Transition Program Manager Jobs in Castro Valley, CA

Who We Are

We are seeking a Principal Program Manager to strengthen execution across a diverse portfolio of enterprise technology initiatives. This senior individual-contributor role will partner with delivery, technology, and business leaders to mentor Project Managers, assess program health, challenge delivery plans, manage cross-program dependencies, and improve execution across complex implementations. The ideal candidate has repeatedly led multiple concurrent enterprise programs spanning ERP, payroll, finance, data, integrations, cloud, and application modernization and can elevate delivery performance through influence rather than direct people management.

What You'll Do

The Principal Program Manager is a senior individual contributor responsible for strengthening delivery excellence across a portfolio of complex enterprise technology initiatives. This role partners closely with the Director of Delivery, Project Managers, Portfolio Management, Agile Delivery, technology leaders, and business stakeholders to improve execution, identify risks early, and increase confidence in delivery outcomes.

The Principal Program Manager leads through experience, influence, and delivery expertise. The role will mentor Project Managers, conduct independent delivery health assessments, support recovery of challenged initiatives, and establish consistent practices across programs spanning ERP, payroll, finance, data platforms, cloud technologies, and enterprise integrations.

Enterprise Delivery Leadership

• Provide senior delivery leadership across multiple concurrent enterprise technology programs.
• Evaluate overall program health, including scope, schedule, budget, resources, dependencies, risks, and business readiness.
• Challenge delivery assumptions and ensure plans reflect the full complexity of technical and business work.
• Identify emerging issues before they affect major milestones, budgets, or business outcomes.
• Support the recovery and stabilization of programs that are behind schedule, over budget, or otherwise at risk.
• Serve as a trusted escalation and problem-solving partner before issues require executive intervention.

Program Manager Coaching

• Mentor and coach Project and Program Managers responsible for complex technology implementations.
• Help PMs develop realistic integrated schedules, critical paths, resource plans, dependency maps, and recovery strategies.
• Strengthen PM capabilities in executive communication, financial management, risk management, testing governance, cutover planning, and stakeholder leadership.
• Promote accountability, transparency, business awareness, and disciplined execution across the delivery organization.
• Facilitate knowledge sharing and continuous improvement within the Project Management community.

Delivery Assurance

• Lead independent delivery health reviews for strategic programs.
• Assess readiness at key stage gates, including planning, define, build, testing, deployment, and transition to operations.
• Review complex areas such as data conversion, enterprise integrations, testing, security, archival, cutover, and production readiness.
• Ensure risks, assumptions, issues, dependencies, and decisions are clearly documented, owned, and actively managed.
• Validate that executive reporting accurately represents the health and outlook of each initiative.
• Provide clear recommendations regarding corrective actions, scope decisions, sequencing, and go-live readiness.

Cross-Program Coordination

• Partner with the Agile (SAFe) Manager to evaluate capacity, sequencing, and cross-program dependencies.
• Identify conflicts involving shared resources, environments, vendors, release windows, and technical platforms.
• Help integrate Agile delivery practices with the governance required for large, multi-year programs.
• Work with technology and business leaders to align delivery plans with strategic priorities and operational constraints.
• Support portfolio-level reporting and executive decision-making.

Delivery Standards and Continuous Improvement

• Establish and improve scalable delivery standards appropriate for Agile and hybrid programs.
• Define expectations for schedules, financial controls, risk management, testing, cutover, governance, and executive reporting.
• Identify recurring delivery challenges and implement practical improvements across the organization.
• Encourage the appropriate use of metrics, tools, and delivery data to improve predictability and accountability.

What You'll Need

• 12 or more years of progressive experience leading enterprise technology programs, with significant responsibility for complex, implementations across multiple technical competencies
• Demonstrated experience overseeing multiple concurrent programs rather than only a single implementation.
• Experience delivering initiatives across several of the following areas:
  • ERP, HRIS, payroll, finance, or workforce-management systems
  • Enterprise integrations and middleware
  • Data platforms, data conversion, migration, and archival
  • Cloud platforms and infrastructure
  • Large-scale application modernization
  • Cybersecurity, controls, or regulatory compliance
• Experience leading programs with multi-million-dollar budgets, large cross-functional teams, multiple vendors, and executive governance.
• Strong understanding of the full delivery lifecycle, including discovery, planning, requirements, design, build, testing, deployment, cutover, warranty and operational transition.
• Demonstrated ability to assess challenged programs and develop actionable recovery plans.
• Experience coaching senior Project and Program Managers without relying on direct reporting authority.

The typical annual salary range for this position is shown below and is negotiable depending upon experience and location. The position is eligible for a discretionary annual bonus.

We offer exceptional earning potential and a competitive benefits package, including group health insurance benefits (medical, vision, dental), FSA and HSA healthcare accounts, life and accident insurance, adoption and fertility assistance, paid parental leave of up to 6 weeks, and short/long term disability. Robert Half provides paid time off for vacation, personal needs, and sick time. The amount of Choice Time Off (CTO) our people receive varies based on their years of service and is pro-rated based on the hours worked per week. A new hire earns up to 17 days of CTO per calendar year. Our people also receive up to 11 paid holidays per calendar year. We also offer the opportunity to contribute to our company 401(k) savings and investment plan or deferred compensation plan (if eligible), with an employer match of 100% on the first 3% of your contributions for eligible employees. Learn more at https://roberthalfbenefits.com.

Robert Half Inc. is an Equal Opportunity Employer. M/F/Disability/Veteran

As part of Robert Half's Corporate Services facility employment process, any offer of employment is contingent upon successful completion of a background check.

Our recruiters use their expertise and may utilize AI to help with their evaluation of candidates.

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For positions located in San Francisco, CA: Robert Half will consider qualified applicants with criminal histories in a manner consistent with the requirements of the San Francisco Fair Chance Ordinance.

For positions located in Los Angeles County, CA: Robert Half will consider for employment qualified applicants with arrest or conviction records in accordance with the Los Angeles County Fair Chance Ordinance for Employers and the California Fair Chance Act.