Transformation Strategy Lead

Guardian Life Insurance•Boston, MA

1d•Hybrid

About The Position

The Transformation Strategy Lead, Group Benefits is a critical role responsible for orchestrating and executing the company's most pivotal, large-scale transformation initiatives with a strong emphasis on AI integration and innovation. This individual will operate at the nexus of strategy, execution, and implementation, playing a pivotable role in shaping the future of Guardian Life through intelligent automation and data-driven decision-making. The Transformation Strategy lead sets strategy, defines the transformational roadmap leveraging AI capabilities, and drives execution through meticulous, hands-on delivery of complex initiatives. This role requires expertise in identifying opportunities for AI augmentation across business processes, implementing AI-powered solutions, and ensuring responsible AI governance throughout the transformation journey. Reporting to the Head of Transformation & AI Strategy, Group Benefits, this individual will lead through influence, guiding cross-functional teams in a matrixed environment to deliver foundational changes that reshape our business processes, technology platforms, and competitive positioning.

Requirements

7+ years of experience in management consulting and/or in a business operations, strategy, finance, or product role
2+ years of hands-on experience working with AI technologies, either implementing AI solutions or leading AI-enabled transformation initiatives
Excellent analytical and problem-solving skills with a history of hands-on detail-oriented work
Demonstrated business acumen with ability to see “big picture” and to prioritize
Strong communication and listening skills; able to convey important messages in a clear and compelling manner
Organizational savviness with ability to build relationships with senior executive leadership and influence with sense of urgency to ensure deadlines are met
Strong excel and PowerPoint skills with the ability to synthesize information related to key priorities and translate into a compelling narrative
Must be legally authorized to work in the United States, without the need for employer sponsorship.

Nice To Haves

Insurance industry expertise preferred, with understanding of Group Benefits products and regulatory environment

Responsibilities

Develop complex transformation roadmaps and delivery timelines that incorporate AI capabilities and identify opportunities for intelligent automation across Group Benefits operations
Evaluate and recommend AI tools and platforms (such as Microsoft Copilot, OpenAI APIs, Claude, or industry-specific AI solutions) to enhance transformation initiatives
Design AI implementation strategies that balance innovation with risk management and regulatory compliance in the insurance industry
Lead cross-functional teams, balancing forming alliances and driving results for Group Benefits most strategic initiatives while championing AI adoption
Facilitate AI literacy and capability building across teams, ensuring stakeholders understand both the potential and limitations of AI technologies
Partner with data science and engineering teams to translate business requirements into AI-powered solutions
Prepare and coordinate strategy documents, business plans, and presentations for Board, Quarterly and Monthly Business Reviews, and other Group Leadership meetings using AI-assisted content creation tools
Create compelling data visualizations and narratives using AI-enhanced analytics platforms
Develop relationships with key internal and external stakeholders to facilitate and drive critical projects, ensuring alignment and effective collaboration