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OSA Outsourcing Advantage

L2 Systems Engineer – MSP Experience Required

OSA Outsourcing Advantage

. Provide advanced Level 2 technical support for multiple client environments.

Posted 10/23/2026full-timeRemote • Dominican Republic, Philippines, Mexico, Costa Rica, Colombia, AlbaniaMid-LevelSeniorWebsite

Core Competencies

Role fit
Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in providing advanced Level 2 technical support for Microsoft cloud technologies, including Azure and Microsoft 365. Proficient in troubleshooting complex issues across diverse IT environments while maintaining strong communication and organizational skills.

Highest-signal resume keywords
Microsoft 365 SupportAzure Infrastructure ManagementWindows Server AdministrationActive Directory ManagementTroubleshooting Complex Technical Issues

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills
PowerShell ScriptingAzure Virtual MachinesAzure Virtual Desktop (AVD)Group Policy ManagementDirectory SynchronizationNetwork Infrastructure ConfigurationBackup TechnologiesVirtualization PlatformsFirewall ManagementVPN Technologies
Soft Skills
Strong Communication SkillsHighly OrganizedDetail-OrientedProcess-DrivenAbility to Work Independently
Tools & Technologies
Microsoft Entra ID (Azure AD)Exchange OnlineSharePointIntuneDPI-SSLContent FilteringService-Level Agreements (SLAs)Technical Documentation ToolsKnowledge Base ManagementTicketing Systems
Industry Keywords
Managed Services Provider (MSP)Technical SupportClient EnvironmentsIT EnvironmentsTroubleshootingAnalytical SkillsEscalated IssuesTechnical ResolutionsService Call DocumentationBest Practices Implementation

Tech Stack

Tools & technologies
AzureCloudFirewalls

About the role

Key responsibilities & impact
  • Provide advanced Level 2 technical support for multiple client environments.
  • Troubleshoot and resolve complex issues involving Microsoft 365, Azure, networking, servers, endpoints, and infrastructure.
  • Manage and support Microsoft cloud technologies, including Entra ID (Azure AD), Exchange Online, SharePoint, and Intune.
  • Administer and troubleshoot Windows Server environments, including Active Directory, Domain Controllers, Group Policy, and directory synchronization.
  • Configure, maintain, and troubleshoot network infrastructure, including firewalls, VPNs, content filtering, and security solutions.
  • Support virtualization environments, including hypervisors and virtual machines.
  • Assist with Azure infrastructure, including Azure Virtual Machines and Azure Virtual Desktop (AVD).
  • Manage backup solutions, perform troubleshooting, and ensure successful recovery processes.
  • Document service call notes, technical resolutions, system configurations, diagrams, and internal procedures.
  • Create and maintain technical documentation, checklists, and knowledge base articles.
  • Research and implement new technologies, tools, and best practices to improve client environments.
  • Communicate with clients, team members, vendors, and external stakeholders.
  • Prioritize and manage multiple tickets while meeting service-level agreements (SLAs).
  • Collaborate with other engineers and internal teams to resolve escalated issues.

Requirements

What you’ll need
  • Minimum 3 years of experience working in an MSP (Managed Services Provider) environment.
  • Proven experience supporting multiple clients and managing diverse IT environments.
  • Strong troubleshooting and analytical skills with the ability to resolve complex technical issues.
  • Ability to work independently, prioritize tasks, and perform effectively under pressure.
  • Strong communication skills, both written and verbal.
  • Highly organized, detail-oriented, and process-driven.
  • Experience documenting technical processes, configurations, and troubleshooting steps.
  • Microsoft 365 in general, and specifically Entra ID (Azure AD), Exchange Online, SharePoint, and Intune.
  • Experience with PowerShell scripting and automation.
  • Experience with Azure Virtual Machines.
  • Experience with Azure Virtual Desktop (AVD).
  • Windows Server administration.
  • Active Directory and Group Policy.
  • Directory synchronization tools.
  • Hardware firewalls.
  • VPN technologies.
  • DPI-SSL and content filtering.
  • Virtualization platforms.
  • Backup technologies.
  • Prior experience in a Managed Services Provider (MSP) environment is required.

Benefits

Comp & perks
  • Opportunity to work on diverse and exciting projects.
  • Supportive and collaborative work environment.
  • Weekly payments.
  • Weekends off.