Job DescriptionAbout the TeamThe Director Technology - PMO is responsible for leading enterprise-wide project and program management across WSI Technology by strengthening project planning and execution, scaling flexible PMO standards, improving executive visibility, and increasing delivery accountability across Technology initiatives.
About the Role The Director will lead the next phase of WSI's PMO transformation, including refining and scaling an AI-native delivery platform currently under development. Priorities include integrating Jira, financial systems, resource data, and other delivery information to provide timely visibility into project execution, dependencies, risks, capacity constraints, and financial performance.
This role partners closely with the CTO, Product leaders, Engineering leaders, and Technology Finance. The Director will lead approximately six to seven PMO leaders and Program Managers and will be accountable for developing talent, raising performance standards, and shaping the PMO organization for future-state success.
Responsibilities - Lead enterprise-wide project and program management across the Technology organization, with primary accountability for planning quality and execution discipline; ensure major initiatives have credible, integrated, and actionable delivery plans.
- Establish scalable PMO standards for scope, milestones, dependencies, resources, risks, project health, testing, release readiness, escalation, and decision-making across Agile, product, program, and hybrid delivery models while minimizing unnecessary administrative burden.
- Hold PMO leaders and Program Managers accountable for execution and transparent reporting; challenge delivery assumptions and reported project health, require corrective-action or recovery plans when initiatives are off track, and ensure material risks, dependencies, resource constraints, trade-offs, and decision needs are surfaced and escalated early.
- Establish and lead Technology governance routines, including leadership reviews, program-health reviews, escalation forums, and executive reporting, providing concise communication on delivery progress, project health, risks, financial implications, trade-offs, corrective actions, and required decisions.
- Lead the refinement, integration, adoption, and scaling of WSI Technology's AI-native delivery platform, integrating Jira, financial, resource, and operational data to establish a trusted operating view for project planning, execution health, and leadership reporting.
- Advance AI-enabled estimation, project-health signals, automated stakeholder communications, and retrospective insights while establishing data quality, ownership, controls, traceability, and appropriate human oversight.
- Partner with Technology leaders to align capacity, priorities, delivery commitments, and measurable success criteria; identify resource constraints and cross-program dependencies, and influence Technology-wide resource allocation decisions.
- Allocate and prioritize PMO and Program Management resources based on initiative complexity, delivery risk, and organizational need.
- Partner with Technology Finance to connect delivery plans with budgets, forecasts, actuals, and financial variances while maintaining clear ownership of financial management.
- Lead, coach, and develop PMO leaders and Program Managers; strengthen succession, performance management, organizational capability, and the future-state PMO structure.
- Lead change adoption for new PMO practices, tools, and operating routines while building a culture of ownership, transparency, problem-solving, continuous learning, and measurable results.
- Establish and monitor PMO performance measures, including delivery predictability, milestone performance, risk identification, corrective-action effectiveness, platform adoption, reporting efficiency, data completeness, and stakeholder confidence.
Criteria- Bachelor's degree or equivalent work experience.
- PMP, PgMP, recognized Agile certification, or equivalent demonstrated mastery of enterprise program and delivery-management practices.
- At least 12 years of experience in program, portfolio, and/or Technology delivery leadership.
- At least five years of people-management experience, including managing other people managers.
- Experience leading complex, enterprise-scale Technology programs in retail, e-commerce, digital, supply chain, and/or omnichannel environments.
- Demonstrated success scaling PMO standards, delivery frameworks, and operating practices.
- Strong expertise in project planning, execution, risk management, dependency management, status reporting, and recovery planning.
- Demonstrated technical fluency across the software-development lifecycle, including architecture and integration dependencies, testing, release planning, implementation readiness, and operational stabilization.
- Experience partnering with Product and Engineering leaders across Agile, product, program, and hybrid delivery environments.
- Strong executive communication and stakeholder-influence skills.
- Experience identifying resource constraints and influencing capacity decisions.
- Demonstrated success developing leaders and managing organizational performance.
- Experience applying AI, automation, or analytics to delivery management, reporting, risk identification, or decision support.
- Experience leading organizational transformation in a complex, matrixed enterprise.
- Experience integrating Jira, financial, resource, and project data into enterprise delivery, reporting, or decision-support platforms preferred.
- Experience scaling AI-enabled delivery capabilities and transforming manual PMO processes into automated, data-driven operating models, including appropriate data governance and controls preferred.
- This role requires being onsite in the San Francisco, CA office Monday through Thursday.
Our Culture & Values We believe that taking care of our people is vital to our success and we strive to offer equitable and transparent practices for all. We prioritize connection, growth, and wellbeing.
People First Putting People First means investing in overall well-being and opportunities to grow and advance within the organization. Depending on the position and location, here are a few highlights of what benefits may be available:
Benefits
- A generous discount on all WSI brands
- A 401(k) plan and other investment opportunities
- Paid vacations, holidays, and time off to volunteer
- Health benefits, dental and vision insurance, including same-sex domestic partner benefits
- Tax-free commuter benefits
- A wellness program that supports your physical, financial and emotional health
Continued Learning
- In-person and online learning opportunities through WSI University
- Cross-brand and cross-function career opportunities
- Resources for self-development
- Advisor (Mentor) program
- Career development workshops, learning programs, and speaker series
The expected starting pay range for this position is $205,000- $235,000. Applicable pay ranges may differ across markets. Actual pay will be determined based on experience and other job-related factors permitted by law. In addition to competitive pay, compensation may include a variety of other components like benefits, paid time off, merit, and bonus opportunities.
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