Microsoft Technical Trainer Jobs (NOW HIRING)

We are seeking an experienced Technical Trainer to lead technology training and adoption initiatives across a modern enterprise environment. This individual will be responsible for developing and delivering engaging training programs focused on digital workplace technologies, AI-powered tools, collaboration platforms, and productivity solutions.

The ideal candidate combines strong technical knowledge with exceptional communication and facilitation skills, enabling them to translate complex technologies into practical learning experiences that drive user adoption and business value.

This role partners closely with IT, Digital Workplace, Learning & Development, and business stakeholders to identify training needs, develop strategic learning plans, and support enterprise technology initiatives.

• Design, develop, and deliver instructor-led, virtual, and self-paced training programs.
• Create engaging learning content for enterprise technologies, including AI tools, Microsoft 365 applications, collaboration platforms, endpoint technologies, and digital workplace solutions.
• Develop training materials, user guides, job aids, knowledge base articles, and supporting documentation.
• Facilitate onboarding and technology training for new employees.
• Ensure training content remains accurate, current, and aligned with organizational policies and technology standards.

• Partner with technology teams and business stakeholders to support new technology rollouts and adoption initiatives.
• Identify knowledge gaps and recommend targeted learning solutions to improve user proficiency.
• Promote best practices that increase productivity, collaboration, and effective technology utilization.
• Act as a subject matter expert (SME) for end-user technologies and digital workplace solutions.
• Support organizational change initiatives by helping employees successfully adopt new tools and processes.

• Evaluate training effectiveness through learner feedback, assessments, technology adoption metrics, and engagement data.
• Analyze training outcomes and user behavior trends to identify improvement opportunities.
• Continuously enhance learning strategies based on evolving technologies, industry trends, and business priorities.
• Maintain organized and accessible repositories of training resources and documentation.
• Collaborate with leadership to help prioritize training initiatives and align learning objectives with business goals.

• Partner with Digital Workplace, IT, Learning & Development, and business teams to assess training needs and deliver tailored solutions.
• Engage with leaders throughout the organization to understand business challenges and enable technology adoption.
• Support communications related to technology changes, enhancements, and training initiatives.
• Provide mentorship and guidance to peers, trainers, and team members when appropriate.

• Experience developing and delivering technical training programs for enterprise technologies.
• Strong knowledge of Microsoft 365 applications and collaboration platforms.
• Experience supporting digital workplace technologies and end-user productivity tools.
• Familiarity with AI and emerging technologies, including generative AI and productivity-focused AI solutions.
• Ability to create professional training materials, documentation, and knowledge articles.
• Strong presentation, facilitation, and communication skills.
• Experience identifying training needs and implementing solutions that improve adoption and user proficiency.
• Ability to simplify complex technical concepts for both technical and non-technical audiences.
• Proven experience working cross-functionally with technology teams and business stakeholders.

• Experience supporting enterprise technology rollouts, change management, or adoption initiatives.
• Familiarity with platforms such as Microsoft 365, Google Workspace, collaboration tools, and AI-enabled workplace technologies.
• Knowledge of adult learning principles and instructional design best practices.
• Experience measuring training effectiveness through adoption metrics, assessments, and user feedback.
• Strong technical writing and content development skills.
• Experience serving as a subject matter expert, mentor, or training lead.

Job Type & Location

This is a Contract to Hire position based out of Menasha, WI.

The pay range for this position is $30.00 - $50.00/hr.

Individual compensation offered for this position within this range will depend on many factors, including qualifications, skills, relevant experience, job knowledge, geographic location, internal equity, and other pertinent job-related factors.

Eligibility requirements apply to some benefits and may depend on your job classification and length of employment. Benefits are subject to change and may be subject to specific elections, plan, or program terms. If eligible, the benefits available for this temporary role may include the following: • Medical, dental & vision • Critical Illness, Accident, and Hospital • 401(k) Retirement Plan – Pre-tax and Roth post-tax contributions available • Life Insurance (Voluntary Life & AD&D for the employee and dependents) • Short and long-term disability • Health Spending Account (HSA) • Transportation benefits • Employee Assistance Program • Time Off/Leave (PTO, Vacation or Sick Leave)

This is a hybrid position in Menasha,WI.

This position is anticipated to close on Sep 11, 2026.

We're partners in transformation. We help clients activate ideas and solutions to take advantage of a new world of opportunity. We are a team of 80,000 strong, working with over 6,000 clients, including 80% of the Fortune 500, across North America, Europe and Asia. As an industry leader in Full-Stack Technology Services, Talent Services, and real-world application, we work with progressive leaders to drive change. That's the power of true partnership. TEKsystems is an Allegis Group company.

The company is an equal opportunity employer and will consider all applications without regards to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.

We’re a leading provider of business and technology services. We accelerate business transformation for our customers. Our expertise in strategy, design, execution and operations unlocks business value through a range of solutions. We’re a team of 80,000 strong, working with over 6,000 customers, including 80% of the Fortune 500 across North America, Europe and Asia, who partner with us for our scale, full-stack capabilities and speed. We’re strategic thinkers, hands-on collaborators, helping customers capitalize on change and master the momentum of technology. We’re building tomorrow by delivering business outcomes and making positive impacts in our global communities. TEKsystems and TEKsystems Global Services are Allegis Group companies. Learn more at TEKsystems.com.

The company is an equal opportunity employer and will consider all applications without regard to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.

San Francisco Fair Chance Ordinance: Pursuant to the San Francisco Fair Chance Ordinance, for all positions located in the city and county of San Francisco, we will consider for employment qualified applicants with arrest and conviction records.

Massachusetts Lie Detector: It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Use of Artificial Intelligence (AI): We may use Artificial Intelligence (AI) to support parts of our hiring process, including sourcing, screening, and evaluating candidates. AI helps assess applications and qualifications, but final decisions are made by our hiring team. By applying, you acknowledge and agree that your application may be reviewed using AI tools.