Technology Portfolio & Program Delivery Lead

Stitch Fix Annex

United States

Remote

USD 198,000 - 330,000

Full time

14 days+

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Job summary

Stitch Fix is seeking a Head of Technology Portfolio Management & Program Office to establish operating rhythm, portfolio discipline, and delivery transparency across Product & Technology. This strategic yet hands-on leader will connect product, engineering, data, platform, and business partners to convert investment decisions into reliable outcomes.

The role emphasizes prioritization, governance, accountability, and scalable collaboration with CPTO and senior leaders to optimize speed, quality,

Qualifications

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, with judgment to adapt methods to the work.
Analytical rigor and ability to design practical metrics, dashboards, and early-warning mechanisms that improve decisions and delivery outcomes.
Exceptional executive communication skills to distill dependencies, risks, and resource constraints into clear choices.
Collaborative, low-ego leadership style that earns trust across disciplines and enables alignment.
Bias for action, high standards, and resilience to lead change in complex environments.

Responsibilities

Lead the Technology Portfolio Management and Program Office function, building capabilities, operating mechanisms, and talent for a multi-year portfolio.
Partner with CPTO and leadership to translate business strategy into an integrated portfolio with priorities, investment choices, capacity, milestones, and success metrics.
Establish a single, trusted view of portfolio health, delivery timelines, capacity, risks, decisions, and outcomes across Product & Technology.
Design and run portfolio governance for sequencing, investment, scope, and trade-offs balancing near-term needs with modernization, reliability, security, and client trust.
Build a high-performing team of technical program managers and portfolio-management practitioners.
Create an integrated planning cadence synchronizing product roadmaps, architecture, data/AI initiatives, enterprise systems, and readiness.
Improve delivery predictability with data-driven capacity planning, dependency management, risk escalation, release readiness, and executive reporting.
Define portfolio metrics such as outcomes, milestones, flow, cycle-time, capacity allocation, quality, reliability, and strategic investment mix.
Surface and resolve systemic blockers like unclear ownership, cross-team dependencies, resource constraints, and decision latency.
Partner with Finance, Strategy, Operations, Merchandising, Marketing, Legal, People, Security, and IT to align investments with priorities.