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.
#LI-TL2
Pay Transparency
Salary Range: $180,500-$258,000
Overtime eligible: Exempt
Discretionary bonus eligible: Yes
Sales bonus eligible: No
Actual base salary will be determined based on several factors but not limited to individual's experience, skills, qualifications, and job location. Additionally, employees are eligible for an annual discretionary bonus. In addition to base salary, employees may also be eligible to participate in an incentive program.
Company Overview
At New York Life, our 180-year legacy of purpose and integrity fuels our future. As we evolve into a more technology-, data-, and AI-enabled organization, we remain grounded in the values that drive lasting impact.
Our diverse business portfolio creates opportunities to make a difference across industries and communities-inviting bold thinking, collaborative problem-solving, and purpose-driven innovation. Here, you'll find the rare balance of long-standing stability and forward momentum, supported by an inclusive team that honors tradition while embracing progress.
As a Fortune 100 mutual company, we offer a place to grow your skills, contribute to meaningful work, and deliver solutions that matter. Your ideas drive what's next, and your growth powers it.
Our Benefits
We provide a full package of benefits for employees - and have unique offerings for a modern workforce, including leave programs, adoption assistance, and student loan repayment programs. Based on feedback from our employees, we continue to refine and add benefits to our offering, so that you can flourish both inside and outside of work.Click hereto discover more about our comprehensive benefit options or visit our NYL Benefits Site.
Our Commitment to Inclusion
At New York Life, fostering an inclusive workplace is fundamental to who we are and how we serve our communities. We have a longstanding commitment to creating an environment where individuals can contribute their best and succeed together. This foundation is rooted in our core values of humanity and integrity, ensuring that every employee feels valued and supported. By embracing a broad range of perspectives and experiences, we achieve greater success and fulfill our promise of providing financial security and peace of mind to families across all communities. Click here to learn more about New York Life's leadership in this space.
Recognized as one of Fortune's World's Most Admired Companies, New York Life is committed to improving local communities through a culture of employee giving and volunteerism, supported by the Foundation. We're proud that due to our mutuality, we operate in the best interests of our policy owners. To learn more about career opportunities at New York Life, please visit the Careers page of www.NewYorkLife.com.
Visit our LinkedIn to see how our employees and agents are leading the industry and impacting communities.
Visit our Newsroom to learn more about how our company is constantly evolving to meet our clients' and employees' needs.
Job Requisition ID: 92817
Top Skills
What We Do
At New York Life, our 180-year legacy of integrity, mutuality, and financial strength fuels a future defined by bold transformation.
As the largest mutual life insurance company in the U.S., we operate on behalf of our policy owners—not shareholders. That structure allows us to take a long-term view, investing in people, purpose, and innovation that endures.
Guided by a clear enterprise vision to become a technology-, data-, and AI-powered company, we’re modernizing our platforms, rearchitecting experiences, and embedding intelligence across our products and services.
Our mission has always been about helping people through life’s most meaningful moments. Today, technology is amplifying that mission—enabling us to serve clients, advisors, and communities in more personalized, proactive ways.
With a diversified business portfolio spanning insurance, investments, retirement, group benefits, and direct-to-consumer offerings, New York Life delivers the stability of a Fortune 100 company with the agility of one that’s continuously evolving.
We’re powered by a values-led culture, inclusive teams, and a shared belief that when our people thrive, so does our company. Here, tradition fuels momentum—and your ideas, energy, and growth power what’s next.
Why Work With Us
New York Life is transforming from the inside out—blending 180 years of trust with the velocity of innovation. What makes us different is our culture: grounded in integrity, humanity, and shared success—values that show up in how we work, lead, and grow. If you want a place where innovation has purpose—build what's next with us.
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