Microsoft 365 Trainer I

HEARTLAND-BUSINESS-SYSTEMS-LLC; Little Chute (WI); Hybrid; USD 50,000 - 70,000; Full time

Job summary

HEARTLAND-BUSINESS-SYSTEMS-LLC seeks a Microsoft 365 Trainer I to deliver impactful training experiences in Little Chute, Wisconsin. This role emphasizes maximizing adoption of Microsoft 365 tools through both live instruction and content creation, with a focus on customer success.

The ideal candidate will have strong hands-on experience with Microsoft 365, instructional skills, and the ability to build relationships with learners. Responsibilities include maintaining training materials and facilitating engaging, scenario-based learning sessions.

Qualifications

• Strong hands-on experience using Microsoft 365 productivity tools.
• Experience presenting to technical and non-technical audiences.
• 2+ years of experience delivering live training, facilitation, or professional instruction.

Responsibilities

• Deliver 10–15 live instructor led training sessions per week.
• Facilitate Microsoft 365 end user training courses.
• Maintain training materials to align with product enhancements.

Skills

Presentation & Facilitation Skills

Active Listening

Adaptability

Customer Oriented

Communication

Organization & Time Management

Collaboration

Innovative

Relationship Building

Education

Associate Degree in Business or related IT discipline

Tools

Microsoft 365

Microsoft Teams

SharePoint

OneDrive

Outlook

OneNote

Job description

Position Summary

The Microsoft 365 Trainer I is a member of the Modern Work practice responsible for delivering high impact, scenario-based Microsoft 365 and Copilot training experiences to customers. This role focuses on helping organizations maximize adoption and effective use of Microsoft 365 tools through live instruction, engaging learning content, and ongoing program promotion. The Microsoft 365 Trainer balances primarily virtual, but occasional classroom delivery with content creation, training operations ownership, and marketing collaboration to drive measurable learning outcomes.

Roles and Responsibilities / Essential Functions

• Deliver 10–15 live instructor led training sessions per week, primarily remote and delivered via Microsoft Teams.
• Facilitate Microsoft 365 end user training courses, including but not limited to, Microsoft Teams 101 (Basics), Microsoft Teams 201 (Advanced), Microsoft Teams Phone, Microsoft Copilot Basics, Outlook productivity and best practices, OneNote usage and organization, OneDrive and storage best practices, SharePoint fundamentals, power user, and administrative concepts.
• Deliver Customer Immersion Experience (CIE) training covering cross application navigation and integrated Microsoft 365 workflows.
• Provide role based and scenario driven examples aligned to how customers actually work.
• Regularly update and maintain training materials to align with product enhancements, customer feedback and engagement insights, and evolving best practices across Microsoft 365 and Copilot.
• Own the training scheduling process, including session planning, calendar coordination, and capacity management.
• Ensure consistent, high quality learner experiences across all training engagements.
• Collaborate with presales, consulting, and marketing teams to align training offerings with customer needs.
• Create and publish regular social media content to promote training offerings, upcoming sessions, and learning outcomes.
• Contribute to internal and external blogs or posts related to Microsoft 365 adoption, enablement, and productivity.
• Communicate clearly with internal team members regarding schedules, deliverables, and training priorities.
• Build lasting customer relationships through exceptional facilitation, responsiveness, and professionalism.
• Engage in relevant user groups and community forums to build skillsets and strengthen the Heartland brand.
• Embrace new training topics, delivery formats, and related workstreams as business needs evolve.
• Meet annual billable hour goal, as defined by HBS. This number may change over time as the business evolves.

Requirements

Competencies

• Presentation & Facilitation Skills – Ability to confidently deliver engaging, interactive training sessions.
• Active Listening – Ability to understand learner needs and adjust delivery accordingly.
• Adaptability – Ability to adjust to product changes, audience needs, and delivery formats.
• Customer Oriented – Ability to prioritize customer success and learning outcomes.
• Communication – Ability to convey technical concepts in clear, accessible language.
• Organization & Time Management – Ability to manage high-volume training schedules and content updates.
• Collaboration – Ability to work effectively with internal teams across practices.
• Innovative – Ability to continuously improve learning experiences and training formats.
• Relationship Building – Ability to build trust with learners, customers, and internal teammates.

Required Experience

• Strong hands‑on experience using Microsoft 365 productivity tools (Teams, SharePoint, OneDrive, Outlook, OneNote)
• Experience presenting to technical and non-technical audiences

Preferred Experience

• 2+ years of experience delivering live training, facilitation, or professional instruction
• Experience delivering Microsoft 365 or Copilot training in a consulting or professional services environment
• Experience with role based learning, curriculum development, or instructional design
• Experience supporting Microsoft 365 adoption, change management, or enablement programs
• Experience creating promotional or educational content for social media or digital platforms

Required Skills, Education and/or Certifications

• Associate Degree in Business or related IT discipline, or equivalent work experience

Preferred Skills, Education and/or Certifications

• Bachelor’s Degree in Business or related IT discipline
• Microsoft 365 or Microsoft Certified Trainer (MCT) certification(s)
• Experience with Copilot or AI-enabled productivity tools

Equal Opportunity Employer - Including Disabled and Veterans