Remote opportunity at
Stitch FixHead of Technology Portfolio & Program Management
Stitch Fix operates in the retail sector, blending human creativity with data science and Generative AI to deliver personalized shopping experiences. The company is currently hiring…
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About This Role
Stitch Fix operates in the retail sector, blending human creativity with data science and Generative AI to deliver personalized shopping experiences. The company is currently hiring a Head of Technology Portfolio & Program Management to report directly to the Chief Product & Technology Officer. This remote, full-time position comes with an annual salary range of USD 198,000 to USD 330,000, along with equity, an annual bonus, and comprehensive benefits. In…
Job Description
Stitch Fix operates in the retail sector, blending human creativity with data science and Generative AI to deliver personalized shopping experiences. The company is currently hiring a Head of Technology Portfolio & Program Management to report directly to the Chief Product & Technology Officer. This remote, full-time position comes with an annual salary range of USD 198,000 to USD 330,000, along with equity, an annual bonus, and comprehensive benefits.
In this strategic yet hands-on capacity, the individual will shape how the Product & Technology organization prioritizes, funds, governs, and delivers major initiatives. The role involves setting up the operating rhythm, portfolio discipline, and delivery transparency needed to turn overarching business strategies into reliable outcomes. The successful candidate will connect product, engineering, data, platform, enterprise systems, and business units around a structured path from investment choices to client value.
Ideal candidates will bring substantial leadership experience managing complex, multi-team portfolios within digital, e-commerce, marketplace, or product-led environments. The position suits a collaborative leader with deep familiarity in agile methodologies, technical dependency management, and capacity planning. Strong executive communication skills and a low-ego approach are essential for aligning cross-functional partners across finance, strategy, marketing, operations, legal, and security. Responsibilities include building a high-performing technical program management team, establishing integrated planning cadences, designing portfolio governance, and tracking metrics related to predictability, flow, cycle-time, and investment mix.
Responsibilities
- Lead the Technology Portfolio Management and Program Office function to oversee a multi-year product and technology portfolio
- Partner with executive and technology leadership to transform business strategy into an integrated portfolio with clear priorities and capacity commitments
- Maintain a transparent, single source of truth regarding portfolio health, timelines, risks, and decisions across the Product & Technology organization
- Design and administer governance mechanisms for sequencing, investments, and trade-offs between business growth and platform modernization
- Build, develop, and mentor a high-performing team of technical program managers and portfolio practitioners
- Synchronize product roadmaps, data initiatives, platform dependencies, and operational readiness into an integrated planning cadence
- Drive delivery predictability using data-driven practices for capacity planning, dependency tracking, and risk escalation
- Define and monitor key portfolio metrics covering milestone progress, cycle-time health, quality, reliability, and strategic investment mix
- Identify and eliminate cross-team execution blockers, resource constraints, and architectural bottlenecks
- Collaborate closely with finance, strategy, merchandising, marketing, legal, people, security, and IT teams
Requirements
- Significant leadership background in technology portfolio management, technical program management, product operations, or engineering operations
- Proven track record of directing complex, multi-team portfolios in digital, e-commerce, marketplace, or product-led settings
- Strong command of portfolio planning, investment governance, scenario planning, and delivery operating models
- Demonstrated ability to connect business goals, customer impact, product roadmaps, and financial trade-offs
- Experience building and nurturing teams of technical program managers and delivery practitioners
- Deep fluency in agile and modern product-development practices
- Strong analytical capabilities to design metrics, dashboards, and early-warning systems
- Exceptional executive communication skills to distill complex dependencies into actionable choices
- Collaborative, low-ego leadership style focused on earning cross-disciplinary trust and managing difficult conversations
Core Skills
Benefits
- Competitive salary between USD 198,000 and 330,000 per year
- Annual bonus eligibility
- New hire and ongoing grants of restricted stock units
- Medical coverage
- Dental coverage
- Vision coverage
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
What is the location and remote policy for this role?
The position is designated as remote.
What is the salary range for the Head of Technology Portfolio & Program Management?
The annual salary ranges from USD 198,000 to 330,000, determined by factors such as professional background, experience, location, and performance.
What additional compensation is offered beyond base salary?
The role is eligible for an annual bonus as well as new hire and ongoing grants of restricted stock units, depending on individual and company performance.
How do candidates apply for this position?
Applicants should submit their applications through Stitch Fix's official career pages or designated application links provided in the posting.
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