Senior MSP Systems Engineer

🕒 January 31

🏄 California – Remote

🏄 California – Remote

⏰ Full Time

🟠 Senior

⚙️ Systems Engineer

👻 Ghost score 76%

What it means: the chance that no one is really hiring for this job.How to read it: 60% or higher means we think this is a ghost. Lower scores are less of a worry.How we score it: age, reposts, open roles vs team size, how fast jobs close, and whether pay is listed.Fine print: an estimate from public data, not a judgment of the company. Real jobs can score high, so treat it as a hint, not a fact.

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Red Cup IT

WebsiteLinkedInAll Job Openings

11 - 50 employees

Founded 2009

💼 Consulting

📦 Logistics

🔒 Cybersecurity

Consulting • Logistics • Cybersecurity

Red Cup IT is a Managed Service Provider (MSP) specializing in cybersecurity, compliance, and virtual CIO services for mid-sized companies and enterprises. The company is dedicated to providing advanced cybersecurity solutions, IT operations support, and managing complex projects while ensuring a cooperative relationship with clients' in-house IT teams. With a comprehensive focus on security, Red Cup IT offers services including IT skill augmentation, project delivery, and cloud management, all tailored to deliver effective and secure IT environments for its clients.

📋 Description

• 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).

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