Ai Transformation Lead - Global Legal & Compliance
Job in
Boston, Suffolk County, Massachusetts, 02298, USA
Listing for:
Libertymutual
Full Time
position
Listed on 2026-11-07
Job specializations:
-
IT/Tech
AI Business & Operations, AI Engineer (Applied/Software), AI Evaluation
Job Description & How to Apply Below
- 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
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