Contract Instructor / Microsoft Applications

Enterprise Applications Trainer | 1099 Contract

Contract Type: Independent Contractor (1099)
Duration: 8-Month Contract
Travel: Extensive Travel Required
Schedule: Approximately 2 weeks of travel per month
Compensation: Competitive daily rate

Job Overview

New Horizons, an Educate 360 brand is seeking a motivated trainer with experience in Microsoft technologies, enterprise business applications, or technical instruction to deliver engaging instructor-led training for end users and operational teams.

This role is ideal for someone who enjoys being in front of a group, explaining technology in a clear and practical way, and helping learners build confidence with new systems. If you are energized by presenting, facilitating hands-on learning, and making complex workflows easy to understand, this is a strong opportunity to bring those skills into a high-visibility training engagement.

Training will focus primarily on Microsoft Applications, while also supporting related Microsoft tools and business workflows as needed. The ideal candidate is comfortable learning new systems quickly, guiding learners through live scenarios, and creating a positive, engaging classroom experience.

This is a fast-paced, short-term contract role requiring a strong communicator, quick learner, and confident facilitator who is comfortable traveling and delivering in-person training in professional client environments.

Instructor-Led Training Delivery

• Deliver in-person training on Microsoft Applications and related workflows
• Lead demonstrations and guide learners through practical scenarios
• Support learner understanding and confidence with new systems

Technical Facilitation

• Guide learners through application features and functionality
• Answer questions and provide real-time support during sessions
• Translate system processes into clear, everyday us

Collaboration & Preparation

• Partner with project leads and stakeholders to on training goals
• Participate in Train-the-Trainer sessions to learn systems and delivery expectations
• Prepare materials and adapt content for different audiences
• Provide feedback to improve training delivery and materials

Required Qualifications

Technical Skills

• Familiarity with Microsoft 365 tools, including Teams, Excel, Outlook, SharePoint, and Dynamic Field Service
• Ability to learn new enterprise applications quickly
• Confidence teaching software in a live environment 

Training & Communication

• Experience delivering training, workshops, or group instruction
• Comfortable presenting to diverse audiences
• Strong communication skills with the ability to simplify concepts

Professional Skills

• Fast learner with a strong interest in new technologies
• Engaging facilitator who can connect with learners
• Able to manage live sessions and keep participants on track
• Comfortable troubleshooting basic technical issues
• Willingness to travel to support training delivery

Travel Requirements

• Heavy travel required
• Approximately two weeks of travel per month
• Travel may include client sites in multiple locations

Education & Experience

• Experience in training, software instruction, or business application training preferred
• Background in training, education, consulting, or field operations is valued
• Experience learning and delivering new systems in dynamic environments is a plus

Ideal Candidate Background

Experience in one or more of the following areas is valuable.

• Software or technology instruction
• Teaching with strong technical adaptability
• Corporate or technical training
• Learning and development delivery
• On-site or field-based training
• User enablement and instruction 

Additional Role Context

This role supports a large-scale, nationwide training initiative. Instructors will travel to client locations and deliver structured, in-person training as part of a coordinated rollout. You will participate in onboarding and preparation sessions, work alongside internal client teams, and contribute to a consistent, high-quality learning experience across multiple locations