Red Cup IT · 18 hours ago
MSP Senior Systems Engineer
United States
Full-time
Remote
Senior Level
5+ years expRed Cup IT is seeking an MSP Senior Systems Engineer responsible for designing, implementing, and supporting client infrastructure across on-premises and cloud environments. The role involves leading projects, ensuring security and stability of client environments, and serving as a tier-3 escalation point for complex issues.
Cloud ComputingCloud ManagementCloud SecurityCyber SecurityEnterprise Resource Planning (ERP)Information TechnologyIT ManagementSales Automation
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
Qualification
Required
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
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
Company
Red Cup IT
Red Cup IT is an enterprise-grade Cybersecurity & IT firm that provides MSP, MSSP, Project Delivery, and Skill Augmentation solutions.
11-50 employees
Funding
Current Stage
Early StageLeadership Team
Dan Le
Founder and CEO
Company data provided by crunchbase