Director / Senior Director, Strategy & Alignment

We are embarking on a multi-year transformation to simplify and modernize our business and technology. This transformation will be complex, challenging, and exciting, requiring all functions in the U.S Retail Market (USRM) to come together. Given the nature of the transformation, we require top notch talent with the skills, experience, and resilience to drive this work forward.   

Transformation Team:  

The Transformation team is accountable for driving work to achieve our north-star vision of both business and tech simplification.  

The team is accountable for:  

• Driving Transformational Change: responsible for the success and momentum of the overall program 

• Defining Program Vision: Articulating outcomes, scope, timelines and milestones   

• Driving Decision-making: Identifying key decisions and intentionally partnering with and influencing leaders at all levels to make clear decisions at the right pace 

• Experience and Change Management: Drive experience and change management efforts  

• Creating Clarity: Developing program management and communication tools that foster shared understanding, maintain momentum, and ensure transparency. 

The role:  Director / Senior Director, Strategy & Alignment 

We are looking for a high-performing individual contributor to join the Transformation team as a Transformation Lead aligned to the USRM overall strategies.  

The core accountabilities of the role will include:  

• Driving the Success by intentionally partnering with Business, Solutions, and Technology teams to drive transformative change 

• Driving Clarity by seamlessly connecting and influencing at various levels of workstreams and governance to track delivery, ensure accountability and challenge the status quo 

• Using judgment to move forward by continually evaluating progress vs. outcomes, flagging issues or risks, and recommending or implementing necessary adjustments or escalating as appropriate  

• Direct responsibility for select workstreams that lack a singular business leader such as Roadmap Sequencing (across line of business, channel, new vs. renewal business) Holistic Experience Mapping, Setting and Tracking OKRs, Organizational Change Management, and others TBD as the program evolves 

• Agency – Demonstrated ability to take ownership and lead complex strategic initiatives, demonstrating self-confidence and resilience navigating challenges and driving results. 

• Autonomous and Agile Work Style: Experience working independently in dynamic, fast-paced environments, adapting swiftly to changing circumstances. 

• Comfort with Ambiguity: Strong decision-making skills in uncertain environments; ability to synthesize incomplete information into actionable insights. 

• Influential Communication Skills - Expertise engaging with stakeholders at all organizational levels, effectively communicating ideas and driving influence. 

• Strategic Analytical Skills - Capacity to analyze complex business questions, create structured frameworks for addressing them, and drive cross-functional teams towards alignment on recommendations. 

• Execution Experience – Demonstrated success leading and executing large-scale business and/or technology initiatives with measurable outcomes. 

• Cross-Functional Experience – Experience working in multiple functions or business units leading to creating cross-cutting awareness of interconnectivity across the insurance value chain  

• Challenger mindset – Demonstrated comfort asking questions, challenging assumptions, and offering alternative perspectives to push teams towards the optimal answer for the organization 

This is a salary range posting, and we may fill as a Director or Senior Director, Strategy & Alignment depending on candidate demonstrated experiences and skillsets.