Senior MSP Engineer at Red Cup IT, Inc.

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.

Required Qualifications

• 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.

Preferred Qualifications

• 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.

Core Competencies

• 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.