IT Support Specialist

Oasis Landscape Services Inc•Gainesville, FL

13d•Hybrid

About The Position

The IT Support Specialist provides technical support for end users, systems, and business applications across OASIS Infrastructure Asset Management. This role troubleshoots and resolves hardware, software, network, and connectivity issues, and helps maintain reliable systems supporting approximately 300 employees across 15 locations across the different states where OASIS operates. Working closely with all departments, this position maintains reliable IT operations for both office and field personnel in a highway and road maintenance environment. Responsibilities include endpoint management, Microsoft 365 administration, cybersecurity compliance, field technology support for systems such as Samsara telematics and GPS tracking, and proactive system monitoring to minimize downtime. This is a hybrid position based near one of OASIS’s Florida project locations in Gainesville, Ocoee, West Palm Beach, Ocala, or Pompano Beach, with travel to other project sites or future locations where OASIS establishes operations.

Requirements

Strong knowledge of Windows, macOS, Active Directory, group policy management, and network infrastructure (LAN/WAN, Wi-Fi, VPN, firewalls, DNS/DHCP)
Working knowledge of Microsoft 365 administration (Exchange Online, SharePoint, Teams, Entra ID, Intune) and cybersecurity best practices
Experience with ticketing systems, remote support tools, and endpoint management platforms (RMM, MDM)
Understanding of VoIP phone systems, mobile device management, and cloud services (Azure, hybrid environments)
Ability to troubleshoot hardware, software, network, and cloud service issues effectively
Excellent communication and documentation skills, with the ability to explain technical concepts in plain language to non-technical users at all levels
Strong customer service orientation with patience and professionalism when supporting diverse user skill levels
Effective organizational abilities with the capacity to manage multiple support requests and priorities simultaneously
Self-directed work style with ability to support 24/7 field operations, including occasional after-hours response for critical system failures
Associate’s degree in IT, Computer Science, Network Administration, or related field; OR high school diploma/GED with 4+ years of progressive IT experience; OR technical certifications (CompTIA A+, Network+, Security+, or Microsoft certifications) with 3+ years of hands-on IT experience
2–4 years of hands-on IT support in service desk or IT support roles with responsibility for end-user support, infrastructure maintenance, and system administration
Experience supporting a multi-site organization with both office and field-based employees; proven M365 administration experience
Track record of troubleshooting network issues, managing hardware deployments, maintaining IT documentation, and delivering strong customer satisfaction
Experience managing IT vendor relationships and coordinating with external service providers
Must be at least 23 years old (per company insurance requirements).
Must possess an active and valid Florida driver’s license with no restrictions and be able to pass a Motor Vehicle Record (MVR) check and maintain insurability under company policy.
Ability to travel up to 20% to project locations across the different projects, and future projects where OASIS establishes a presence
Availability to respond to critical IT emergencies outside regular business hours as needed
Compliance with the company's Drug and Alcohol Policy; able to pass pre-employment and random testing. A background check and job-related physical may be required.
Comfortable working in office and field environments, including project offices and job sites
Able to transport IT equipment weighing up to 40 pounds

Nice To Haves

CompTIA A+, Network+, or Security+; Microsoft 365 Certified: Administrator; Microsoft Certified: Modern Desktop Administrator; ITIL Foundation
3+ years of IT experience in construction, infrastructure, highway maintenance, government contracting, or field service industries
Experience with fleet telematics (Samsara, Verizon Connect, Geotab), GPS tracking, and dashcam systems
Experience with Power Platform (Power Apps, Power Automate, Power BI) and SharePoint site design
Background supporting organizations transitioning from paper-based to digital workflows
Experience deploying and managing rugged mobile devices in outdoor or construction environments
Background in organizations that have undergone growth, mergers, or geographic expansion
Experience supporting HRIS/payroll systems and enterprise business applications
Familiarity with government contract IT compliance and audit requirements

Responsibilities

Troubleshoot and resolve hardware, software, network, and account issues for office and field employees across all locations
Diagnose and resolve connectivity, authentication, and performance issues across office and field environments
Analyze recurring support trends and implement long-term solutions to reduce ticket volume; coordinate with vendors and ISPs when external resolution is required
Manage enterprise endpoint tools, including Microsoft Intune, MDM, RMM platforms, imaging, and patch management; maintain workstation standards and security baselines
Administer Microsoft 365 tenants, including Exchange Online, SharePoint, Teams, OneDrive, and Entra ID (Azure AD); support MFA, SSO, and conditional access policies
Deploy, configure, and lifecycle-manage desktops, laptops, tablets, rugged mobile devices, and peripherals; monitor software licensing compliance and coordinate renewals
Provide responsive, professional support to employees at all levels with minimal downtime
Document solutions, create knowledge base articles, and maintain user guides; deliver technology orientation for new hires, including field-specific systems and safety platforms
Ensure excellent customer satisfaction through clear communication, timely follow-up, and professional service delivery
Participate in incident response, problem management, and root cause analysis; monitor system health, logs, and alerts to proactively prevent issues
Manage employee onboarding/offboarding technology workflows, including account setup, equipment deployment, and access termination
Maintain accurate IT asset inventory; track expenditures and assist with budget planning for hardware, software, and service contracts
Support fleet telematics systems (Samsara or equivalent), GPS tracking, and dashcam platforms; deploy and troubleshoot rugged devices for field crews in highway work zones
Support field applications, including work order management, CMMS, digital timekeeping, digital forms, and photo documentation tools
Coordinate with Operations, Safety, and Fleet teams to resolve technology issues impacting field productivity; support ELD and DOT compliance technology as needed
Implement and monitor endpoint protection, e-mail security, MFA, and access controls; conduct regular patching and firmware upgrades on all systems
Monitor for security threats, investigate suspicious activity, and escalate incidents per established protocols
Manage data backup systems, verify recoverability through regular testing, and support cybersecurity awareness training and phishing simulations
Maintain documentation of network architecture, system configurations, SOPs, and vendor contacts; develop IT policies for end-user standards and equipment handling
Support OASIS’s digital transformation by converting paper-based processes into digital workflows using SharePoint, Power Apps, and M365 tools
Assist with IT-related compliance documentation for DOT contract audits and client requirements