Finance, Strategy & Transformation, Operations, Merchandising, Marketing, Legal, People, Security, and IT.
  • Strengthen Jira practices and work management.
  • Create shared portfolio visibility, better alignment, clear ownership, fewer blockers, and more predictable delivery.

Requirements

  • Substantial leadership experience in technology portfolio management, a technical program management office, product operations, engineering operations, or a similar enterprise delivery function.
  • Track record leading complex portfolios across multiple teams in a product-led, digital, e-commerce, marketplace, or comparably fast-moving environment.
  • Strong command of portfolio planning, investment governance, capacity and scenario planning, technical dependencies, and delivery operating models.
  • Ability to connect business strategy, customer impact, product roadmaps, technology architecture, and financial trade-offs in 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 knowledge of agile methods and modern product development practices.
  • Strong analytical skills and ability to create practical metrics, dashboards, and early-warning mechanisms.
  • Excellent executive communication skills.
  • Collaborative leadership style with low ego.
  • Bias for action, high standards, and resilience to lead change amid legacy complexity, shifting priorities, and ambitious transformation goals.

Benefits

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

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