Head of Tech Portfolio & Delivery Strategy

OpenKrill; United States; Remote; USD 198,000 - 330,000; Full time

Benefits offered by this job

Competitive compensation

Equity

Medical, dental, vision benefits

Job summary

Stitch Fix, Inc. seeks a Head of Technology Portfolio Management & Program Office to establish the operating rhythm and delivery transparency that turn strategy into measurable business and client impact.

You will connect product, engineering, data, and enterprise systems to ensure predictable outcomes. The role blends strategic leadership with hands-on execution, shaping prioritization, funding, governance, and delivery while improving accountability, quality, and speed across the Product &

Qualifications

• Significant leadership experience in technology portfolio management or equivalent delivery function.
• Proven ability to lead multi-team portfolios in digital, e-commerce, or similar environments.
• Strong command of portfolio planning, investment governance, and capacity planning.
• Ability to translate business strategy into clear, decision-ready narratives.

Responsibilities

• Lead the Technology Portfolio Management and Program Office function and build capabilities for a multi-year portfolio.
• Translate business strategy into an integrated portfolio with clear priorities and milestones.
• Establish a single, trusted view of portfolio health, timelines, capacity, risks, and outcomes.
• Design and run portfolio governance for sequencing, investment, scope, and trade-offs.
• Build a high-performing team of program managers and portfolio practitioners.
• Create an integrated planning cadence aligning product roadmaps, architecture, data, and readiness.

Skills

Leadership

Portfolio management

Agile methods

Executive communication

Cross-functional leadership

Data-driven decisions

Tools

Jira

Job description

Stitch Fix, Inc. seeks a Head of Technology Portfolio Management & Program Office to establish the operating rhythm and delivery transparency that turn strategy into measurable business and client impact.

You will connect product, engineering, data, and enterprise systems to ensure predictable outcomes. The role blends strategic leadership with hands-on execution, shaping prioritization, funding, governance, and delivery while improving accountability, quality, and speed across the Product &