Director II IC, Product Analysis

It's an incredibly exciting — and pivotal — time to join the Auto Product organization at Liberty Mutual. We are amid one of the most ambitious transformations in the company's history, rebuilding our Personal Lines Auto product and policy administration system from the ground up on a modern Guidewire Cloud platform. At the same time, we are continuing to deliver against our current Win Now business priorities — managing the complexity of running significant workstreams in parallel while keeping our eye on a clear end zone: a June 2027 Release 1 launch that sets the foundation for how Liberty Mutual writes and services auto insurance for years to come.

We are seeking an exceptional strategic operator for the Auto Product Management & Execution Organization. This leader will sit at the center of Frontier and Win Now — driving alignment across priorities, leading resource strategy, and ensuring that complex program information is translated clearly so the organization can digest it and execute against it. This is a role for someone who makes the people and work around them sharper, faster, and better aligned.

The ideal candidate is a strategic thinker who executes without ego — someone who can hold the long view while getting things done in a large, matrixed organization, and who understands that influence built on insight and credibility moves programs forward.

Map and manage the dependencies between Win Now work and future program scope, ensuring the organization is sequencing work intelligently, understanding decision impacts and not creating technical or process debt that blocks downstream delivery.

• Maintain a living view of cross-program dependencies — what today’s work enables or constrains for tomorrow
• Surface dependency risks to leadership before they become blockers
• Partner with domains and technology to sequencing decisions across PI cycles
• Ensure scope trade-off decisions are made with full awareness of downstream impact

Drive strategic direction regarding execution pathways. Manage contractor engagements and ensure optimization of workforce for Win Now and Frontier. Ensure resources are deployed effectively, and the portfolio is appropriately staffed against its priorities.

• Create recommendations on staffing ecosystem across Win Now and Frontier with respect to business and product owner resources
• Identify gaps and optimization opportunities across the resource portfolio
• Partner cross functionally to ensure long term strategy developed and accountability metrics followed through on
• Ensure resource decisions are connected to program priorities

Own the development of strategic projects ensuring that complex program information is translated into clear, compelling narratives for senior leadership and cross-functional audiences.

• Lead the development of presentations and program updates
• Translate complex delivery and product information for various audiences
• Drive the completion of strategic communications across the leadership team
• Ensure materials reflect a consistent, accurate, and well-framed view of the program status and direction

You bring

What that looks like here

Strategic thinking with operational discipline

You can hold the long view while also getting things done. You don’t just identify problems — you build the structure to solve them.

Experience in large-scale program environments

You understand how complex delivery programs work — dependencies, sequencing, resource constraints, and the gap between plan and reality.

Workforce and resource planning experience

You have managed or supported FTE and contractor planning, and you understand how to connect decisions to strategic priorities.

Executive communication skills

You write and structure clearly. You can take a complex, messy situation and produce a narrative that an audience can act on.

Comfort operating without authority

You influence through insight and credibility, not title. You get things done in a matrixed environment.

Insurance or financial services experience

Familiarity with Personal Lines Auto, policy administration, or a regulated product environment is a meaningful plus.

Guidewire or SAFe delivery familiarity

Experience in an Agile or SAFe delivery environment, or with Guidewire implementations, accelerates your impact — though it is not required.