Senior System Engineer

Tier 3 Senior Systems EngineerMicrosoft 365, Infrastructure & Project Engineering

Prosper Solutions

Salary: TBA, depending on qualifications and experience

Benefits: Health benefits and 401(k)

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

Employment Type: Full-Time, Onsite ,

with travel to client locations

"NO REMOTE WFH"

Department: Technical Services / Engineering

Local candidates within approximately 30 minutes of our Saugus office are preferred due to the onsite nature of the role and the need for timely office and client support.

Local candidates within approximately 30 minutes of our Saugus office are preferred due to the onsite nature of the role and the need for timely client support.

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.

We value ownership, accountability, clear communication, strong documentation, and doing the right thing for the client.

About the Role

We are seeking a Tier 3 Senior Systems Engineer to handle complex technical escalations, administer Microsoft 365 and hybrid infrastructure, and assist with project engineering, system architecture, and solution design.

This is a hands-on role combining advanced technical support, systems administration, project delivery, and onsite service. You will work across multiple client environments, mentor service desk staff, and help design and implement secure, reliable technology solutions.

Advanced Microsoft 365 administration is essential. Candidates must be able to independently administer, secure, and troubleshoot Microsoft 365 environments beyond routine user setup and licensing.

Strong experience with on-premises and cloud servers, Azure, advanced networking, cybersecurity, business continuity and disaster recovery (BCDR), and compliance-related technical controls is also required.

Key ResponsibilitiesMicrosoft 365 & Azure

• Administer and troubleshoot Exchange Online, Entra ID, Teams, Teams Phone, SharePoint Online, and OneDrive.
• Configure and maintain Conditional Access, MFA, role-based access, privileged access, and hybrid identity.
• Manage endpoints through Intune, including configuration and compliance policies, application deployment, and Windows Autopilot.
• Implement and support Microsoft Defender and Purview capabilities based on client requirements and licensing.
• Resolve complex email delivery, authentication, permissions, synchronization, and collaboration issues.
• Support Microsoft 365 migrations, tenant assessments, security improvements, and service deployments.
• Administer Azure virtual machines, networking, storage, access controls, monitoring, and backups.
• Use PowerShell for administration, troubleshooting, reporting, and automation.

Servers & Network Infrastructure

• Administer Windows Server, Active Directory, Group Policy, DNS, DHCP, file services, and hybrid environments.
• Maintain on-premises and cloud-hosted servers, virtualization platforms, storage, and supporting infrastructure.
• Configure and troubleshoot firewalls, managed switches, wireless networks, VLANs, routing, VPNs, and network segmentation.
• Diagnose complex connectivity and performance issues using logs, packet captures, and monitoring tools.
• Maintain patching, system hardening, capacity planning, and infrastructure lifecycle standards.

Project Engineering & Solution

Design

• Assist with technical discovery, client assessments, requirements gathering, solution design, and system architecture.
• Evaluate solutions for security, reliability, scalability, supportability, and cost.
• Help develop scopes of work, technical recommendations, implementation plans, estimates, and equipment requirements.
• Own assigned project workstreams involving servers, Microsoft 365, Azure, networking, security, and infrastructure upgrades.
• Perform onsite assessments, installations, migrations, cutovers, and post-deployment support.
• Follow change management, testing, rollback, and service handoff procedures.
• Maintain accurate diagrams, configurations, implementation records, and operational documentation.

Cybersecurity, BCDR & Compliance

• Implement security controls across identities, endpoints, servers, cloud services, and networks.
• Investigate security alerts and assist with incident containment, remediation, and recovery.
• Identify and remediate vulnerabilities, configuration weaknesses, and gaps in security coverage.
• Administer backup and disaster recovery platforms such as Datto, Veeam, Slide, or comparable solutions.
• Troubleshoot backup failures and perform documented restore and recovery tests.
• Help align recovery procedures with client recovery time and recovery point objectives.
• Support compliance readiness through technical control implementation, documentation, and evidence gathering.

