Level 2 and Level 3 + Senior IT Support Engineers (Remote)

Established in 2016, Support Adventure is an expat outsourcing company that provides people the opportunity to live and work in exciting cities worldwide while offering tech support online in a location independent manner.

Support Adventure offers worldwide remote work opportunities with the freedom to work from anywhere, as long as you have a stable power supply and internet connection. You can choose to stay in Jamaica or relocate to a different one without worrying about finding a new job. This level of flexibility is a significant benefit of working with Support Adventure.

We are currently seeking experienced Level 2 and Level 3 + Senior IT Support Engineers to work remotely on our clients’ helpdesks located around the world. You will work with international MSP clients, offering proactive support, managing escalations, resolving complex technical issues, and playing a key role in infrastructure management and project delivery.

Depending on your level of experience and skill set, you will be working as an Escalation/Level 2 Helpdesk Technician, Infrastructure/Project Engineer, Systems Administrator, or NOC Engineer, all in a 100% remote capacity. You’ll be joining a team of almost 200 technicians of various levels working with some of the latest industry-standard tools and platforms commercially available.

Candidates must have hands-on experience in most or all of the following areas:

• Advanced remote desktop support (Windows 10/11, some macOS a bonus)
• Microsoft 365 administration and deployment (Exchange Online, SharePoint, Teams, Intune)

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• Windows Server administration (2012–2022), Active Directory, GPOs, DNS/DHCP, Entra AD
• Virtualization technologies (Azure, AWS, VMware, Hyper-V), including on-prem to cloud migrations
• Network troubleshooting (VPN, firewalls, switches, routing) and familiarity with cloud-based networking solutions (Cisco Meraki, Azure Virtual Networks)
• RMM and ticketing system experience in a high-paced MSP environment (ConnectWise, Autotask, NinjaOne, etc.)
• Experience with backup and disaster recovery solutions (Datto, Veeam, etc.)
• Scripting or automation skills (PowerShell, Bash, etc.) are a plus

The following skills and abilities are also a must:

• A high level of Business English, proficiency in both written and verbal, is essential.
• A passion for customer service and great ‘soft’ skills.

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• Ability to present technical information in plain terms to non-technical users.
• Strong documentation habits and attention to detail, especially in ticketing systems.
• Eagerness to stay updated with the latest technologies and best practices.

What Support Adventure offers:

We offer a competitive salary, usually in the range of USD$2600-4300+ monthly, depending on position and experience. Payouts are made in USD, EUR, or GBP.

You will be joining a team of seasoned technicians from all over the world, working remotely with users from various English-speaking countries across the globe.

Working with Support Adventure, you'll have a dedicated team of people that will continuously work with you and our clients to get you the best working experience possible and assist you with any aspect of your personal remote working adventure. We also offer a comprehensive wellness program that includes access to a wellness coach, online yoga and Pilates classes, and participation rewards all free to our contractors.