MSP Trainer

The MSP Trainer is responsible for designing, delivering, and continuously improving technical, operational, and security training programs within a 24/7 Managed Services Provider (MSP) environment. This role ensures that technicians and client-facing teams are effectively onboarded, consistently follow standardized processes, and remain current on tools, industry trends, security requirements, and account-specific needs.

The ideal candidate combines hands-on MSP experience, strong instructional design and facilitation skills, operational awareness, and the flexibility to remain actively engaged with live support environments when needed.

Key Responsibilities:

Training Strategy & Program Development

• Design, implement, and maintain role-based training programs for Service Desk, NOC, Projects, and Client Success teams.
• Develop structured onboarding curricula covering technical foundations, MSP tools, cybersecurity practices, and service delivery standards.
• Apply adult learning principles (e.g., ADDIE, Bloom’s Taxonomy) to create effective instructor-led, virtual, and self-paced learning experiences.

Technical & Tool Enablement

• Deliver training on PSA and RMM platforms, including ticket lifecycle management, SLAs, escalations, workflows, dashboards, and reporting.
• Conduct Microsoft 365 training sessions, covering administration fundamentals and adoption best practices for Teams, SharePoint, Exchange Online, OneDrive, and Intune (baseline).
• Support cybersecurity awareness initiatives, including phishing prevention, MFA adoption, secure data handling, and secure collaboration best practices.

Instruction & Facilitation

• Facilitate live, virtual, and in-person training sessions, workshops, hands-on labs, and assessments.
• Adapt facilitation style for both technical and non-technical audiences, including engineers, leadership, and SMB end users.
• Reinforce standard operating procedures (SOPs) and service delivery best practices through coaching and follow-up.

Documentation & Knowledge Management

• Create, maintain, and regularly update SOPs, runbooks, knowledge base articles, quick-start guides, and training materials.
• Own the MSP knowledge base to ensure content remains accurate, current, and aligned with active tools, services, and account requirements.
• Proactively update documentation and training materials in response to product changes, new service offerings, account updates, or industry changes.

Learning Management & Reporting

• Administer the Learning Management System (LMS), including course creation, enrollments, completion tracking, and reporting.
• Define and track training effectiveness using KPIs such as onboarding ramp time, FCR, CSAT, MTTR, backlog reduction, and certification completion rates.
• Provide regular training performance reports and insights to leadership and operational stakeholders.

Cross-Functional Coordination & Communication

• Coordinate closely with HR, Recruitment, Workforce Management, Quality Assurance, and Operations to align training delivery with hiring plans, workforce readiness, and operational goals.
• Provide timely and accurate updates on trainee progress, including onboarding completion, milestone achievements, assessment results, and certifications earned.
• Communicate training outcomes that may impact employee compensation, readiness status, role eligibility, or advancement.

Continuous Learning & Operational Immersion

• When no formal training sessions are scheduled, proactively develop and update assessments, skills checks, and training content to remain fully aligned with account requirements.
• Design, distribute, and track bi-monthly (twice-monthly) quizzes for MSP teams to reinforce awareness of: Industry trends and security updates, Company tools, services, and policies, Account-specific workflows and requirements
• In cases of new products, technologies, or service offerings, actively immerse in operations by taking calls or working tickets as needed to fully understand real-world support challenges and account needs.
• Use operational exposure to continuously refine and improve training programs.

Schedule, Travel & Work Location Requirements

• Must be flexible to work any shift, including nights, weekends, and holidays, in support of a 24/7 service delivery model.
• Schedule may vary based on training demands, business needs, and account coverage.
• Must be willing to report on-site to company offices or client locations to conduct in-person trainings, onboarding sessions, and workshops.
• Must be willing and able to travel as needed to support training initiatives at other locations.
• Adaptability and flexibility are essential for success in this role.
  

• 3+ years of experience in an MSP or IT services environment (Service Desk, NOC, Projects, or Client Success).
• Proven experience delivering training using adult learning principles.\
• Hands-on experience with PSA and RMM platforms (e.g., ConnectWise, Kaseya, NinjaOne, Datto, N-able).
• Foundational Microsoft 365 administration experience (Teams, SharePoint, Exchange Online, OneDrive, Intune).
• Experience supporting or delivering cybersecurity awareness training.
• Strong technical documentation and content development skills.
• Excellent verbal and written communication skills.
• Data-driven mindset with experience measuring training effectiveness.
• Experience managing or administering an LMS.

Preferred (Nice-to-Haves)

• Certifications such as Microsoft Certified Trainer (MCT), ITIL Foundation, CompTIA A+/N+/S+, or Microsoft 365 certifications.
• Experience across multiple PSA/RMM platforms.
• PowerShell scripting experience for demos or lab environments.
• Familiarity with Intune compliance policies and baselines.
• Experience with eLearning development tools (Articulate Storyline, Camtasia, Adobe Captivate).
• Experience building client-facing adoption programs or internal train-the-trainer initiatives.