Tier 3 Support & Client Service

• Own complex escalations involving Microsoft 365, servers, networks, cloud services, and business applications.
• Provide remote and onsite support for service incidents and project needs.
• Perform root cause analysis and implement lasting fixes for recurring issues.
• Coordinate with vendors and internal teams to resolve high-impact problems.
• Maintain accurate tickets, time entries, technical notes, and client updates.
• Use RMM tools for monitoring, maintenance, patching, and automation.
• Mentor Tier 1 and Tier 2 staff and improve troubleshooting procedures and knowledge base articles.
• Participate in the on-call rotation and scheduled after-hours maintenance or project cutovers as needed.

Required Qualifications

• Five or more years of progressive experience in IT services, systems administration, or infrastructure engineering, including complex escalations and production systems.
• Experience supporting multiple client environments, preferably within an MSP.
• Advanced, hands-on Microsoft 365 administration, including Exchange Online, Entra ID, Intune, Conditional Access, and Microsoft 365 security controls.
• Strong experience with Windows Server, Active Directory, Group Policy, DNS, DHCP, and hybrid identity.
• Hands-on experience administering Azure infrastructure and supporting on-premises and cloud environments.
• Advanced networking knowledge across TCP/IP, subnetting, VLANs, routing, firewalls, switching, wireless, and VPNs.
• CCNA-level networking knowledge backed by practical configuration and troubleshooting experience.
• Experience with VMware, Hyper-V, or comparable virtualization platforms.
• Experience administering backups, resolving failures, and validating recovery through restore testing.
• Working knowledge of cybersecurity controls, identity security, endpoint protection, vulnerability remediation, and compliance-related technical requirements.
• Experience implementing migrations, infrastructure upgrades, and technical projects.
• Proficiency with PowerShell for administration and automation.
• Experience with PSA/ticketing, RMM, and technical documentation platforms.
• Strong communication, documentation, prioritization, and follow-through.
• Ability to work onsite in Saugus and travel to client locations as required.

Candidates should be able to work independently in the core areas of this role, recognize risks, and know when to involve other specialists. Experience with every listed vendor is not required.

Preferred Qualifications

• Current Cisco CCNA certification or higher.
• Relevant Microsoft certifications in Microsoft 365, Azure, identity, endpoint management, or security.
• MSP experience in a Tier 3, senior systems engineer, or project engineering role.
• Experience with Cisco Meraki or other business-grade networking platforms.
• Experience with Microsoft Defender for Business or Endpoint, Defender for Office 365, and Microsoft Purview.
• Familiarity with NIST CSF, NIST SP 800-171, CIS Controls, or CMMC and related technical control implementation.
• Experience with tenant migrations, hybrid identity projects, Azure deployments, and infrastructure modernization.
• Experience developing technical scopes, network diagrams, solution recommendations, and implementation estimates.
• Familiarity with HaloPSA, ConnectWise, Autotask, NinjaOne, Datto RMM, or comparable platforms.

Ideal Candidate

You enjoy solving difficult problems and building better environments. You can move from an advanced service escalation to a project planning discussion, explain technical tradeoffs clearly, and follow through on implementation.

You are calm under pressure, take ownership, and keep clients informed. You understand that successful engineering includes testing, documentation, clear communication, and a smooth transition to ongoing support.

Why Join Prosper Solutions?

• Join a team that values integrity, accountability, and client trust.
• Work across diverse technologies and client environments.
• Contribute to solution design, system architecture, and project delivery.
• Improve security, reliability, and service quality for organizations that depend on us.
• Develop your expertise in cloud services, infrastructure, cybersecurity, and automation.
• Receive competitive compensation, health benefits, and a 401(k).

How to Apply

• Submit your resume and a brief note describing your Microsoft 365 administration experience, MSP background, and recent infrastructure or cloud projects. Include relevant certifications and an example of a complex issue you resolved or a project you helped design and implement.