System Engineer

Prosper Solutions; Saugus (MA); On-site; USD 65,000 - 75,000; Full time

Benefits offered by this job

Health benefits

401(k)

Job summary

Prosper Solutions is seeking a Tier 2 Systems Engineer / Service Desk Engineer in the Greater Boston / Saugus, MA area. You will provide day-to-day technical support, handle escalations, and assist with deployments and documentation.

You should have at least two years of relevant IT experience in an MSP environment, and be comfortable working onsite to support clients and teams across Microsoft 365, cloud services, and hybrid networks.

Qualifications

• At least two years of MSP IT support, technical services, or systems administration experience.
• Strong troubleshooting across Windows desktops, Microsoft 365, basic networking, and business apps.
• Experience with PSA/ticketing systems (HaloPSA, ConnectWise, Autotask, ServiceNow, Zendesk).
• Experience with RMM platforms (NinjaOne, Datto RMM, ConnectWise Automate, Kaseya, N-able).
• Hands-on supporting Microsoft 365 (Exchange Online, Teams, SharePoint, OneDrive, Entra ID, Azure).
• Ability to follow procedures, document work clearly, and escalate when needed.

Responsibilities

• Provide remote and onsite technical support for client users, workstations, servers, cloud services, networks, and business apps.
• Troubleshoot Windows, macOS, Microsoft 365, hardware, software, email, VPN, printing, and connectivity issues.
• Manage tickets in PSA, with clear notes and timely updates to clients.
• Resolve Tier 2 issues and escalate advanced problems to engineering resources.
• Use RMM tools for remote support, endpoint management, monitoring, patching, and scripting tasks.
• Monitor backups and assist with recovery tasks using Datto, Veeam, Slide, or similar.

Skills

MSP IT support

Troubleshooting

Documentation

On-call support

Customer support

Ticketing

Tools

HaloPSA

ConnectWise

Autotask

ServiceNow

Zendesk

NinjaOne

Datto RMM

ConnectWise Automate

Kaseya

N-able

Job description

Prosper Solutions

Salary: $65,000–$75,000 annually, depending on qualifications and experience

Benefits: Health benefits and 401(k)

Location: Greater Boston / Saugus, MA area

Department: Technical Services / Command Center / Service Desk

Local candidates within 30 min of driving distance to the office only due to the onsite nature of the role and the need for timely office and client support.

Address: 999 Broadway, Suite #304, Saugus MA 01906

About Prosper Solutions

Prosper Solutions is a veteran-owned Managed Service Provider and Business Service Provider helping organizations build secure, reliable, and business-aligned technology environments.

We support nonprofit organizations, commercial businesses, municipalities, professional services firms, and other mission-driven organizations. Our services include IT support, cybersecurity, cloud management, infrastructure modernization, compliance readiness, and long-term technology planning.

Our team values ownership, accountability, clear communication, strong documentation, and doing the right thing for the client. We are looking for a technical professional who enjoys solving problems, supporting users, contributing to projects, and growing their skills.

About the Role

The Tier 2 Systems Engineer / Service Desk Engineer combines day-to-day technical support with systems administration, monitoring, infrastructure support, project assistance, and documentation.

You will resolve support issues, handle escalations from frontline support, maintain client systems, and assist with technical deployments. You should be comfortable independently troubleshooting common issues, following established procedures, and escalating complex problems with clear documentation.

This is an opportunity for someone with at least two years of relevant IT experience who wants to grow across Microsoft cloud services, networking, cybersecurity, infrastructure, and automation.

Key Responsibilities

• Provide remote and onsite technical support for client users, workstations, servers, cloud services, networks, and business applications.


• Troubleshoot Windows, macOS, Microsoft 365, hardware, software, email, VPN, printing, connectivity, and general user issues.


• Manage assigned tickets through our PSA platform, maintaining accurate notes, timely updates, and clear client communication.


• Resolve Tier 2 support issues and elevate advanced or high-impact problems to the appropriate engineering resources.


• Use RMM tools for remote support, endpoint management, monitoring, patching, and approved scripting tasks.


• Investigate endpoint, server, network, backup, and security alerts, following documented response and escalation procedures.


• Support Microsoft 365 environments, including Exchange Online, Teams, Teams Phone, SharePoint, OneDrive, Entra ID, user accounts, licensing, and access permissions.


• Assist with Windows Server, Active Directory, Group Policy, DNS, DHCP, file servers, Azure, and hybrid cloud environments.


• Troubleshoot networking issues involving firewalls, switches, wireless networks, VPNs, and VLANs.


• Assist with endpoint protection, email security, MFA, identity and access management, and other security tools.


• Monitor backups and assist with recovery tasks using platforms such as Datto, Veeam, Slide, or similar technologies.


• Participate in client visits, hardware installations, migrations, onboarding, infrastructure upgrades, and project deployments.


• Support project engineers with implementation tasks, testing, documentation, and client communication.


• Create and maintain technical documentation, SOPs, client environment notes, checklists, diagrams, and knowledge base articles.


• Assist with ticket coordination, scheduling, client follow-up, and related operational tasks when needed.


• Participate in the on-call rotation after appropriate onboarding and training.


• Contribute ideas for process improvements, automation, and responsible use of AI-assisted workflows.

Required Qualifications

• At least two years of relevant "MSP" IT support, technical services, or systems administration 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 with a PSA or ticketing system such as HaloPSA, ConnectWise, Autotask, ServiceNow, Zendesk, or similar.


• Experience with an RMM platform such as NinjaOne, Datto RMM, ConnectWise Automate, Kaseya, N-able, or similar.


• Hands-on experience supporting Microsoft 365 users and services, with familiarity across Teams, Teams Phone, SharePoint, OneDrive, Exchange Online, Entra ID, and Azure.


• Working knowledge of Windows Server, Active Directory, Group Policy, DNS, DHCP, file servers, and hybrid cloud environments.


• General knowledge of cybersecurity operations, identity and access management, compliance controls, email security, MFA, endpoint protection, and security monitoring.


• Understanding of endpoint management, patching, remote access, backups, and security best practices.


• Ability to follow technical procedures, document work clearly, prioritize assigned tickets, and communicate professionally.


• Comfortable supporting users by phone, remote session, chat, email, and in person.


• Strong ownership, accountability, follow-through, and judgment about when to elevate.


• Ability to work independently while collaborating with other technical team members.


• Willingness to learn new platforms and take on increasing technical responsibility.

Candidates should have a solid foundation and relevant hands-on experience. Expert-level knowledge of every listed platform is not expected.

Preferred Skills

• Previous MSP experience supporting multiple client environments.


• Experience with Microsoft Power Platform, Power Automate, PowerShell, scripting, or automation.


• Familiarity with VMware or other virtualization platforms.


• Experience with Cisco Meraki firewalls, switches, wireless networks, VPNs, or other cloud-managed networking platforms.


• Familiarity with Datto, Slide, Veeam, or similar backup and disaster recovery solutions.


• Experience supporting macOS and mobile device management platforms.


• Experience assisting with migrations, client onboarding, infrastructure upgrades, and technical deployments.


• Relevant Microsoft, CompTIA, Cisco, or other technical certifications in cloud, endpoint administration, networking, identity, or security.
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