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Osa

L2/L3 Systems Engineer (MSP Experience Required)

  • Seen live on Osa's site today
  • Mid level
Pay
Not stated
Location
Santiago de los Caballeros, Santiago Province, Dominican Republic
Open for
10+ days
First seen
Oct 25, 2026
Apply on Osa's site (opens in a new tab)

Posting record

No flags

Open 10+ days

The posting's record, oldest first
  1. Osa's site dates the posting
  2. Ghostless first sees this listing
  3. Last checked: still up
How we know

It hasn't been reposted, listed twice, or left up unusually long, and the posting doesn't say it's a talent pool.

Ghostless records the day it first sees a posting, so a repost can't reset its age. This one was already up when Ghostless started tracking Osa, so its true age is longer.

Last checked Nov 4, 2026.

How well do you match?

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What it asks of you

3+ years of experience
“Minimum 3 years of experience working in an MSP (Managed Services Provider) environment .” (quoted from the posting)

What the posting discloses

Not stated: Pay, real vacancy, AI screening.

Why these three

Ontario requires postings from employers with 25 or more staff to state the pay, whether the vacancy exists, and whether AI screens applicants.

Some employers add pay only on their own site. Check the original posting before you rule it out.

Skills mentioned

About the role

Outsourcing Staffing Advantage is seeking an experienced L2/L3 Systems Engineer with a strong background in Managed Services Providers (MSP) environments to join our team. The ideal candidate will have hands-on experience supporting multiple clients, troubleshooting complex infrastructure issues, and managing Microsoft-based environments.

This role requires a highly technical, organized, and proactive professional who can independently diagnose issues, research solutions, and deliver exceptional support across diverse client environments.

Responsibilities

  • Provide advanced Level 2 and Level 3 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 effectively with clients, team members, vendors, and external stakeholders.
  • Prioritize and manage multiple tickets while meeting service-level agreements (SLAs).
  • Work collaboratively with other engineers and internal teams to resolve escalated issues.

Requirements

  • 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
  • Azure Virtual Machines
  • 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

Candidates whose only experience is in-house IT, a single-company help desk, or an unrelated field are not a fit for this role. Prior experience in a Managed Services Provider (MSP) environment is required.

Preferred Qualifications

  • Experience working with multiple MSP tools and platforms.
  • Microsoft certifications such as:
  • Microsoft Certified: Azure Administrator Associate
  • Microsoft 365 Certified: Administrator Expert
  • Microsoft Certified: Endpoint Administrator Associate
  • Experience managing enterprise Microsoft environments.
  • Strong understanding of cybersecurity best practices.
  • Experience with firewall vendors such as SonicWall, Fortinet, Meraki, Palo Alto, or similar technologies.
  • Experience supporting hybrid cloud environments.
  • Experience creating network diagrams and technical documentation.
  • Familiarity with IT service management processes and ticketing systems.
  • Experience working directly with clients in a consulting or managed services capacity.

Benefits

  • Opportunity to work on diverse and exciting projects.
  • Supportive and collaborative work environment.
  • Weekly payments.
  • Weekly incentives based on performance.
  • Weekends off.
  • Hiring bonus.
  • Loyalty Bonus
  • Annual Performance Salary Review Increases up to 10%
  • Paid Breaks
  • Growth opportunities.
  • Referral bonus.
  • National holidays pay double the hourly rate.
  • US holidays off when applicable.
  • Best work environment in Santiago.
  • Morning shift available.

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