IT Helpdesk Specialist (Tier 1 / Tier 2)

Oasis Landscape Services Inc • Gainesville, FL

19h • $22 - $24 • Hybrid

About The Position

The IT Helpdesk Specialist (Tier 1 / Tier 2) provides frontline and escalated technical support for OASIS employees across the states we serve. This position brings responsive, in-house end-user support capabilities to the company, reducing reliance on outsourced vendor services and recurring technology spend. This position works hand in hand with the IT Support Specialist and operates under that role's guidance and direction for day-to-day work assignments, ticket priorities, and technical standards. Hierarchically, the position reports to the VP/CFO for administrative and organizational matters. The IT Helpdesk Specialist serves as the first and second point of contact for day-to-day technology issues, from account and device setup through escalated hardware, software, and network troubleshooting. The role partners with and serves all departments across the company to keep employees productive, systems stable, and support requests resolved quickly and clearly. This position is suited to an experienced help-desk professional with proven Tier 1 and Tier 2 support skills, solid technical depth across Windows, Microsoft 365, endpoints, and networking, and a strong service orientation in a multi-site environment.

Requirements

• Proven Tier 1 and Tier 2 support skills across Windows, Microsoft 365, hardware setup, mobile devices, printers, and standard business software.
• Skill in diagnosing and resolving hardware, software, network, and connectivity issues efficiently, and in troubleshooting application bugs and performance.
• Working knowledge of Microsoft 365 administration, endpoint configuration, VPN, and basic networking (Wi-Fi, routers, switches, connectivity).
• Familiarity with help-desk and ticketing practices that keep issues tracked and resolved on time.
• Proficiency in Microsoft 365 applications, including Outlook, Word, Excel, Teams, and SharePoint, and ability to learn new platforms quickly.
• Ability to explain technical issues in plain language to employees at every level, from field crews to executive leadership.
• Strong customer-service orientation with patience, follow-through, and a sense of urgency.
• Effective written communication for documentation, instructions, and status updates.
• Collaborative working style that builds trust with all departments across the company and with outside vendors.
• Strong organizational ability to manage multiple support requests and project tasks at once without dropping commitments.
• Sound judgment to prioritize issues by business impact and escalate appropriately.
• Attention to detail in configuration, testing, and data handling.
• Ability to work independently with minimal supervision while keeping leadership informed.
• High school diploma or GED equivalent, plus relevant technical experience; OR an Associate's or Bachelor's degree in Information Technology, Computer Science, Management Information Systems, or a related field.
• Two or more years of combined Tier 1 and Tier 2 IT support experience.
• Proficiency in Microsoft 365 and Windows endpoint support.
• Strong analytical, troubleshooting, and customer-service skills.
• Valid driver's license with a satisfactory driving record.

Nice To Haves

• CompTIA A+, Network+, Security+, or Microsoft 365 / Azure certifications.
• Bachelor's degree in Information Technology, Computer Science, or Management Information Systems.
• Experience administering Microsoft 365 and managing user accounts and security in a business environment.
• Experience supporting multi-site or field-based operations, ideally in construction, infrastructure, highway maintenance, or government contracting.
• Bilingual English/Spanish.

Responsibilities

• Serve as the first point of contact for employee technology requests, responding promptly and tracking issues from intake through resolution.
• Resolve common end-user problems involving accounts, passwords, email, Microsoft 365, printing, mobile devices, and standard business applications.
• Set up, configure, and deploy laptops, desktops, monitors, phones, and peripherals for new hires and existing staff.
• Execute new-hire IT onboarding within Microsoft 365, including account setup, security group and distribution list membership, mailbox and device provisioning, and license assignment, in coordination with Human Resources.
• Execute employee-termination offboarding within Microsoft 365, including account deprovisioning, access and group removal, license reclamation, and mailbox or data handoff, in coordination with Human Resources.
• Provide clear, patient support to field and office employees across all locations, in person, by phone, and remotely.
• Diagnose and resolve escalated hardware, software, network, and connectivity issues that cannot be closed at Tier 1.
• Troubleshoot Microsoft 365 administration, endpoint configuration, VPN, Wi-Fi, and basic network connectivity across office and field sites.
• Coordinate with internet, telecom, and managed-service providers to resolve outages and service problems quickly, and implement permanent fixes for recurring issues.
• Optimize the performance of end-user devices and standard business applications, identifying root causes rather than repeating temporary workarounds.
• Manage user accounts, security groups, permissions, and access controls within Microsoft 365 under a least-privilege approach.
• Support periodic access reviews and role and permission standards, in coordination with Human Resources and the IT Support Specialist.
• Follow established security and configuration standards for endpoints, mobile devices, and user accounts, escalating security concerns immediately.
• Serve as the internal point of contact for software, hardware, and service vendors, managing tickets and holding providers accountable to service levels.
• Track software licenses, subscriptions, and renewals, flagging opportunities to consolidate cost or eliminate unused services.
• Support the transition away from outsourced IT support services, capturing knowledge and documentation from departing providers.
• Create and maintain clear documentation for IT procedures and common support resolutions so knowledge stays inside the company.
• Build a basic knowledge base and self-service resources that reduce repeat questions and speed up resolution.
• Provide training and guidance to business users on standard applications, devices, and technology tools.
• Maintain an accurate inventory of technology assets, licenses, and configurations, and report support volume, recurring issues, and system performance to the IT Support Specialist for consolidated reporting to leadership.
• Perform other duties as assigned to meet the ongoing needs of the organization.

Benefits

• Ability to travel up to 15% between OASIS locations for on-site support and projects, with occasional availability outside standard business hours for maintenance, deployments, or urgent issues.
• Must pass a background check and drug screening in accordance with company policy.
• Ability to handle confidential employee, financial, and business information with integrity and discretion.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: High school or GED