Technical Trainer - Technology and AI Enablement

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 the lead enterprise technology organization for the Commonwealth of Massachusetts. Charged with driving the ongoing alignment of business and technology across the Commonwealth’s Executive Branch, EOTSS oversees and manages the enterprise technology, digital infrastructure and services, as well as the Commonwealth Security Operations Center and an enterprise Standard Operating Environment that includes an information security and risk management framework for over 125 state agencies and over 43,000 state employees. We directly serve our constituents by providing digital services and tools that enable taxpayers, drivers, businesses, visitors, families and other citizens to do business with the Commonwealth in a way that makes every interaction with government easier, faster, and more secure.

Our Mission:

We provide technology leadership across the Commonwealth to enhance the quality of public service and foster positive community outcomes.

Role Overview:

We are seeking an experienced Technical Trainer in a contract role to support enterprise technology training, employee enablement, and adoption across a large, complex organization.

The initial area of focus will be supporting the enterprise-wide implementation and adoption of ChatGPT and AI Assistant capabilities. This role will help employees build the knowledge, confidence, and practical skills needed to use AI tools effectively and responsibly in their work.

Reporting through Human Resources, the Technical Trainer will work closely with business leaders, employees, technology teams, subject matter experts, and external vendors to assess learning needs and develop and deliver engaging, practical training experiences.

While AI enablement will be the initial priority, this role may also support training for other enterprise technologies and business process changes as needs evolve.

What You’ll Do:

Assess & Plan

• Partner with HR, business leaders, and employees to understand training needs, skill gaps, and employee readiness.
• Identify opportunities for enterprise-wide, role-based, and function-specific learning.
• Recommend training approaches based on employee needs, implementation priorities, and available resources.

Develop & Deliver Training

• Develop and facilitate engaging in-person, virtual, role-based, and use-case-focused training.
• Translate technical concepts into practical, accessible 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 AI 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 applicable expectations related to information security, data handling, and organizational policies.
• Gather feedback, identify adoption barriers, and recommend additional training or support as needs emerge.

Collaborate with Vendors & Partners

• Work with technology vendors and implementation partners when specialized product or training expertise is available.
• Leverage vendor-provided curricula, documentation, and train-the-trainer resources where appropriate.
• Coordinate and support vendor-led learning sessions.
• Adapt and supplement vendor training to reflect organizational policies, business processes, employee roles, and practical use cases.

What We’re Looking For:

• Demonstrated experience developing and delivering technical training for adult learners.
• Strong facilitation and presentation skills, including experience leading in-person and virtual learning sessions.
• Experience supporting technology implementations, technology adoption, or significant business process change.
• 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, subject matter experts, and/or 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 is strongly preferred. Familiarity with responsible AI practices, data privacy, information security, and enterprise AI adoption is also desirable.

All offers of employment into this position are conditional and subject to passing: a Massachusetts Criminal Background Check (CORI)

Work Location & Travel:

This role will support employees and learning activities in and around the Greater Boston area. The Technical Trainer is expected to work onsite as needed to facilitate, support, and host in-person training sessions, workshops, office hours, and other learning events.

The role requires flexibility to travel between work locations within the Greater Boston area based on training schedules and business needs. Some training, planning, and stakeholder engagement may also be conducted virtually.

What Success Looks Like:

The successful candidate will be a hands-on trainer and facilitator who is comfortable working across business and technical teams, quickly learning new technologies, and turning complex concepts into useful learning experiences.

They will bring curiosity, adaptability, strong communication skills, and a practical approach to helping employees adopt new tools and ways of working.