Seasonal Software Trainer (New Hampshire-Based)

About Us

At MSB, supporting educational institutions isn’t just what we do — it’s why we exist. As a Texas-based organization, we partner with school districts to simplify Medicaid management and compliance through expert guidance and innovative technology.

For more than 20 years, we’ve helped educators and administrators navigate complex Medicaid documentation requirements, strengthen reimbursement processes, and remain audit-ready with confidence. By combining hands-on consulting with our proprietary X Logs software, we equip districts with the tools and expertise they need to operate efficiently and compliantly.

Our mission is to empower schools through innovative Medicaid solutions that drive operational excellence and sustainable compliance. We take a collaborative approach, blending advanced technology with deep expertise in Medicaid and Special Education.

Guided by our core values of integrity, efficiency, and service excellence, we work alongside our partners to simplify Medicaid management — allowing schools to maximize resources and focus on what matters most: supporting students and strengthening their communities.

Overview

We are seeking dedicated, professional, and reliable Seasonal Software Trainers to conduct virtual and in-person training sessions across Texas and New Hampshire.

Seasonal Software Trainers play an important role in preparing school districts to successfully use our software and workflows at the start of the school year. Trainers are responsible for delivering engaging training sessions, supporting workshop logistics, troubleshooting basic questions, and ensuring a positive client experience.

As a Seasonal Software Trainer, you will follow internal processes, training materials, and delivery guidelines to ensure consistent, accurate, and high-quality training sessions.

Other Common Job Titles: Software Trainer

Work Location: Remote

Work Hours/Status: $30-$40 per hour, based on experience and qualifications

Travel Requirements: 80%-100% Travel; 5,000+ miles possible, but not guaranteed; Including some travel opportunities to or from a location on a Sunday night or Saturday morning. Travel up to 5,000+ miles is possible, but exact mileage is not guaranteed.

Season date range: July - August; With the possibility of an extension through September

HR/Employee Benefits:

• $30-40/hour for scheduled training sessions
• $13/hour for non-training hours (including preparation, meetings, and administrative tasks)
• Mileage reimbursement for work-related travel
• Hotel accommodations covered for overnight stays, if required
• Meal expenses covered while traveling
• Flexible scheduling available
• Potential opportunity for a full-time position after the season concludes

Your Impact & Duties:

• Be certified in our training methods and consultation by the end of the training period (one week of training at 40 hours/week, or two weeks if training at 20 hours/week)
• Understand our proprietary tool (X Logs) at an administrative level
• Learn presentation and facilitate entire training/workshop
• Directly interact with MSB training staff and the Technology Product Manager
• Provides insight to the Technology Product Manager on high-level situations from other team members.
• Defusing high-stress situations by listening to users and providing speedy, effective resolutions
• Acting as the voice of the company on the front lines and providing excellent customer service
• Maintain a healthy and respectful work environment
• Meet expectations and goals determined by the Technology Product Manager
• Ensure processes are maintained and followed as set by the Technology Product Manager
• Clear communication with Technology Product Manager, other Seasonal Software Trainers, and Program Specialists.

Preferred Qualifications

• Experience working in education, healthcare, software, SaaS, Medicaid, or school district environments.
• Previous experience delivering software training or onboarding.
• Familiarity with X Logs or similar software platforms.
• Experience managing travel schedules, workshop logistics, or customer-facing events.

What We’re Looking For

• Previous experience facilitating training sessions, workshops, presentations, or professional development activities.
• Strong written and verbal communication skills.
• Strong presentation skills and comfort speaking in front of groups.
• Strong organization and time management skills.
• Ability to work independently while also collaborating with internal teams.
• Ability to adapt quickly, troubleshoot issues, and remain calm under pressure.
• Familiarity with Zoom, Google Meet, Google Workspace, Microsoft Office, and other virtual meeting tools.
• Reliable transportation for local travel and willingness to travel frequently. Candidates located in either Texas or New Hampshire are encouraged to apply, as trainers may support virtual sessions across both states.
• Access to a personal laptop that is compatible with Zoom, Google Meet, presentations, and workshop materials is preferred. If needed, MSB may provide a laptop for the season.
• Ability to lift and transport workshop materials, laptops, or small equipment as needed.

Interested in joining our team? We are interested in learning more about you. Apply now!

MSB School Services is an Equal Opportunity Employer committed to providing a diverse environment. We consider applicants for all positions without regard to race, color, religion, creed, gender, national origin, age, disability, marital or veteran status, or any other legally protected status. If you require reasonable accommodation during the application process, please contact us at careers@msbconnect.com.