Director, AI Transformation

Liberty Mutual InsuranceBoston, MA
2d$120,000 - $257,000

About The Position

The Director, AI Transformation within People, Purpose, & Brand (PP&B) is responsible for shaping and driving AI-enabled transformation across PP&B. As a core member of the PP&B AI Transformation Pod, this role plays a critical function in translating our AI ambition into tangible, measurable outcomes that enable teams to work better, smarter, and faster. Sitting at the intersection of strategy, technology, and execution, this role focuses on identifying, prioritizing, and delivering high-value AI opportunities across PP&B, while supporting responsible adoption, scalable delivery, and sustainable change. About the Role Reporting to the AI Transformation Leader for PP&B, this role serves as a key driver and orchestrator of AI initiatives and operates as an integral member of the AI Transformation Pod. You will help shape strategy, establish roadmaps and collaboration models, and lead cross-functional delivery of AI solutions, with focus on GenAI and agentic ways of working. Success in this role requires strong influencing skills, comfort navigating ambiguity, and the ability to drive momentum from concept through pilot and scale. You will partner closely with PP&B leaders, Technology, Data & Data Science, Legal, Global Compliance & Ethics, Change Management, and others to ensure AI initiatives are aligned to business priorities, delivered responsibly, and embedded into day-to-day ways of working. What Success Looks Like Clearly articulated and executed AI roadmap for PP&B, grounded in business value Implemented AI solutions that improve productivity, decision-making, and experience Clear governance and success metrics that enable responsible and repeatable delivery PP&B leaders confident in leveraging AI as part of how work gets done Experimentation and continuous improvement supported by disciplined execution

Requirements

  • 5+ years of experience across strategy, transformation, consulting, technology, or related fields, with progressive responsibility
  • 10+ years of experience across strategy, transformation, consulting, technology, or related fields, with progressive responsibility
  • Proven track record leading enterprise-scale transformation or strategic initiatives with measurable business impact
  • Strong strategic orientation with the ability to translate vision into executable roadmaps, plans, and outcomes
  • Demonstrated experience leading complex, cross-functional initiatives in large, matrixed organizations
  • Exceptional stakeholder management and influencing skills, with executive-ready presence and communication
  • Strong program and initiative management capabilities, including governance, prioritization, and performance tracking
  • Excellent written and verbal communication skills, with the ability to translate complex concepts into clear business narratives
  • Working knowledge of AI and emerging technologies, with the ability to assess opportunities, risks, and trade-offs
  • Ability to build fluency quickly in GenAI and agentic capabilities and articulate where they add value and where they do not
  • Demonstrated curiosity and learning mindset, with comfort experimenting with new tools and ways of working
  • Bachelor’s degree required; advanced degree preferred
  • Operates as a Director-level contributor within the AI Transformation Pod, influencing direction and driving execution in close partnership with the Pod Lead
  • Leads through influence, clarity, and strong judgment rather than formal authority
  • Brings executive presence and communication to complex, ambiguous challenges
  • Models collaboration, curiosity, and accountability while helping teams adopt AI-enabled and agentic ways of working
  • Builds credibility with leaders and peers through insight, pragmatism, and consistent delivery

Nice To Haves

  • Experience with HR transformations preferred
  • Experience leading or contributing to digital, analytics, or AI-enabled initiatives strongly preferred -- deep technical expertise not required

Responsibilities

  • Translate PP&B AI transformation priorities into clear roadmap and execution plan
  • Develop repeatable frameworks for business cases, success metrics, and KPIs to measure business value (e.g., ROI, productivity gains, experiential impact, etc.)
  • Monitor AI trends, tools, and capabilities, assessing relevance / applicability
  • Drive actionable programs and initiatives, ensuring disciplined execution from ideation through pilot and scale
  • Lead complex, cross-functional AI initiatives within PP&B, managing dependencies, risks, timelines, and outcomes
  • Partner with technology and business teams to embed GenAI and agentic capabilities into workflows and operating models
  • Act as trusted advisor to PP&B leaders on AI priorities, progress, risks, and opportunities, in close partnership with the AI Transformation Pod Lead
  • Facilitate prioritization, investment, and decision-making forums related to AI initiatives, driving alignment across stakeholders
  • Leverage pilots, proofs of concept, and rapid iteration to embed a culture of curiosity, experimentation, and continuous improvement
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