Red Cup IT, Inc.

We are looking for a Staff Security Engineer at a Managed Service Provider (MSP) who is a high-level technical leadership role. Unlike a standard Security Engineer who might focus on a single organization’s perimeter, a Staff Engineer at an MSP must design, oversee, and scale security solutions across hundreds of diverse client environments. They act as the "architect-in-chief," balancing deep technical execution with high-level strategy and mentorship. Core Responsibilities At the Staff level, the focus shifts from "doing the work" to "defining how the work is done" across the entire MSP fleet. 1. Security Architecture & Strategy - Scalable Standard Operating Procedures (SOPs): Design security baselines (NIST, CIS, or ISO 27001) that can be applied to clients ranging from small dental offices to mid-market enterprise firms. - Tooling Selection: Evaluate and select the "MSP Stack"—SIEM/MDR platforms, EDR/XDR solutions, and automated vulnerability scanners—ensuring they support multi-tenancy. - Product Development: Partner with the Product or Sales teams to build new "Security-as-a-Service" offerings (e.g., vCISO services or Managed Phishing Simulation). 2. High-Level Technical Leadership - Tier 4 Escalations: Act as the final point of escalation for complex security breaches or persistent threats that Tier 1–3 analysts cannot resolve. - Automation & Scripting: Write advanced scripts (Python, PowerShell, Bash) to automate threat hunting and remediation across thousands of endpoints simultaneously. - Cloud Security Mastery: Secure multi-cloud environments (Azure, AWS, GCP) for clients, ensuring proper identity management (MFA/Conditional Access) and data encryption. 3. Mentorship & Governance - Team Upskilling: Mentor Junior and Senior Engineers, conducting code reviews and architectural deep-dives. - Compliance & Auditing: Lead clients through regulatory audits (HIPAA, GDPR, PCI DSS) and ensure the MSP itself remains compliant (SOC2). Required Skills & Qualifications A Staff Engineer is expected to have 8–12+ years of experience in IT and Security. CategoryKey RequirementsTechnical DepthMastery of EDR/XDR, SIEM (e.g., Sentinel, Splunk), Firewalls (Fortinet, Palo Alto), and Identity (Azure AD/Entra ID).Cloud ExpertiseDeep knowledge of cloud-native security tools and Zero Trust architecture.DevelopmentProficiency in Python or PowerShell for API integrations and security automation.Soft SkillsAbility to explain "zero-day" risks to non-technical business owners (CEOs/CFOs).CertificationsCISSP (highly preferred), CISM, CCSP, or advanced provider certs (AZ-500, PCNSE).

We are looking for a Staff IT Engineer who is responsible for the technical health of the MSP's entire client base. You aren't just fixing a server; you are designing the standard blueprint for how servers are deployed across 50 different companies. You serve as the bridge between business goals and technical execution, reporting typically to the CTO or Director of Engineering. Key Responsibilities 1. Technical Strategy & Standardization - Blueprint Design: Develop "Gold Standards" for client environments (e.g., standardizing Entra ID configurations or Intune policies across all tenants). - Platform Engineering: Manage and optimize the MSP's core toolset (RMM, PSA, Backup portals, and Documentation platforms). - Technology Roadmap: Evaluate emerging tech (like AI-driven helpdesk automation) and decide if/how to integrate it into the service offering. 2. High-Level Architecture & Escalation - Tier 4 Support: Act as the final "buck stops here" point for the most catastrophic or persistent technical issues. - Project Architecture: Design complex migrations (Cloud-to-Cloud, M&A integrations) that Senior Engineers then execute. - Root Cause Analysis (RCA): Lead investigations into systemic failures to ensure they never happen again across any client site. 3. Mentorship & Team Development - Multiplier Effect: You are measured by how much better you make the other engineers. You conduct code/script reviews and technical workshops. - Documentation Standards: Define how the team documents environments to ensure "Single Pane of Glass" visibility. 4. Security & Compliance - Hardening: Oversee the implementation of zero-trust frameworks and MFA across the entire MSP stack. - Audit Readiness: Ensure client environments meet regulatory standards (HIPAA, CMMC, SOC2) through automated auditing. Required Skills & Qualifications CategoryRequirementExperience8–12+ years in IT, with at least 5 years specifically in an MSP environment.Cloud MasteryExpert-level knowledge of Microsoft 365 (Enterprise), Azure (Identity & Networking), and AWS.AutomationProficiency in PowerShell, Python, or API integrations to "automate the boring stuff."SecurityExperience with EDR/XDR, SIEM, and Advanced Threat Protection.Soft SkillsAbility to explain $100k architectural decisions to non-technical CEOs (The "Business-to-Tech" translator). Typical Certifications (2026 Standards) - Microsoft: MS-102 (M365 Administrator Expert) or AZ-305 (Azure Solutions Architect). - Security: CISSP, CISM, or advanced vendor certs (e.g., Palo Alto PCNSE). - Frameworks: ITIL v4 or specialized MSP-centric management training.

