Director, Transformation Management Office (Technology)

AAA Life Insurance Company•Livonia, MI

16h•Hybrid

About The Position

We need an ambitious, curious leader to become a Transformation Leader on the Technology Team to help drive the biggest change in the company’s history. The Opportunity – Why Join Are you ready to redefine how an entire industry engages with customers? At AAA Life we leverage technology to put human connection at the heart of what we do. If you are someone who thrives on purpose and wants to make a tangible difference in people’s lives when it matters most, then join AAA Life who has the unique ability to access tens of millions of existing AAA customers powered by the strength of one of America’s most trusted brands. We have embarked on a mission to double in size - Becoming one of the largest providers in the US. These facts showcase why we're the right choice: On purpose: a leading professional services firm found that the commitment, empathy and dedication of employees at AAA Life was the highest across a benchmark of top US companies On growth: we have the privilege to offer our products to tens of millions of Americans that are proud members of AAA On making a difference: we serve Americans by delivering life insurance products that make a true difference for families during their hardest times, not wealth management instruments (more details on this during the interview) On culture: USA Today named us 2025 top workplace nationwide. We believe the job of an insurance company is to do good. Our mission is to help our members during what is often the hardest times in their lives. We pick up the phone to people who have lost loved ones and offer our genuine support. That is why we will always put human connection at the heart of what we do - always being there to talk to our members person to person. We believe the job of an insurance company is to pay out. That is what insurance is for. Most of our members have real life policies - policies that bring peace of mind during life, and genuine support in the event of death. We are not here to chase the super-rich with annuities and wealth management products. AAA has been one of the most trusted names in America because it believes in providing the services that middle class Americans need. The Next Phase Our mission is to provide those services for as many people as we can. To achieve that we need to evolve. We need to boldly embrace innovation and technology. Your leadership will help us deliver on our mission together and achieve our transformation. At AAA Life, empathy and progress go hand in hand, creating a culture where bright ideas flourish and meaningful impact grows. If you are drawn to an environment that values purpose as much as potential, we invite you to join us. Because here, being there for people isn’t just a promise—it is our driving force.

Requirements

10+ years of experience leading or governing large-scale technology or enterprise transformations, with accountability for delivery and business outcomes
15+ years of experience operating at the intersection of technology project portfolio delivery, governance, and financial oversight
Experience driving significant business value through technology delivery, ideally within the insurance or broader financial services industry
Experience coaching Agile and DevOps best practices in legacy technology environments
Strong financial acumen, including experience supporting investment prioritization, funding trade-offs, and value tracking
Understanding of modern technology, data, and product operating models, including platform and legacy modernization
Experience driving accountability and course correction across matrixed organizations, including challenging leaders and plans when outcomes are at risk

Nice To Haves

Relevant professional certifications (e.g., PMP, SAFe SPC / Leading SAFe) are highly beneficial, with the ability to apply those disciplines in complex transformations

Responsibilities

Own and operate the Transformation Management Office (TMO), including management of the TMO team
Accountable for business value tracking, ensuring benefits realization is measured, reported, and actively managed alongside delivery, with corrective action taken when expected value stalls
Own transformation budget tracking and recommend funding priorities and reallocations, within guardrails agreed upon with the VP, Technology
Partner with Finance to drive investment prioritization, funding trade-offs, and capacity reallocation recommendations
Align transformation and technology project delivery within the TMO to provide a single, clear roadmap and consistent reporting
Lead transformation governance forums to review progress, confirm next steps, and surface, prioritize, and drive resolution of delivery risks and issues
Oversee change management, including regular communication with key business and technology stakeholders to ensure transparency and alignment
In collaboration with other technology leaders, drive the shift from a project-centric delivery model to a product- and platform-centric model including broader adoption of agile methodologies and DevOps best practices
Accountable for transformation delivery health across workstreams, including schedule confidence, risk and issue exposure, dependency resolution, sequencing decisions, and corrective action
Ensure consistent application of execution cadence, escalation discipline, and accountability