Senior Technology Training Specialist - STTS 26-10848

Senior Technology Training Specialist

Location: Annapolis, MD
Work Arrangement: Hybrid – 3 days remote / 2 days onsite
Duration: 5 years
Schedule: Monday–Friday, 8:00 AM–4:30 PM EDT

Position Overview

We are seeking a Senior Technology Training Specialist to develop and deliver technology training and supporting documentation for applications used within a large organizational environment.

The successful candidate will support commercially available and proprietary/customized applications, Microsoft Office/Microsoft 365 technologies, and specialized technical solutions. This role requires strong instructor-led training, instructional design, technical documentation, and stakeholder collaboration skills.

Key Responsibilities

• Plan, develop, and deliver hands-on instructor-led technology training for commercially available and proprietary software applications.
• Deliver training to individuals and groups with varying levels of technical proficiency.
• Apply adult learning principles to technology training and instructional design.
• Develop technical documentation, including:
  • Quick Reference Cards
  • Quick Reference Guides
  • User guides
  • Job aids
  • Web content
  • Other instructional materials
• Develop training videos and interactive or recorded training content.
• Create instructional design modules and learning materials.
• Collaborate with technical SMEs, business stakeholders, and application owners to translate complex technical concepts into effective training.
• Identify user challenges, knowledge gaps, and training needs.
• Determine appropriate training and documentation solutions based on identified needs.
• Manage training initiatives from planning and requirements gathering through development, delivery, evaluation, and completion.
• Manage multiple concurrent training initiatives, stakeholders, resources, and deadlines.
• Develop project plans, status updates, risk assessments, and deliverable updates for project leadership.
• Provide training and documentation support for Microsoft Teams, Copilot, OneNote, SharePoint, and Microsoft 365 applications.
• Ensure training materials remain accurate, consistent, user-friendly, and aligned with organizational requirements.
• Evaluate training effectiveness and incorporate feedback into future training and documentation.

Required Qualifications

• Bachelor's degree from an accredited university is required.
• Strong professional experience delivering technology and application training.
• Demonstrated experience conducting live instructor-led software training.
• Experience developing technical documentation to support software applications and business users.
• Strong understanding and practical application of adult learning principles.
• Experience developing software/application training rather than primarily soft-skills, HR, compliance, or general corporate training.
• Strong instructional design, communication, presentation, and organizational skills.
• Ability to manage multiple projects and deadlines simultaneously.
• Ability to work in a hybrid environment in Annapolis, Maryland, including regular onsite attendance.

Preferred Qualifications

• 5+ years of technology training experience.
• 3+ years of technical documentation experience.
• Experience with Microsoft 365 / Office 365, including:
  • Microsoft Teams
  • Microsoft Copilot
  • SharePoint
  • OneNote
  • Word
  • Excel
  • PowerPoint
  • Outlook
• Experience with instructional and content-development tools such as:
  • Camtasia
  • Articulate 360
  • Storyline
  • Rise 360
  • Vyond
  • Adobe Captivate
  • Snagit
• Experience developing eLearning and interactive instructional content.
• Video-based training development experience.
• Quick Reference Guide and job-aid development experience.
• Training project management experience.
• Experience collaborating with technical and business Subject Matter Experts (SMEs).