Senior Training & Development Specialist (M365 & Teams Services)

Dev Technology • Reston, VA

18h • Remote

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. This role serves as a contributor supporting training development, user enablement, and documentation efforts for Microsoft 365 services. You will develop and maintain training materials and supporting documentation across Microsoft 365 workloads, including Purview compliance features and Microsoft Teams Phone capabilities. Responsibilities include creating user-focused content that promotes understanding of data classification, secure collaboration practices, and enterprise communication tools. You will collaborate with technical teams to translate system configurations, policies, and requirements into clear, accessible materials for a variety of audiences. You will also support organizational change management activities, training rollout efforts, and assist with delivery of training through multiple formats, including live sessions and self-service resources. This role provides the opportunity to directly influence how users adopt and effectively use Microsoft 365 services across the enterprise. You will play a key role in enabling secure and compliant collaboration by ensuring users understand and apply Microsoft Purview policies and Teams capabilities in their daily work. Through the development of clear, effective training and documentation, you will help improve user adoption, reduce support burden, and contribute to the overall success of enterprise technology initiatives.

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

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) 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 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 (“what’s changing and why”) Training rollout planning (pilot groups, phased adoption)
• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Senior