Director, Enterprise AI Learning, Governance and Innovation

The Hartford•Boston, MA

1d•$128,000 - $192,000•Hybrid

About The Position

We are seeking an experienced Director, Enterprise AI Learning, Governance, and Innovation to join our Enterprise Learning team. Reporting to the Assistant Vice President, Enterprise Learning, this leader will partner closely with colleagues across the enterprise to shape and deliver our foundational AI learning strategy. The role includes identifying AI-first skill development needs, sourcing and tailoring learning solutions through The Hartford Learning Academy, and helping employees build the skills to use AI effectively in their work. In addition, this person will collaborate with learning leaders across The Hartford’s Learning Collaboration Team to establish governance standards and processes that improve the efficiency, consistency, and impact of learning tools and practices. This role will also stay at the forefront of innovation by identifying, testing, and scaling new state of the art learning design and delivery approaches across the enterprise. The position is based in our Hartford, CT Home Office, though candidates based elsewhere may also be considered.

Requirements

8+ years leading enterprise learning, talent, or enablement programs, including designing learning strategies for diverse, often non-technical audiences; experience in financial services or another highly regulated industry is a plus.
Strong fluency in AI concepts and practical applications, with the ability to translate them into simple, actionable learning for the business.
Experience establishing governance and operating models for learning tools and processes, including standards, templates, prioritization, quality assurance, and continuous improvement.
Strong program and project management skills, with a track record of leading multiple workstreams and stakeholders in a fast-paced environment.
Experience evaluating, piloting, and scaling learning technologies and AI-enabled tools, including building business cases, defining success metrics, and partnering with IT, Security, Legal, and Procurement.
Data- and outcomes-oriented mindset, with experience measuring learning impact beyond completion, including proficiency, confidence, behavior change, adoption, and performance outcomes.
Excellent executive communication, stakeholder management, and change leadership skills, with the ability to influence senior leaders, build trusted partnerships, and drive adoption across a decentralized learning community.
Bachelor’s degree or equivalent practical experience.

Nice To Haves

If based outside Hartford, willing and able to travel as needed, up to approximately 20% of the time and potentially more during the first three to nine months.

Responsibilities

Lead an enterprise-wide AI literacy strategy that builds confidence, practical judgment, and reinforces responsible AI use across the organization.
Source and tailor skills-based AI learning that supports The Hartford’s AI-First culture.
Lead quarterly delivery of enterprise AI literacy learning, integrated with The Hartford Learning Academy.
Consult with Learning Academy team and Business Advisory Council members to understand enterprise AI learning needs, adoption barriers, and emerging capability gaps.
Collect, synthesize, and interpret learner feedback, skills survey data, and engagement metrics to assess impact and learning transfer.
Deliver executive-ready insights on participation, outcomes, and trends to inform leadership decisions and future learning innovation.
Translate learner insights into recommendations that inform future Learning Academy innovation.
Establish clear governance, standards, and operating rhythms that help learning teams use shared AI tools and processes consistently, effectively, and with appropriate controls.
Establish enterprise governance for learning design, delivery tools, and related metrics.
Oversee Learning Academy program operations and governance across learning platforms (e.g., Workday, ELLE, approved tools).
Provide input into learning upskilling for enterprise learning professionals.
Support adoption of governance through playbooks, office hours, coaching, and community practices that reduce duplication and improve consistency.
Continuously assess emerging AI-enabled learning capabilities, run focused pilots, and scale solutions that improve learner experience, speed to skill, and measurable outcomes.
Share pilot results to support strong business decisions and broader adoption.
Stay current on learning technology trends, AI-enabled tools, and delivery innovations, identifying opportunities to improve scale, efficiency, and learner experience.
Assess AI learning tools and vendors for fit, value, and risk posture, including solutions such as content generation, adaptive learning, coaching and role-play, and skills analytics.
Design and execute pilots with clear hypotheses, success metrics, and implementation plans; partner with IT/Security/Procurement/Legal as needed.
Evaluate pilot results and recommend scale/stop/iterate decisions; build adoption and change plans for scaled solutions across the learning community.
Share learnings and reusable standards with the Learning Collaboration Team to help embed innovation into the operating model.