Ai Transformation Lead - Global Legal & Compliance

Libertymutual; Boston (MA); On-site; USD 180,000 - 280,000; Full time

Job summary

Liberty Mutual Group is seeking a senior leader to define and own GL&C's AI strategy, crafting a multi-year roadmap that ties AI investments to the 2030 productivity glidepath and the work-evolution decision engine. You will identify interdependencies, resources, and risks while guiding governance and pilot-to-production efforts.

You will collaborate with Legal, Technology, and Data Officers to scale AI across daily workflows, ensuring security, trust, and measurable ROI.

Qualifications

• Experience defining and owning AI strategy and multi-year roadmaps for complex organizations.
• Proven ability to evaluate and advance AI tools with business rigor.
• Design and implement AI governance frameworks including responsible AI principles.
• Strong partnership skills with senior leaders, domain experts, and technical teams.
• Experience moving AI projects from pilots to production at scale.
• Ability to align AI investments with enterprise strategy and risk appetite.
• Familiarity with insurance industry, regulatory environments, or enterprise risk management.
• Hands-on experience with gen AI tools, LLMs, and agentic AI architectures.

Responsibilities

• Define and own GL&C's AI strategy and multi-year roadmap linked to the productivity glidepath and 2030 vision.
• Evaluate and advance AI tools, building a governance process to pilot and scale high-value AI solutions.
• Embed AI into daily workflows and delivery models in partnership with Performance & Execution.
• Develop ROI and business value measurement framework for AI usage across use cases.
• Collaborate on architecture to bridge business needs with technology and data.
• Establish internal guardrails, quality standards, and risk management for AI adoption.
• Build AI fluency across GL&C with L&D and Talent teams; measure adoption and competence.
• Align GL&C’s AI investments with Liberty's broader AI strategy and governance.

Skills

AI strategy

Digital transformation

Legal tech

Executive stakeholder management

Ambiguity navigation

Communication

Generative AI

Data Office collaboration

Job description

Responsibilities

• Defining and owning GL&C's AI strategy and roadmap — building and maintaining a clear, prioritized, multi-year AI roadmap that connects AI investments, including existing and future agentic workflow use cases, to the work evolution decision engine, practice group needs, and the $60M productivity glidepath underpinning GL&C's 2030 vision, while proactively identifying interdependencies, resource needs, and delivery or budget risks across the portfolio
• Evaluating and advancing AI tools for deployment — developing an efficient pipeline and governance process to identify, vet, pilot, and scale high-value GenAI and agentic AI tools, including advanced legal AI, that align with GL&C priorities and LMG's 2030 strategy, and moving promising pilots to production with rigor and speed
• Embedding AI into how GL&C works — moving AI from isolated experiments to a reliable, secure, and measurable part of GL&C's daily workflows and delivery models, partnering closely with Performance & Execution so teams work faster and produce higher-quality work
• Measuring and scaling AI impact — developing a framework to measure ROI and business value from AI usage across existing and new use cases, and driving the organizational shift from Level 1 everyday AI experimentation to Level 2 supercharging work on the LMG AI maturity curve
• Diving deep into the technical architecture — partnering with the team on solutioning that advances GL&C's future-state vision and closes gaps between business and technology
• Governing AI adoption responsibly — establishing the department's internal guardrails, quality standards, and risk management frameworks that allow GL&C to move fast without compromising integrity, accuracy, or trust
• Building AI fluency across GL&C — partnering with the newly formed GL&C Learning & Development function and Talent Team to establish baseline AI proficiency and target skill levels, roll out core education, and track adoption and competency metrics
• Connecting GL&C to the enterprise AI ecosystem — aligning GL&C's AI investments with Liberty's broader technology and AI strategy, Data Officers across other functions, and enterprise-wide governance frameworks

This role requires someone who can think strategically and execute operationally — who is equally comfortable presenting an AI roadmap to the Chief Legal Officer and rolling up their sleeves to run a pilot with a litigation team. The ability to influence a diverse range of stakeholders will be critical to success in the role.

Requirements

• 8+ years of experience in AI/technology strategy, digital transformation, legal technology, or a related field — with a track record of moving AI from concept to scaled adoption in complex organizations
• Demonstrated ability to evaluate emerging technologies with business rigor — separating real potential from noise and building credible business cases
• Experience designing and implementing AI governance frameworks, including responsible AI principles, quality standards, and risk management protocols
• Strong partnership skills — the ability to build trust and credibility with senior leaders, domain experts, and technical teams simultaneously
• Experience leading through ambiguity — building new capabilities where playbooks don't yet exist
• Excellent communication skills — the ability to translate complex AI concepts into clear, actionable language for legal professionals, business leaders, and technical audiences
• Experience in legal operations, legal technology, Data Science or professional services environments
• Familiarity with the insurance industry, regulatory environments, or enterprise risk management
• Hands-on experience with generative AI tools, large language models, and agentic AI architectures
• Experience working within or alongside a Data Office, analytics function, or enterprise technology organization
• Understanding of legal service delivery models, including in-house legal departments, managed legal services, and legal process outsourcing