We are seeking a part-time Technology Trainer to help our staff and volunteers confidently use the technology and collaboration tools they rely on every day. You will work on an as-needed basis, delivering training at our headquarters and field offices across the country, remotely.
This role bridges the gap between IT capabilities and everyday user adoption. Training topics are diverse, so you will own the full cycle: finding existing curriculum (free or purchased) where it fits, building your own where it doesn't, and refining it based on what learners tell you. Just as important as presenting is listening: you will take time to hear users' questions, understand where they struggle, and adapt your training to meet them where they are.
Key responsibilities:
Deliver instructor-led training in person at headquarters and field offices, and virtually, plus self-paced options where appropriate.
Source training curriculum by evaluating free and commercially available courses, and recommending purchases where they offer the best value.
Design and develop custom curriculum for specialized or less common systems where no suitable off-the-shelf material exists.
Create training materials tailored to different skill levels, including guides, short videos, quick-reference cards, and e-learning modules.
Serve as a train-the-trainer for designated systems, preparing internal staff to teach others in their offices.
Partner with IT and department stakeholders to identify training needs tied to new system rollouts, migrations, and feature updates.
Listen actively to learners, capture their questions and pain points, and use that input to improve content and identify follow-up needs.
Hold office hours and on-site support sessions to troubleshoot common user issues and reinforce training.
Build and maintain a central library of how-to content, FAQs, and best practices.
Educate users on governance standards such as file naming conventions, permissions, and content lifecycle practices.
Track training metrics (attendance, satisfaction, and adoption) and report on program effectiveness and gaps.
Required qualifications:
Bachelor's degree in Information Technology, Instructional Design, Communications, or a related field, or equivalent experience.
2+ years of experience training end users on SharePoint Online or Microsoft 365 tools.
Strong working knowledge of SharePoint site structure, permissions, document libraries, and lists from a user's perspective.
Demonstrated experience sourcing, evaluating, and adapting third-party training content, and building curriculum from scratch.
Experience creating training content such as slide decks, job aids, and video tutorials.
Excellent presentation, facilitation, and active listening skills, with patience for learners at every skill level.
Ability to translate technical concepts into clear, non-technical language.
Comfort learning new systems quickly and teaching across a wide range of topics.
Ability to travel to office locations and to work a flexible, as-needed schedule.
Preferred qualifications:
Familiarity with instructional design principles and adult learning theory.
Experience with e-learning authoring tools (e.g., Articulate, Camtasia) or LMS platforms.
Microsoft certifications, such as Microsoft 365 Certified: Fundamentals or Teamwork Administrator Associate.
Experience delivering cybersecurity awareness or disaster recovery and business continuity training.
Experience with Power BI and Power Platform tools (Power Automate, Power Apps).
Experience training staff on healthcare, case management, or financial systems.
Experience running train-the-trainer programs.
Experience supporting a nonprofit or multi-site organization.
Numbers & Facts
Location
Boston, Massachusetts (Remote)
Salary
$50–$90
Skills
Adult Learningunmatched
Best Practicesunmatched
Case Managementunmatched
Communication Skillsunmatched
Content Developmentunmatched
Customer Acquisitionunmatched
Disaster Recoveryunmatched
Financial Systemsunmatched
Frequently Asked Questions (FAQ)unmatched
Healthcareunmatched
Identify Issuesunmatched
Information Technology & Information Systemsunmatched
Instructional Designunmatched
Internet Securityunmatched
Metricsunmatched
Microsoft Certificationsunmatched
Microsoft Product Familyunmatched
Microsoft SharePointunmatched
Needs Assessmentunmatched
Nonprofitunmatched
On Site Supportunmatched
Power BIunmatched
Program Evaluationunmatched
Staff Trainingunmatched
System Migrationunmatched
Team Playerunmatched
Technical Trainingunmatched
Train-the-Trainerunmatched
Training/Teachingunmatched
Training/Teaching Curriculumunmatched
Training/Teaching Materialsunmatched
Willing to Travelunmatched
eLearningunmatched
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