Job Locations US-MA-Boston | US-Remote

ID

2026-261902

Position Type

Full-Time

Job Grade

19

Department

0001-02442 Global Legal & Compliance, Exec Staff

Market

Corporate Center

Minimum Salary

USD $145,000.00/Yr.

Maximum Salary

USD $257,000.00/Yr.

Typical Starting Salary

$173,000 - $229,500

Recruiter

Roy Ruhling

Internal Application Deadline

10/2/26

Referral Bonus Eligible?

No

AI Transformation & Strategy exists to make AI a practical, embedded capability across Global Legal & Compliance, not an experiment on the side, but a core part of how we work, deliver, and create value for the enterprise. This pillar drives GL&C's ability to responsibly adopt, scale, and govern AI and emerging technologies in service of our 2030 vision: to serve as both a protector of the enterprise and an accelerator of Liberty Mutual's ability to win in the markets where we compete.

This role sits within the newly formed GL&C Data Office, under the Strategy, Intelligence & Integration organization, at a defining moment for GL&C and Liberty Mutual. The Transformation Lead will report to the GL&C Data Officer. They will connect AI strategy directly to data governance, analytics, product management, and knowledge management so that GL&C’s AI investments are grounded in trusted data, aligned to GL&C priorities, and built to compound over time.

The AI Transformation Lead will design GL&C's holistic AI strategy and roadmap to execution for 2030, focusing on the most critical AI value drivers for GL&C by quarterbacking initiatives that are highly complex, cross-functional, and cross-imperative. They will be responsible for effectively driving solutions to enable us to achieve our GL&C 2030 goals and productivity targets.

The Transformation Lead will effectively synthesize diverse perspectives into a cohesive and aligned AI Transformation strategy by bringing the right voices to the table, building mutual trust and strong relationships, and allowing for vigorous debate. They will drive a unified vision across senior leaders and key stakeholders inside and outside of the SBU, while ensuring initiatives are in alignment with strategic business priorities.

Ultimately, the Transformation Lead needs to leverage varying resources to build the plan and infrastructure that will turn strategy into reality, ensuring robust execution and outcome achievement. They will do so in partnership with key stakeholders – the GL&C Data Officer, aligned GL&C Technology Leader, newly formed GL&C Performance and Execution Team, Data Science, Product Owner and Learning and Development teams, the GL&C AI Big Rock Team, and other key stakeholders, as needed. The Transformation Lead will focus on advancing GL&C internal AI capabilities, building upon the significant foundational work completed and delivered to date by the GL&C cross-functional working team that was established in 2025.

Why This Role Matters:

GL&C is choosing to lead. We're not waiting for AI to happen to us. We are shaping how it transforms legal work at one of the world's largest insurers. This role is at the center of that effort. You will have the mandate, the executive sponsorship, and the opportunity to build something that changes how 1,700+ legal and compliance professionals work, and in doing so, help Liberty Mutual deliver on its purpose: to help people embrace today and confidently pursue tomorrow.

Job Responsibilities

Responsibilities of the AI Transformation Lead, include, but are not limited to, the following:

• 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.

Required Qualifications:

• 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

Preferred Qualifications:

• 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

Employees may apply for a new role after completing 12 months of employment in their current position.

Only open to US-based employees.

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