Head Learning Development Jobs in Maryland (NOW HIRING)

Why Join GEICO?
At GEICO, we offer a rewarding career where your ambitions are met with endless possibilities.
Every day we honor our iconic brand by offering quality coverage to millions of customers and being there when they need us most. We thrive on relentless innovation to exceed our customers' expectations while making a real impact on local communities nationwide.
Founded in 1936, GEICO is a member of the Berkshire Hathaway family of companies and one of the largest auto insurers in the United States. When you join our company, we want you to feel valued, supported, and proud to work here. That's why we offer the GEICO Pledge: Great Company, Great Culture, Great Rewards, and Great Careers.
GEICO is seeking a dynamic Manager, AI Learning and Development (L&D) to lead enterprise AI learning and enablement. The manager will scale AI literacy and adoption across our large, U.S.-distributed workforce, ensuring associates can use AI responsibly and effectively in their day-to-day work. It is a unique opportunity to design, develop and deliver high-impact learning experiences that build AI fluency at scale and help transform our workforce for the AI era. The manager will lead complex, cross-functional programs from design, development through execution in partnership with Technology, Communications, People, Operations, and business leaders.
Position Overview
The Manager, AI Learning and Development will lead end-to-end planning, coordination, and execution of enterprise AI learning and development initiatives. This role translates priorities into actionable roadmaps, aligns stakeholders across functions, and drives consistent, measurable outcomes tied to business goals. Success requires strong learning and development expertise, disciplined project management, partnership and the ability to shape practical, scalable AI enablement solutions that build workforce fluency and adoption.
Key Responsibilities

• Design and Deliver Scalable AI Learning Programs: Design, develop and deliver large-scale AI literacy and upskilling initiatives that reach employees at all levels. This includes creating and deploying blended learning experiences (workshops, webinars, e-learning modules, on-demand resources) to rapidly increase AI fluency and adoption across the enterprise.

• Project Management & Execution: Oversee end-to-end project management for AI learning and development projects, including goal setting, roadmaps, project planning, stakeholder coordination, timeline management, and post-program evaluation. Ensure on-time, high-quality delivery of AI learning programs that meet business needs at scale.

• Content Development & Curation: Work with subject matter experts (SMEs) to develop and curate AI-driven learning content (e.g., interactive workshops on using AI tools, job aids, prompt libraries, just-in-time learning support, etc.). Translate complex AI and machine learning concepts into accessible, practical lessons for non-technical audiences, emphasizing real-world applications in their roles.

• Facilitation & Hands-On Training: Facilitate engaging learning sessions - from live demos and hands-on training on generative AI tools (e.g., Microsoft 365 Copilot, ChatGPT Enterprise, LLM-based platforms) - to empower employees and champion transformation. Lead workshops and immersive training that demonstrate AI use cases and best practices, building confidence and enthusiasm.

• Cross-Functional Alignment: Ensure that AI learning initiatives adhere to enterprise guidelines and responsible AI governance policies. Coordinate closely with IT, governance, and internal teams to integrate AI usage standards into training content. Maintain alignment with the organization's overall AI strategy (e.g., working with the Head of AI L&D or digital transformation leaders) so that learning programs directly support broader AI integration goals.

Required Qualifications

• 5-7+ years of experience leading large-scale learning and development or talent/organizational development, tech enablement / transformation programs in a complex enterprise environment, with a track record of delivering measurable business results.

• Experience in AI-related and Tech Fluency L&D Roles in developing training curricula, enabling upskilling with AI tools and emerging technologies in a large-scale enterprise environment. Familiarity with generative AI applications (e.g., prompt engineering, ChatGPT or Microsoft Copilot) and understanding of how to integrate them into business workflows.

• Strong program and project management skills, including roadmap development, stakeholder alignment, risk management, and disciplined execution from concept through launch.

• Excellent facilitation, presentation, and communication skills, with the ability to make complex topics clear, practical, and engaging for a range of audiences, including senior leaders.

• Bachelor's degree in Business, Education, Organizational Development, Technology, or a related field, along with the ability to thrive in ambiguity, adapt quickly, and lead through change transformation in a fast-evolving environment.

Preferred Qualifications

• Experience in a large enterprise environment working on AI enablement, digital transformation, or technology adoption initiatives with proven skills in AI tools (e.g., Microsoft 365 Copilot, Claude) and enterprise learning platforms.

• Certification in AI or Program or Project Management (PMP, Agile, or equivalent).

• Background or certification in Instructional Design, Adult Learning theory, or Learning Experience Design for technology-related skills.

• Exposure to enterprise L&D platforms / tools, digital adoption platforms, and data analytics for learning (to track impact and adjust programs accordingly).

Why Join Us
This is a unique opportunity to shape AI enablement at GEICO by building practical, scalable learning solutions that strengthen workforce capability, accelerate enterprise transformation, and deliver measurable business impact. In this high-visibility role, you will help define how AI is adopted across the organization while growing your expertise in one of the fastest-evolving areas of learning and development.
#LI-EW1
Annual Salary
$97,375.00 - $172,200.00
The above annual salary range is a general guideline. Multiple factors are taken into consideration to arrive at the final hourly rate/ annual salary to be offered to the selected candidate. Factors include, but are not limited to, the scope and responsibilities of the role, the selected candidate's work experience, education and training, the work location as well as market and business considerations.
At this time, GEICO will not sponsor a new applicant for employment authorization for this position.
The GEICO Pledge:
Great Company: Protecting customers through life's twists and turns with innovation and integrity.
Great Careers:Personalized development programs, mentorship, and certification assistance.
Great Culture:Inclusive and collaborative culture rooted in shared success.
Great Rewards:Competitive pay, benefits, and flexibility to support your well-being and future.
The equal employment opportunity policy of the GEICO Companies provides for a fair and equal employment opportunity for all associates and job applicants regardless of race, color, religious creed, national origin, ancestry, age, gender, pregnancy, sexual orientation, gender identity, marital status, familial status, disability or genetic information, in compliance with applicable federal, state and local law. GEICO hires and promotes individuals solely on the basis of their qualifications for the job to be filled.
GEICO reasonably accommodates qualified individuals with disabilities to enable them to receive equal employment opportunity and/or perform the essential functions of the job, unless the accommodation would impose an undue hardship to the Company. This applies to all applicants and associates. GEICO also provides a work environment in which each associate is able to be productive and work to the best of their ability. We do not condone or tolerate an atmosphere of intimidation or harassment. We expect and require the cooperation of all associates in maintaining an atmosphere free from discrimination and harassment with mutual respect by and for all associates and applicants.