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).

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.

We are looking for an MSP Technical Project Manager is responsible for planning, executing, and delivering IT projects for multiple managed services clients, ensuring they are completed on time, within scope, and within budget while meeting quality and customer satisfaction goals. This role serves as the primary liaison between clients, internal technical teams, and vendors, translating business requirements into actionable technical plans in a fast‑paced managed services environment. Key Responsibilities - Lead end‑to‑end delivery of multiple concurrent IT projects (infrastructure, cloud, security, and application initiatives) for MSP clients from initiation through deployment and handoff. - Develop and maintain comprehensive project plans, including scope, timelines, resource allocation, dependencies, and budgets. - Facilitate requirements gathering with clients and internal stakeholders; document business and technical requirements and translate them into clear deliverables and work packages. - Coordinate cross‑functional technical teams (engineers, service desk, networking, cloud, security, and vendors) to ensure timely, high‑quality project execution. - Monitor project progress, manage risks and issues, and proactively adjust plans, schedules, and resources to keep projects on track. - Maintain regular client communication, including status reports, expectation setting, scheduling of onsite/remote work, and management of escalations. - Own project documentation such as statements of work, change orders, schedules, status reports, acceptance criteria, and handover documentation to operations/support teams. - Ensure all projects follow standardized MSP project management methodologies, internal processes, and documentation standards. - Manage scope and change control to prevent scope creep, including impact analysis and approval of changes. - Track and report key project metrics (milestones, budget, profitability, risks, and customer satisfaction) to leadership and stakeholders. - Collaborate with account management and sales to provide project estimates, contribute to proposals, and identify follow‑on opportunities and roadmap items for clients. - Lead post‑project reviews and lessons learned to improve future MSP delivery practices and internal processes. - Work with third‑party vendors and partners on technology implementations, ensuring alignment with project goals and client standards. Qualifications - Bachelor’s degree in Information Technology, Computer Science, Engineering, Business, or related field, or equivalent experience. - 3–5+ years of experience managing technical/IT projects, with at least 2 years in a managed service provider or similar multi‑client environment preferred. - Strong understanding of IT infrastructure, networking, cloud services, and common MSP toolsets (RMM, PSA, ticketing platforms). - Proven experience managing multiple concurrent projects with competing priorities and deadlines. - Hands‑on experience with project management methodologies (Agile, Scrum, Waterfall) and tools (e.g., Jira, Asana, MS Project, or similar). - Excellent client‑facing, communication, and stakeholder management skills, including experience presenting status and risks to non‑technical audiences. - Strong analytical, problem‑solving, and risk‑management skills, with the ability to adapt plans when issues arise. - Relevant certifications such as PMP, PRINCE2, or Agile/Scrum are a plus. Skills - Project management: planning, scheduling, budgeting, resource management, risk management. - Technical aptitude: familiarity with infrastructure, networking, cloud platforms, and security concepts used in MSP environments. - Communication & leadership: cross‑functional coordination, conflict resolution, and facilitation of meetings and workshops. - Process orientation: ability to follow and improve MSP delivery processes, documentation standards, and quality controls.

