Tier 2 Tech Support Agent Jobs (NOW HIRING)

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

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.

• 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.

• 35 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.

• 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 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

• 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.

• 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

Cultivate IT is an Equal Opportunity Employer. We consider applicants for all positions without regard to race, color, religion, sex, national origin, veteran status, disability, or any other legally protected status.