Apply

Ready to go for it?

AI Apply speeds things up—apply directly if you prefer.

FREE ACCESS
5,000–10,000 jobs/day
Scoutfield Logo

See all jobs on Scoutfield

Search thousands of fresh jobs every day.

Discover
  • Fresh listings
  • Fast filters
  • No subscription required
Create a free account and start exploring right away.
Stitch Fix

Head of Technology Portfolio – Program Management

Stitch Fix

. Lead the Technology Portfolio Management and Program Office function .

Posted 10/12/2026full-timeRemote • United StatesLead💰 $198,000 - $330,000 per yearWebsite

Core Competencies

Role fit
Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in technology portfolio management, including capacity planning, investment governance, and delivery operating models. Proven ability to lead high-performing teams and translate business strategy into actionable portfolio narratives.

Highest-signal resume keywords
Technology Portfolio ManagementTechnical Program ManagementAgile Product DevelopmentCapacity PlanningExecutive Communication

ATS Keywords

Tailor your resume
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills
Portfolio PlanningInvestment GovernanceTechnical Dependency ManagementDelivery Operating ModelsMetrics DesignDashboard CreationRisk EscalationRelease ReadinessData and AI InitiativesMulti-Team Portfolio Leadership
Soft Skills
Collaborative LeadershipAnalytical RigorBias for ActionResilienceLow-Ego Leadership
Tools & Technologies
JiraWork Management Tools
Industry Keywords
E-CommerceDigital EnvironmentProduct OperationsEngineering OperationsEnterprise Delivery

About the role

Key responsibilities & impact
  • 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

What you’ll need
  • 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

Comp & perks
  • 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