Head of Technology Portfolio – Program Management

This is a fully remote position, open to applicants in United States.

📋 Description

• Oversee the Technology Portfolio Management and Program Office function.

• Develop capabilities, operational mechanisms, and talent to manage a multi-year product and technology portfolio.

• Convert business strategy into a cohesive portfolio that includes priorities, investment selections, capacity commitments, milestones, dependencies, and success metrics.

• Create a reliable view of portfolio health, delivery timelines, available capacity, risks, decisions, and outcomes.

• Design and implement portfolio governance for sequencing, investment, scope, and trade-off decisions.

• Build and nurture a high-performing team of technical program managers and portfolio-management professionals.

• Establish an integrated planning rhythm across product roadmaps, architecture and platform dependencies, data and AI initiatives, enterprise systems, and operational readiness.

• Enhance delivery predictability through effective capacity planning, dependency management, risk escalation, release readiness, and executive reporting.

• Define portfolio metrics encompassing outcomes, milestones, flow, cycle time, delivery predictability, capacity, quality, reliability, and strategic investment mix.

• Identify and address systemic execution barriers.

• Collaborate with Finance, Strategy & Transformation, Operations, Merchandising, Marketing, Legal, People, Security, and IT.

• Promote Jira and work-management discipline.

• Create shared portfolio visibility, enhance alignment, clarify ownership, reduce blockers, and improve delivery predictability.

⛳️ Requirements

• Extensive leadership experience in technology portfolio management, a technical program management office, product operations, engineering operations, or a similar enterprise delivery function.

• Demonstrated success in leading complex, multi-team portfolios in a product-driven, digital, e-commerce, marketplace, or similarly fast-paced environment.

• Strong expertise in portfolio planning, investment governance, capacity and scenario planning, technical dependency management, and delivery operating models.

• Ability to link business strategy, customer impact, product roadmaps, technology architecture, and financial trade-offs into concise, decision-ready narratives.

• Experience in building and developing teams of technical program managers, program leaders, scrum or delivery practitioners, and cross-functional operating partners.

• Deep knowledge of agile and contemporary product-development practices.

• Analytical rigor with the ability to design practical metrics, dashboards, and early-warning systems.

• Outstanding executive communication skills.

• Collaborative, humble leadership style.

• Proactive mindset, high standards, and resilience to drive change in an environment characterized by legacy complexities, shifting priorities, and ambitious transformation goals.

🏝️ Benefits

• Competitive salary.

• Equity opportunities.

• Annual bonus structure.

• New hire and ongoing restricted stock unit grants based on employee and company performance.

• Comprehensive medical benefits.

• Dental coverage.

• Vision care benefits.

• Additional benefits.

• Meaningful opportunities for career advancement.

• A collaborative, low-ego environment that values diverse perspectives.