Senior Training & Development Specialist (M365 & Teams Services)

Dev TechnologyReston, VA
$80,000 - $130,000Remote

About The Position

Dev Technology Group is seeking a Training & Development Specialist (M365, Purview & Teams Services) to support enterprise user enablement, training development, and documentation for Microsoft 365 within a large federal environment. This role supports the adoption of Microsoft 365 G5 capabilities, with a focus on Microsoft Purview (e.g., Sensitivity Labels, Data Loss Prevention, retention policies) and the enterprise rollout of Microsoft Teams Phone. This position helps translate complex technical capabilities into clear, actionable guidance for end users and support staff, supporting adoption of compliance-driven behaviors such as labeling, secure sharing, and voice/calling capabilities in Teams. The role works closely with engineering, compliance, and operations teams to align training with real-world system configurations and mission needs.

Requirements

  • A Bachelor’s degree and a minimum of 3 years of related professional experience.
  • Experience supporting training development, documentation, or user enablement for enterprise systems.
  • Experience creating job aids, knowledge articles, and instructional materials for end users and support teams.
  • Strong ability to translate technical concepts into clear, user-friendly content.
  • Experience supporting enterprise software adoption or rollout efforts.
  • Excellent written communication, organization, and attention to detail.
  • Ability to collaborate effectively with both technical and non-technical stakeholders.
  • US citizenship required.
  • Must be able to obtain and maintain a DHS Public Trust clearance.

Nice To Haves

  • Experience supporting Microsoft 365 environments, including SharePoint, Teams, and OneDrive.
  • Familiarity with Microsoft Purview concepts, such as Sensitivity Labels, Data Loss Prevention (DLP), retention, and records management.
  • Experience supporting Teams Phone or enterprise voice rollouts.
  • Experience supporting federal or highly regulated environments (e.g., GCC/GCC High).
  • Familiarity with organizational change management (OCM) principles and adoption strategies.
  • Experience with content management and knowledge platforms (e.g., SharePoint, Confluence, Jira).
  • Experience delivering live or virtual training sessions.
  • Experience supporting an enterprise technology rollout impacting 1,000+ users.

Responsibilities

  • Develop and maintain training materials, job aids, and user documentation for Microsoft Purview capabilities (DLP, Sensitivity Labels, retention, secure sharing) and Microsoft Teams and Teams Phone (calling features, voicemail, call handling, devices).
  • Support enterprise G5 adoption efforts by creating content that drives user understanding of data classification and labeling expectations, and secure collaboration practices across SharePoint, Teams, and OneDrive.
  • Create and maintain Tier 1 and Tier 2 support documentation, including troubleshooting guides and FAQs.
  • Collaborate with technical teams to translate system configurations and policies into user-friendly guidance.
  • Support organizational change management (OCM) activities, including communication campaigns and training rollout planning.
  • Develop role-based training content tailored to different user personas (e.g., general users, power users, leadership, support staff).
  • Assist with training delivery, including live sessions, recorded content, and self-service materials.

Benefits

  • Generous and flexible time-off policy
  • Flexible work schedules and telework options, including remote work availability for eligible projects
  • Career development opportunities including a mentorship program, technical and management training through Dev University, hands-on learning through DevLab, tuition reimbursement, and paid training opportunities
  • Industry-leading benefits including a choice of two health plans that include dental and vision, flexible spending account, commuter benefits, life insurance, and more
  • 401K matching with a 5% matching contribution
  • Regular team and company social events including our annual party, happy hours, fitness challenges, and more
  • A focus on community engagement including company wide support activities, employer match for donations, and time off for volunteer efforts
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