Red Cup IT

Senior MSP Systems Engineer

Red Cup IT

full-time

Posted on:

Location Type: Remote

Location: California • United States

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Job Level

Senior

Tech Stack

AWSAzureCloudDNSFirewallsSwitchingTCP/IPVMware

About the role

  • 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.

Requirements

  • 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).
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
Windows ServerActive DirectoryGroup PolicyDNSDHCPVMwareHyper-VMicrosoft 365AzureAWS
Soft Skills
client communicationtechnical advisorymentoringprocess improvementdocumentation