Red Cup IT, Inc.

Provide first- and second-level support to MSP clients, troubleshooting hardware, software, and network issues, and managing client accounts. | 3+ years of IT support experience, MSP experience preferred, strong knowledge of Windows and networking, experience with Microsoft 365, ticketing systems, and RMM tools. | We are looking for an MSP Service Desk & Support who is responsible for providing first- and second-level technical support to MSP clients across multiple environments. This role acts as the primary point of contact for client IT issues, ensuring incidents and service requests are resolved efficiently, professionally, and in accordance with SLAs. The ideal candidate is customer-focused, technically competent, and comfortable supporting multiple clients, systems, and priorities in a fast-paced MSP environment. Client Support & Service Desk Operations Serve as the first point of contact for client support requests via ticketing system, phone, and email Troubleshoot and resolve Tier 1 and Tier 2 technical issues in a timely manner Escalate complex issues to senior engineers or specialized teams when required Document all troubleshooting steps, resolutions, and client communications in the PSA/ticketing system Maintain high levels of customer satisfaction and professionalism Technical Support Support Windows and macOS workstations Troubleshoot hardware, software, and peripheral issues Manage user accounts, permissions, and security groups (Active Directory / Azure AD) Provide Microsoft 365 support (Exchange, Teams, OneDrive, SharePoint) Perform basic network troubleshooting (DNS, DHCP, VPN, Wi-Fi) Support RMM tools, endpoint security, and patching systems Assist with onboarding/offboarding users and device provisioning MSP Processes & Best Practices Follow ITIL-aligned incident, problem, and change management processes Meet or exceed SLA and response time requirements Identify recurring issues and recommend improvements Participate in knowledge base creation and maintenance Follow security best practices and MSP standards Required Skills & Qualifications 3+ years of IT support experience (MSP experience strongly preferred) Strong knowledge of Windows OS and basic networking concepts Experience with Microsoft 365 administration Familiarity with ticketing/PSA systems (e.g., ConnectWise, Autotask, HaloPSA, Zendesk) Experience using RMM tools (e.g., NinjaOne, Datto, N-able, ConnectWise Automate) Understanding of endpoint security tools and MFA concepts Soft Skills Excellent communication and customer service skills Strong troubleshooting and analytical abilities Ability to manage multiple tickets and priorities simultaneously Comfortable working in a fast-paced, client-facing environment Professional demeanor and positive attitude Preferred Qualifications MSP experience supporting multiple clients and environments ITIL Foundation certification CompTIA A+, Network+, or Microsoft certifications Experience with Azure AD, Intune, or basic cloud administration Familiarity with VoIP systems and SaaS applications Performance Metrics SLA compliance and response times Ticket resolution quality and documentation Client satisfaction scores Adherence to MSP processes and security standards

Design, implement, and support client infrastructure, lead cloud migrations, and act as a tier-3 escalation point in an MSP setting. | At least 5 years of experience with Windows infrastructure, MSP environment experience, virtualization, networking, and cloud platforms, with relevant certifications preferred. | We are looking for an MSP Senior Systems Engineer is responsible for designing, implementing, and supporting client infrastructure across on‑premises and cloud environments for multiple managed services customers. They serve as a tier‑3 escalation point, lead projects such as cloud migrations and network refreshes, and ensure client environments are secure, stable, and well‑documented. Key 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. Required Qualifications 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 Qualifications 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.

Maintain and support client IT environments, including server, network, and cloud infrastructure, ensuring high availability and security. | Several years of experience in systems engineering or administration, with strong knowledge of Windows Server, Active Directory, Microsoft 365, virtualization, and networking fundamentals. | We are looking for an MSP Systems Engineer who is responsible for maintaining, supporting, and improving client IT environments across on‑premises and cloud infrastructure, ensuring high availability, security, and performance for multiple customers in a fast‑paced managed services setting. Key Duties and Responsibilities: Monitor, maintain, and administer client servers, workstations, and network devices (Windows Server, desktops, switches, firewalls, Wi‑Fi). Respond to and resolve Level 2/3 support tickets and escalations. Plan, design, and implement infrastructure projects such as server builds, virtualization, cloud migrations, and security improvements. Manage Microsoft 365 and related cloud services (Exchange Online, Teams, SharePoint, Intune), including migrations and ongoing administration. Configure and support Active Directory, Group Policy, DNS, DHCP, VPN, and remote access solutions. Maintain backup and disaster recovery solutions, regularly verify backups, and participate in restoration testing. Ensure systems are patched, secure, and compliant with best practices and client policies. Document configurations, procedures, and project work; contribute to internal knowledge base. Collaborate with project managers, vendors, and internal teams; provide guidance to junior engineers as needed. Required Skills and Experience: Several years of experience in systems engineering or administration, ideally in an MSP or multi‑client environment. Strong knowledge of Windows Server, Active Directory, Group Policy, DNS, DHCP, and Microsoft 365. Experience with virtualization platforms (VMware vSphere/ESXi, Hyper‑V). Solid understanding of networking fundamentals: VLANs, VPNs, routing, switches, and firewalls. Familiarity with backup/DR tools and RMM/PSA platforms (e.g., Datto, Veeam, ConnectWise, Autotask). Strong troubleshooting, documentation, and customer service skills, with the ability to manage multiple client environments at once. Preferred Qualifications: Scripting/automation experience (PowerShell). Exposure to Azure AD, Azure IaaS, and security best practices (MFA, endpoint protection). Relevant certifications (e.g., Microsoft, VMware, Cisco, security).