We are looking for a Senior MSP Engineer is responsible for designing, implementing, and supporting client IT infrastructure across on‑premises and cloud environments within a managed services model. They act as a senior technical escalation point, lead complex projects and migrations, and help standardize and improve service delivery processes.
Key Responsibilities- Provide Tier 2/3 escalation support for servers, networks, cloud services, and line‑of‑business applications.
- Design, implement, and support Windows Server, Active Directory, virtualization (VMware/Hyper‑V), storage, and backup solutions.
- Plan and execute migrations and deployments (e.g., Microsoft 365/Exchange Online, Azure/AWS workloads, server upgrades, network refreshes).
- Configure and manage networking: firewalls, switches, VLANs, VPNs, Wi‑Fi, and routing for SMB/enterprise clients.
- Administer cloud platforms such as Microsoft 365, Azure AD, Intune, and other SaaS services commonly used in MSP environments.
- Use RMM and PSA tools to monitor systems, remediate alerts, manage tickets, and document all work accurately.
- Perform security hardening and remediation: patching, configuration baselines, identity and access controls, backup/DR validation, and endpoint protection.
- Lead or participate in client onboarding, technical assessments, and standardization initiatives.
- Create and maintain technical documentation, runbooks, and diagrams for client environments.
- Mentor junior engineers and service desk staff, providing guidance on best practices and troubleshooting approaches.
- Participate in on‑call rotations and provide after‑hours support for critical incidents when required.
- Collaborate with account management to provide technical input for roadmaps, proposals, and client strategy.
- 5+ years of experience in an MSP or multi‑client IT services environment in a systems/network engineering role.
- Strong hands‑on experience with Microsoft Windows Server, Active Directory, Group Policy, DNS, DHCP, file/print services.
- Proficiency with virtualization technologies (VMware and/or Hyper‑V).
- Solid networking knowledge: TCP/IP, VLANs, VPNs, firewalls, routing, switching, and Wi‑Fi.
- Experience administering Microsoft 365 (Exchange Online, SharePoint, OneDrive, Teams) and Azure AD/Entra ID.
- Familiarity with RMM and PSA platforms used in MSPs (e.g., ConnectWise, Autotask, N‑able, Datto, etc.).
- Strong troubleshooting skills across servers, networks, and endpoints in heterogeneous environments.
- Excellent documentation, communication, and customer‑facing skills.
- Ability to prioritize and manage multiple tickets and projects in a fast‑paced, SLA‑driven environment.
- Experience designing and executing cloud migrations (Microsoft 365, Azure, or AWS).
- Experience with security tools and concepts (MFA, conditional access, email security, EDR, zero‑trust principles).
- Relevant certifications such as MCSA/MCSE, AZ‑104/305, CCNA/CCNP, VMware, or similar.
- Prior experience in a senior, lead, or mentoring role within an MSP.
- Customer‑centric mindset and strong sense of ownership.
- Analytical and systematic problem solving.
- Clear written and verbal communication with non‑technical stakeholders.
- Team collaboration and willingness to coach others.
Top Skills
What We Do
Red Cup IT is an enterprise-grade IT firm that provides MSP, MSSP, Project Delivery, and Skill Augmentation solutions. We have been in business for twelve years and support clients across the United States. Our hallmark is the delivery of skillsets in more than 100 IT solutions and SaaS applications. Red Cup IT’s technical staff constantly cross-train across their specializations. Our company culture is unusual for firms of our nature. We strongly believe in IT skill transfer and knowledge sharing. Our customers’ business and IT leaders appreciate that we take care of the technical details so that they can focus on their strategic and business missions. Our end users appreciate the white glove support we provide. We focus on vendor relationship development and know how to get the most out of our partnerships on behalf of our clients.