We are looking for an MSP Service Desk Manager is responsible for leading the service desk team, overseeing day‑to‑day support operations, and ensuring consistent, high‑quality service delivery to all managed services clients. They own the service desk processes, metrics, and escalation paths to maintain SLA compliance and an excellent end‑user experience. Key Responsibilities - Lead, coach, and develop a team of Level 1–3 service desk technicians, including hiring, training, scheduling, performance management, and mentoring. - Oversee daily service desk operations, including ticket intake, assignment, prioritization, escalation, and resolution across all client environments. - Maintain and improve SLA compliance by monitoring queues, workloads, and response/resolution times, and by implementing corrective actions when needed. - Design, implement, and continuously refine service desk processes, including incident, request, problem, and change handling aligned with ITIL/ITSM best practices. - Act as the primary escalation point for complex or high‑impact incidents, including security events and major outages, coordinating internal and vendor resources to restore service quickly. - Manage customer communications for critical incidents and dissatisfied clients; handle complaints, reset expectations, and drive long‑term customer satisfaction. - Develop, maintain, and enforce documentation for standard operating procedures, knowledge base articles, and onboarding/offboarding processes for both staff and clients. - Monitor and analyze service desk metrics and trends (ticket volume, categories, aging, first contact resolution, CSAT, etc.) and provide regular reports to leadership with recommendations for improvement. - Coordinate closely with project, NOC, security, and account management teams to ensure smooth handoffs, effective change/release activities, and alignment with client roadmaps and agreements. - Ensure effective use, configuration, and governance of RMM, PSA, and related ITSM tools used for ticketing, monitoring, documentation, and reporting. - Drive a culture of continuous improvement, standardization, and automation to increase efficiency and reduce recurring incidents. Qualifications - 3–5+ years of experience in an MSP or similar managed services environment, including prior hands‑on service desk/support experience. - 2+ years in a leadership or supervisory role managing a technical support/service desk team. - Strong understanding of ITSM/ITIL processes (incident, problem, change, request); ITIL certification is preferred. - Broad technical knowledge of Windows Server/AD, Microsoft 365, networking fundamentals, endpoint management, backup/DR, and common MSP toolsets (RMM/PSA). - Proven ability to manage SLAs, handle escalations, and communicate clearly with both technical and non‑technical stakeholders, including executives and end users. - Strong analytical, organizational, and leadership skills, with demonstrated success using metrics and feedback to improve operations. Core Competencies - People leadership and coaching - Customer service and conflict resolution - Process design and continuous improvement - Incident and major incident management - Time management and prioritization in a high‑volume MSP environment

Role Description We are looking for an IT Support Engineer who is responsible for providing technical assistance to users, maintaining computer systems, troubleshooting hardware and software issues, and ensuring the smooth operation of an organization's IT infrastructure. - Technical Support - Provide first-line and second-line technical support to employees or customers. - Diagnose and resolve hardware, software, network, and system issues. - Respond to help desk tickets, emails, and phone support requests. - System & Device Management - Install, configure, and maintain desktops, laptops, printers, and mobile devices. - Set up user accounts, permissions, and access controls. - Manage operating systems such as Microsoft Windows, macOS, or Linux. - Network Support - Troubleshoot network connectivity issues (LAN, Wi-Fi, VPN). - Maintain routers, switches, and firewalls. - Monitor network performance and uptime. - Software & Application Support - Install and update applications and productivity tools like Microsoft 365 or Google Workspace. - Troubleshoot application errors and compatibility issues. - Documentation & Ticketing - Log issues and resolutions in ticketing systems such as ServiceNow, Jira Service Management, or Zendesk. - Maintain documentation for troubleshooting procedures and system configurations. - Security & Compliance - Implement security policies, patch updates, and antivirus solutions. - Support identity and access management. - Assist with incident response and security monitoring. Qualifications - Strong troubleshooting and diagnostic skills - Knowledge of operating systems (Windows, macOS, Linux) - Networking basics (TCP/IP, DNS, DHCP, VPN) - Experience with help desk or ticketing systems - Customer service and communication skills - Time management and problem-solving ability Requirements - Bachelor's degree in information technology, Computer Science, or related field - Certifications such as: - CompTIA A+ - CompTIA Network+ - Microsoft Certified certifications - Cisco Systems CCNA