System Engineer

Location: Greater Boston / Saugus, MA area

Local candidates only due to the onsite nature of the role

and the need for timely client and office support.

Employment Type: Full-Time

Department: Technical Services / Command Center / Service Desk

Prosper Solutions is a veteran-owned Managed Service Provider and Business Service Provider serving organizations that need secure, reliable, and business-aligned technology leadership.

We support clients across industries including nonprofit, commercial organizations, municipalities, professional services, and other mission-driven businesses. Our work goes beyond basic IT support. We help clients improve cybersecurity, modernize infrastructure, manage cloud environments, strengthen compliance readiness, improve operations, and build long-term technology roadmaps.

Our team believes in ownership, accountability, strong documentation, clear communication, and doing the right thing for the client. We are looking for a technical professional who wants to grow, solve real problems, support users, work on projects, and become part of a team that takes pride in delivering excellent service.

The System Engineer "Command Center / Service Desk Engineer" is a hybrid technical role combining frontline support, remote engineering, project assistance, infrastructure support, monitoring, documentation, and escalation work.

This person will support client environments through our ticketing system, remote management tools, security platforms, cloud systems, network tools, and onsite/client-facing engagements when needed. The role requires someone who can troubleshoot user issues, support infrastructure, assist with projects, follow SOPs, create documentation, and participate in ongoing operational improvements.

This is a great role for someone who enjoys a mix of help desk, systems administration, networking, cloud, security tools, automation, and project work.

Provide remote and frontline technical support for client users, workstations, servers, cloud services, networks, and business applications. Troubleshoot hardware, software, Microsoft 365, Windows, macOS, networking, VPN, printing, email, security, and general user issues.

Work tickets through a PSA platform. Use RMM platform for endpoint management, monitoring, patching, scripting, and remote support. Assist with proactive and reactive alerts, including endpoint, server, network, backup, and security-related issues.

Support Microsoft 365 environments, including Exchange Online, Teams, SharePoint, One Drive, Entra , user administration, licensing, and security settings.

Assist with Windows desktop, Windows Server, Azure, identity management, conditional access, MFA, and cloud infrastructure tasks.

Support networking environments, including firewalls, switches, wireless, VPN, VLANs, DNS, DHCP, and general network troubleshooting. Assist with cybersecurity tool management, including endpoint protection, email security, MFA, security awareness tools, logging, and vendor-supported security services.

Participate in backup, disaster recovery, and business continuity support using platforms such as Datto, Veeam, Slide, or similar technologies.

Assist with onsite technical work, client visits, project deployments, hardware installations, migrations, and infrastructure upgrades. Support project engineers and senior technical staff with implementation work, documentation, testing, and client communication.

Create and maintain technical documentation, SOPs, client environment notes, diagrams, checklists, and internal knowledge base articles. Act as a subject matter resource for assigned tools, platforms, or client systems. Assist with dispatch coordination, ticket updates, scheduling support, client follow-up, and basic office administration tasks when needed.

Participate in the on-call rotation after proper onboarding and training. Provide On-Site Tech support to clients when needed. Contribute to continuous improvement, automation, AI-assisted workflows, process cleanup, and operational maturity.

Experience in an MSP, IT service provider, internal IT department, or multi-client technical support environment. Strong troubleshooting ability across Windows desktops, Microsoft 365, basic networking, user support, and common business applications. Experience working with a PSA or ticketing system such as HaloPSA, Connect Wise, Autotask, Service Now, Zendesk, or similar.

Experience with an RMM platform such as Ninja One, Datto RMM, Connect Wise Automate, Kaseya, N-able, or similar. Ability to follow technical processes, document work clearly, update tickets properly, and communicate professionally with clients. Comfortable supporting users remotely, over the phone, through chat/email, and in person when required.

Understanding of endpoint management, patching, remote access, antivirus/EDR tools, backups, and basic security best practices. Strong sense of ownership, urgency,…