IT Technical Training Lead (Senior)

DecisionPoint | Cortek•Chicago, IL

3d•Remote

About The Position

DecisionPoint seeks a Senior IT Technical Training Lead to direct technical workforce assessment, training planning, curriculum alignment, and proficiency improvement for the USMEPCOM ENLIST program. The role leads development and maintenance of the Skills & Proficiency Matrix, role-based learning paths, training schedules, and measurable workforce-development objectives. Training must align with enterprise modernization, system releases, migrations, operational priorities, and future-state technology requirements. The lead coordinates with Government stakeholders, technical leaders, subject matter experts, external training providers, and program leadership so USMEPCOM IT personnel can operate and support enterprise systems alongside contractor personnel. Training may be delivered virtually, in classrooms, side by side, through pair programming, or in other practical formats suited to the technical subject and learners. The position is remote, with preference for candidates located in or near Chicago. Applicants acknowledge that their resume may be included in an active competitive government contract bid.

Requirements

Active Secret clearance or higher.
Bachelor’s degree in Information Technology, Information Systems, Instructional Design, Adult Education, or a related field.
Minimum of 8 years of relevant professional experience.
Current ITIL certification.

Nice To Haves

Current Microsoft Certified Trainer certification.
Experience leading enterprise technical training, workforce development, instructional design, or technical enablement programs.
Experience supporting Department of Defense, federal civilian, or other Government IT programs.
Experience conducting technical workforce assessments and developing competency or proficiency models.
Experience developing and maintaining skills matrices, role profiles, learning paths, curricula, and integrated training schedules.
Experience aligning training with technology releases, migrations, modernization initiatives, and operational priorities.
Experience translating complex technical changes into practical learning objectives and measurable proficiency outcomes.
Experience designing and delivering technical training for infrastructure, cloud, networking, cybersecurity, software development, data, ITSM, or enterprise platforms.
Experience delivering virtual, classroom, side-by-side, pair-programming, lab-based, and blended learning.
Experience coordinating technical subject matter experts, coaches, mentors, external instructors, vendors, and industry training providers.
Experience coordinating Fast Lane or comparable technical training subscriptions and vendor-learning platforms.
Experience developing instructor guides, learner materials, technical labs, exercises, assessments, job aids, and reference materials.
Experience evaluating training effectiveness using completion, assessment, proficiency, performance, and operational-impact measures.
Experience maintaining training records, certification data, schedules, dashboards, and workforce-readiness reports.
Familiarity with adult-learning principles, instructional-systems design, ADDIE, SAM, Bloom’s Taxonomy, or comparable learning methodologies.
Familiarity with ITIL Version 5 or ITIL 4 practices and enterprise IT service-management environments.
Microsoft, AWS, Google Cloud, Cisco, CompTIA, VMware, ServiceNow, cybersecurity, or other relevant technical certifications.
Certified Professional in Talent Development, Certified Professional in Training Management, CompTIA CTT+, or comparable learning-and-development certification.
Experience with learning-management systems, Microsoft Teams, SharePoint, Power BI, virtual lab platforms, or comparable training and reporting tools.
Strong leadership, facilitation, instructional, coaching, and presentation abilities.
Excellent written, verbal, interpersonal, and executive-level communication skills.
Strong curriculum-planning, technical-documentation, and program-coordination capabilities.
Ability to communicate complex technical concepts clearly to audiences with different roles and proficiency levels.
Ability to manage multiple curricula, schedules, stakeholders, vendors, instructors, and delivery priorities.
Ability to work independently while maintaining sound judgment, discretion, accountability, and consistent follow-through.

Responsibilities

Lead technical workforce assessments to identify current capabilities, proficiency levels, role requirements, and emerging skill gaps.
Develop and maintain a comprehensive Skills & Proficiency Matrix for Government IT roles and technical domains.
Establish role-based competency models, proficiency definitions, learning objectives, and measurable qualification criteria.
Design and maintain learning paths aligned with workforce roles, technologies, mission priorities, and modernization roadmaps.
Develop integrated training schedules that account for system releases, upgrades, migrations, operational requirements, and workforce availability.
Translate enterprise IT changes into practical learning objectives, training plans, exercises, and measurable proficiency outcomes.
Coordinate training priorities, schedules, delivery methods, facilities, access, and participation with Government stakeholders.
Align technical training with current and future USMEPCOM enterprise systems, platforms, tools, services, and operational responsibilities.
Develop, tailor, review, and update technical course content for program-specific requirements.
Deliver selected technical courses, workshops, demonstrations, labs, coaching sessions, and knowledge-transfer activities.
Coordinate subject matter expert coaching, mentoring, side-by-side instruction, pair programming, and hands-on technical learning.
Identify and coordinate industry training, certification preparation, vendor courses, and external instructors.
Coordinate Fast Lane activation, enrollment, access, scheduling, utilization, and completion tracking.
Evaluate training providers and recommend solutions based on technical relevance, quality, cost, schedule, and mission value.
Ensure training opportunities support current and future operations across the USMEPCOM enterprise portfolio.
Ensure training content and delivery approaches comply with applicable Department of Defense standards and program requirements.
Develop course outlines, instructor guides, learner materials, exercises, labs, assessments, job aids, reference materials, and evaluation instruments.
Coordinate virtual, classroom, side-by-side, pair-programming, and blended-learning delivery.
Establish methods to measure participation, completion, knowledge acquisition, skill application, proficiency improvement, and operational impact.
Analyze assessment results, learner feedback, completion data, and performance trends to identify improvement opportunities.
Maintain training records, schedules, attendance, completion status, certification information, proficiency results, and supporting evidence.
Develop training dashboards, status reports, gap analyses, and executive briefings for program leadership and Government stakeholders.
Provide training information for Monthly Status Reports, Program Management Reviews, transition planning, and workforce-readiness discussions.
Coordinate training with technical teams responsible for infrastructure, cloud, networking, cybersecurity, software, data, ITSM, and enterprise services.
Support transition-in and transition-out through structured knowledge transfer and workforce-readiness planning.
Maintain a technical training catalog, annual training plan, prioritized backlog, and training-demand forecast.
Capture lessons learned and continually improve curricula, delivery methods, assessments, and learning paths.
Protect sensitive Government, program, personnel, training, and technical information.