Corporate Vice President - Head of Transformation Management Office

As the Head of the Transformation Management Office (TMO) within Technology’s COO organization, you will lead the orchestration of New York Life’s multi-year transformation agenda across Technology, Data, and AI (TDAV). This role oversees how transformation initiatives are governed, prioritized, and executed—ensuring alignment to strategic outcomes in modernization, workforce evolution, and value realization. 

You will define the TMO’s operating model, establish delivery standards, and personally manage several high-impact initiatives while coaching and developing a team of program and project managers. Acting as both a strategist and execution leader, you will set the bar for delivery excellence, cross-functional partnership, and outcome-based transformation. 

This role requires a strategic operator and transformation catalyst—someone who brings deep program delivery experience, fluency in Agile and change methodologies, and the leadership presence to influence at all levels of the organization. 

What You’ll Do 

1. Build and Lead a High-Performing TMO Team 

• Lead, coach, and develop a team of transformation program and project managers responsible for delivering cross-Technology initiatives. 

• Build a unified identity for the TMO as a center of excellence for delivery discipline, change enablement, and transformation leadership. 

• Establish performance standards, clear accountability, and skill development pathways aligned to the future-state TDAV operating model. 

• Act as a working lead — directly manage a portfolio of strategic programs to model best-in-class delivery, stakeholder engagement, and reporting practices. 

2. Establish and Operationalize the TMO 

• Define and implement a modern TMO framework that integrates transformation planning, delivery governance, and change enablement across TDAV. 

• Develop consistent processes for intake, prioritization, and performance measurement that link execution to enterprise strategic outcomes. 

• Standardize portfolio tools, reporting, and success metrics to provide transparent visibility into progress, risks, and value realization. 

• Partner with TDAV, Finance, HR, and business leaders to align priorities, optimize resourcing, and enable efficient delivery of the transformation roadmap. 

3. Drive Delivery Excellence and Transformation Outcomes 

• Oversee execution of complex, cross-domain transformation programs—ensuring clear ownership, alignment, and outcome-based delivery. 

• Personally lead key enterprise initiatives or recovery efforts that require elevated visibility, hands-on coordination, and executive engagement. 

• Equip program managers to lead initiatives that span people, process, and technology, integrating Agile and Product delivery models where applicable. 

• Champion continuous improvement through retrospectives, playbooks, and portfolio insights that evolve how we plan, deliver, and measure success. 

• Serve as a trusted advisor to senior leaders, translating progress and value realization into clear, data-driven executive narratives. 

4. Foster a Culture of Continuous Improvement and Accountability 

• Embed a mindset of adaptability, learning, and transparency within the TMO and across the broader TDAV organization. 

• Promote an environment that balances structure with flexibility—enabling teams to deliver with speed, accountability, and measurable impact. 

What You’ll Bring 

Strategic and Delivery Leadership 

• Proven ability to design and lead enterprise-level PMOs or large program management functions. 

• Demonstrated success managing cross-functional portfolios that combine technology, data, and business transformation. 

• Experience acting as both strategist and hands-on program leader — comfortable shifting between setting direction and diving into execution. 

Execution Excellence 

• Expertise in project and portfolio management, including cost, schedule, risk, and benefits tracking. 

• Deep understanding of Agile and hybrid delivery models and how PMs complement Product and Engineering teams. 

Transformation Orientation 

• Skilled at navigating complexity, driving change, and enabling new ways of working across multiple stakeholder layers. 

• Adept at balancing structure and flexibility to enable speed and accountability in delivery. 

People and Cultural Leadership 

• Experience leading diverse, high-performing teams and instilling a culture of collaboration and continuous improvement. 

• Strong executive presence and communication skills; able to influence without authority across senior levels. 

Required Skills 

• 10+ years of progressive experience in program/project management or enterprise transformation, with at least 5 years leading PMO or delivery teams. 

• Bachelor’s degree in business, technology, or related discipline. 

• Proven experience managing complex, cross-functional programs with both technology and organizational components. 

• Deep familiarity with Agile, hybrid, and waterfall methodologies; experience embedding PM roles within Agile environments. 

• Strong financial acumen and ability to link program delivery to budget, cost, and value realization outcomes. 

• Excellent communication, facilitation, and executive presentation skills. 

Preferred Skills 

• Advanced degree or PMP/Agile certifications (e.g., PMP, PgMP, SAFe, CSM, ACP). 

• Experience leading transformation PMOs within large, regulated enterprises or financial services firms. 

• Exposure to technology modernization, cloud migration, or AI-enabled transformation programs. 

• Experience implementing project portfolio management (PPM) platforms and dashboarding tools (e.g., Jira, Clarity, Power BI, Smartsheet). 

• Ability to apply data-driven insights to improve delivery performance and inform prioritization decisions. 

Success Measures (First 6–12 Months) 

• Delivered current-state assessment and future-state TMO vision endorsed by TDAV leadership. 

• Implemented standardized project governance, reporting, and delivery frameworks. 

• Improved project delivery predictability and stakeholder satisfaction. 

• Achieved measurable productivity or efficiency improvements in delivery outcomes. 

• Established TMO as a trusted enabler of transformation across Technology, Data, and AI. 

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