Tier 2 IT Support Technician — MSP Cloud & Security

Cultivate IT; Oklahoma; On-site; USD 52,000 - 76,000; Full time

Benefits offered by this job

401(k) with 3% company match

Medical, Dental & Vision

HSA company contribution

Life & Disability Insurance

Flexible Work Hours & Generous PTO

Professional Development Stipend

Donut Friday & Quarterly Team Events

A Culture That Celebrates Wins

Job summary

Cultivate IT, a Microsoft-focused MSP, seeks an IT Support Technician — Tier 2 to support on-site client environments in Oklahoma City, OK and Amarillo, TX. You’ll escalate, troubleshoot across 365/Azure, Windows Server, and networking, and contribute to security and reliability improvements.

Key responsibilities include documenting procedures, mentoring Tier 1 staff, and participating in rotating on-call duties in a fast-paced MSP setting.

Qualifications

• 3–5 years of hands-on IT support, systems administration, or MSP experience.
• Strong troubleshooting ability across desktops, servers, networks, cloud services, and modern Microsoft environments.
• Experience administering Microsoft 365, including Exchange Online, Teams, SharePoint, Entra ID / Azure AD, and Intune.
• Working knowledge of Windows Server, Active Directory, DNS, DHCP, Group Policy, and file services.
• Solid understanding of networking concepts, including TCP/IP, VLANs, VPNs, routing, firewalls, and wireless infrastructure.
• Familiarity with Azure fundamentals, cloud identity, virtual machines, storage, networking, and security concepts.
• Experience supporting backup, disaster recovery, virtualization, and business continuity solutions.
• Strong written and verbal communication skills, including the ability to explain technical issues clearly to clients and teammates.
• Strong documentation habits and the ability to create useful troubleshooting notes, procedures, and technical standards.
• A proactive, ownership-focused mindset with a desire to improve systems, processes, and client outcomes.
• Comfort working in a fast-paced MSP environment supporting multiple client networks and business needs.

Responsibilities

• Serve as a technical escalation point for Tier 1 technicians and help resolve more complex support issues.
• Troubleshoot and resolve issues across Microsoft 365, Azure, Windows Server, endpoints, networking, cloud services, and client infrastructure.
• Administer Microsoft 365 environments, including Exchange Online, Teams, SharePoint, Entra ID, Intune, and related security features.
• Support Azure infrastructure and cloud-connected environments, including Azure fundamentals, Azure Virtual Desktop, identity, networking, and security best practices.
• Manage and troubleshoot Windows Server environments, including Active Directory, DNS, DHCP, Group Policy, file services, and related infrastructure.
• Configure, support, and troubleshoot networking environments, including firewalls, switches, wireless, VPNs, VLANs, routing, and network connectivity.
• Assist with backup, disaster recovery, and business continuity solutions.
• Participate in client onboarding, infrastructure upgrades, migrations, endpoint deployments, and internal projects.
• Create and maintain clear technical documentation, diagrams, troubleshooting steps, and internal standards.
• Identify recurring issues and recommend long-term improvements that increase reliability, security, and efficiency.
• Use PowerShell or other scripting tools where appropriate to automate repetitive tasks and improve operational workflows.
• Collaborate with engineers, project teams, and leadership on technical improvements and client outcomes.
• Mentor and support Tier 1 technicians by sharing knowledge, reviewing escalations, and contributing to a culture of technical growth.
• Participate in a rotating on-call schedule as needed.

Skills

Troubleshooting

Ownership mindset

Written and verbal communication

Mentoring

Time management

Tools

NinjaOne

ConnectWise Manage

PowerShell

Azure

Microsoft 365 admin

Hyper-V

Job description

Cultivate IT, a Microsoft-focused MSP, seeks an IT Support Technician — Tier 2 to support on-site client environments in Oklahoma City, OK and Amarillo, TX. You’ll escalate, troubleshoot across 365/Azure, Windows Server, and networking, and contribute to security and reliability improvements.

Key responsibilities include documenting procedures, mentoring Tier 1 staff, and participating in rotating on-call duties in a fast-paced MSP setting.