AI Workforce Enablement Lead

Markel•Chicago, IL

1d•$116,080 - $159,610•Onsite

About The Position

Join the U.S. & Bermuda Center for AI Enablement and play a key role in accelerating enterprise-wide AI adoption. In this role, you will help colleagues build confidence and practical skills to use AI in their daily work, supporting the rollout of training, tools, and resources aligned to enterprise standards. You’ll contribute to hands-on learning experiences, develop scalable enablement materials, and support communities of practice to drive engagement and adoption across the organization. This role also reinforces responsible and compliant AI use while gathering feedback and tracking adoption metrics to continuously improve programs.

Requirements

Experience helping people adopt new tools, technologies, or ways of working, with an understanding that successful change requires communication, patience, and reinforcement.
Comfort designing or delivering practical training or enablement, such as workshops, job aids, coaching, or learning sessions that help people apply new skills in their daily work.
Ability to explain new or complex topics as AI in clear, simple terms that make sense to a wide range of colleagues.
A collaborative mindset and the ability to build trust with teams, leaders, and front‑line colleagues while influencing change without direct authority.
Basic familiarity with AI and digital tools, with a focus on how they can responsibly support work rather than replace human judgment and alignment to enterprise-approved toolsets and platforms.
Awareness of the importance of responsible and compliant use, including knowing when to follow guidelines, escalate questions, or pause adoption.
Willingness to listen, gather feedback, and adjust training or enablement approaches based on what is working and what is not.
Curiosity and adaptability, with interest in learning alongside others as AI capabilities and business needs continue to evolve.
US Work Authorization required. Markel does not provide visa sponsorship for this position, now or in the future.

Responsibilities

Support the U.S. & Bermuda AI transformation by enabling organization‑wide adoption of AI, helping colleagues build confidence and practical capability to use AI in their daily work.
Contribute to the design and execution of an enterprise AI adoption program, including development of on‑demand learning resources, use case libraries, and clear, actionable guidance aligned to approved tools, platforms, and policies.
Help deliver hands‑on, project‑based learning experiences that focus on real work examples and practical application rather than classroom or theoretical instruction.
Support leadership mentoring and coaching efforts by helping articulate the “art of the possible” and reinforcing how AI can be used responsibly to improve outcomes.
Assist in building and sustaining communities of practice and superuser networks, enabling front‑line practitioners to share use cases, learn from one another, and accelerate adoption at scale, while promoting standard patterns and avoiding fragmented approaches.
Reinforce responsible and compliant use of AI by embedding safe‑use guidance, escalation paths, and governance expectations into training, communications, and enablement activities.
Gather and synthesize feedback from colleagues, superusers, and leaders to identify adoption barriers, learning gaps, and improvement opportunities, sharing insights with the broader AI Enablement team.
Support tracking and reporting on adoption and engagement metrics including usage, proficiency, and value realization, help assess progress, inform priorities, and continuously improve workforce enablement efforts.