MSP Senior Systems Engineer at Red Cup IT, Inc.

We are looking for an MSP Senior Systems Engineer is responsible for designing, implementing, and supporting client infrastructure across on‑premises and cloud environments for multiple managed services customers. They serve as a tier‑3 escalation point, lead projects such as cloud migrations and network refreshes, and ensure client environments are secure, stable, and well‑documented.

Key Responsibilities

• Design, deploy, and support servers, storage, and virtualization platforms (VMware/Hyper‑V) for multiple clients in an MSP setting.
• Implement and support Microsoft technologies including Windows Server, Active Directory, Group Policy, Microsoft 365/Office 365, and Exchange (on‑prem and cloud).
• Plan and execute migrations (e.g., Microsoft 365, Azure, on‑prem to cloud, server upgrades, domain consolidations) with minimal downtime.
• Manage and troubleshoot client networks including WAN/LAN, VPNs, switching, wireless, and firewalls (e.g., Cisco, Meraki, Palo Alto, SonicWall).
• Act as a tier‑3 escalation point for complex systems, network, and cloud issues, resolving incidents that exceed service desk capabilities.
• Monitor and maintain client environments using RMM and other MSP toolsets, ensuring patching, backups, and security baselines are in place.
• Implement and maintain security controls such as MFA, conditional access, endpoint protection, and email security (e.g., Mimecast, Proofpoint).​
• Document client environments, architectures, standards, and procedures; maintain accurate records in PSA and knowledge base systems (e.g., ConnectWise).
• Lead or contribute to infrastructure and cloud projects, including network refreshes, server replacements, and modernization initiatives.
• Provide high‑quality client communication, act as a trusted technical advisor, and help manage expectations around scope, timelines, and risk.
• Mentor junior engineers/technicians and contribute to improving internal processes, standards, and automation.

Required Qualifications

• 5+ years of experience designing, implementing, and supporting Windows‑based infrastructure in multi‑site or multi‑tenant environments.
• Prior experience working for a Managed Service Provider (MSP) or similar multi‑client service environment. MSP experience is often explicitly required.
• Strong expertise with:
  - Windows Server, Active Directory, Group Policy, DNS, DHCP, file/print services.
  - Virtualization platforms such as VMware and/or Hyper‑V.
  - Microsoft 365 (Exchange Online, SharePoint, Teams) and related migration projects.
• Solid networking knowledge: TCP/IP, VLANs, VPNs, routing/switching concepts, and firewall configuration/troubleshooting.
• Hands‑on experience with Azure and/or AWS for IaaS/PaaS workloads, including connectivity and identity integration.
• Proven experience troubleshooting complex performance, connectivity, and authentication issues across systems and networks.
• Strong documentation skills and familiarity with PSA/RMM tools commonly used by MSPs (e.g., ConnectWise, similar platforms).

Preferred Qualifications

• Relevant certifications such as Microsoft (Azure/Windows Server/M365), VMware, Cisco, or similar.
• Experience with SAN/NAS storage, converged/hyper‑converged infrastructure, and backup/DR solutions.
• Scripting/automation skills (e.g., PowerShell) to streamline recurring tasks and standardize deployments.
• Experience with zero‑trust/security‑focused designs, including conditional access, identity protection, and advanced email/security tools.