IT Support Technician – Tier 2

Location: Oklahoma City, OK / Amarillo, TX
Employment Type: Full-time, On-site
Travel & On-Call: Minimal travel with occasional rotating on-call participation

Why Cultivate IT?

At Cultivate IT, we partner with growing businesses to solve real-world technology challenges, modernize their environments, strengthen security, and deliver peace of mind through reliable IT support. We are a Microsoft-focused Managed Services Provider with a cloud-first, security-first mindset. Our team works heavily across Microsoft 365, Azure, automation, infrastructure, and operational best practices to support a wide range of client environments. This role is a great fit for someone who enjoys solving complex technical issues, taking ownership of escalations, improving processes, documenting what they learn, and helping junior technicians grow.

What You'll Do

• 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.

What You Bring

Required

• 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, switching, 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.

Nice to Have

• Experience with Hyper-V, VMware, Proxmox, or other virtualization platforms.
• Experience with Azure Virtual Desktop or traditional RDS environments.
• Experience with NinjaOne, ConnectWise Manage, or similar RMM / PSA tools.
• Experience with firewalls, managed switches, wireless platforms, and network monitoring tools.
• PowerShell scripting or automation experience.
• Exposure to automation workflows, API integrations, or process improvement projects.
• Experience with cloud migrations, infrastructure projects, security hardening, and endpoint management.
• Network+, Security+, Microsoft, Azure, or equivalent certifications.
• Prior MSP experience supporting multiple clients and environments.

Security Expectations

Security is part of how we operate, not an afterthought. A strong candidate should be comfortable working with and learning more about:

• Multi-Factor Authentication
• Identity and access management
• Least privilege access principles
• Endpoint protection and device compliance
• Microsoft security features and best practices
• Security awareness and risk reduction
• Secure documentation and operational standards

What Success Looks Like

• You take ownership of escalated issues and follow them through to resolution.
• You troubleshoot efficiently and independently while knowing when to escalate.
• You communicate clearly with clients, teammates, and leadership.
• You document your work in a way that helps the whole team improve.
• You help reduce recurring issues by identifying root causes and recommending better long-term solutions.
• You contribute to automation, process improvement, and operational consistency.
• You support and mentor junior technicians without losing focus on your own technical growth.
• You embrace Microsoft cloud technologies and modern IT operations.

Benefits

• 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 — from impromptu happy hours to holiday parties