AI Enablement Trainer for Enterprise Teams

Executive Office of Technology Services and Security; Boston (MA); On-site; USD 90,000 - 120,000; Full time

Job summary

The Executive Office of Technology Services and Security (EOTSS) is seeking an experienced Technical Trainer for a contract role to support enterprise technology training, employee enablement, and adoption across a large organization in the Greater Boston area.

The initial focus will be on onboarding ChatGPT and AI Assistant capabilities, translating complex concepts into practical training, delivering in-person and virtual sessions, and collaborating with HR, business leaders, and technology

Qualifications

• Demonstrated experience developing and delivering technical training for adult learners.
• Strong facilitation and presentation skills for in-person and virtual sessions.
• Experience supporting technology implementations or significant business process changes.
• Ability to translate technical concepts into clear, practical instruction for non-technical audiences.
• Experience developing role-based training, job aids, and other learning resources.
• Strong stakeholder management and collaboration skills.
• Experience working with business leaders, technical teams, SMEs, and external vendors.
• Strong organizational and project coordination skills with the ability to work independently across multiple priorities.
• Experience with ChatGPT, generative AI, AI assistants, Microsoft Copilot or similar technologies.

Responsibilities

• Partner with HR, business leaders, and employees to understand training needs, skill gaps, and readiness.
• Identify opportunities for enterprise-wide, role-based, and function-specific learning.
• Recommend training approaches based on employee needs, implementation priorities, and resources.
• Develop and facilitate engaging in-person, virtual, role-based, and use-case-focused training.
• Translate technical concepts into practical learning experiences for employees with varying levels of technical proficiency.
• Create supplemental learning resources, including presentations, job aids, FAQs, exercises, demonstrations, and self-service materials.
• Facilitate workshops, office hours, refresher sessions, and other learning events to support ongoing adoption.
• Support foundational training for ChatGPT and AI Assistant capabilities.
• Partner with business areas to identify relevant use cases and role-specific learning needs.
• Reinforce responsible AI practices, including data handling and security.
• Gather feedback, identify adoption barriers, and recommend additional training or support as needs emerge.
• Collaborate with vendors and partners; leverage vendor curricula and train-the-trainer resources.
• Coordinate vendor-led learning sessions and adapt training to reflect policies, processes, and roles.

Job description

The Executive Office of Technology Services and Security (EOTSS) is seeking an experienced Technical Trainer for a contract role to support enterprise technology training, employee enablement, and adoption across a large organization in the Greater Boston area.

The initial focus will be on onboarding ChatGPT and AI Assistant capabilities, translating complex concepts into practical training, delivering in-person and virtual sessions, and collaborating with HR, business leaders, and technology