Senior IT Specialist

Oasis Landscape Services Inc•Gainesville, FL

10h•Hybrid

About The Position

The Senior IT Specialist serves as the primary hands-on technology resource for OASIS Infrastructure Asset Management, supporting highway and road maintenance operations across the states where OASIS operates. This role is responsible for maintaining a reliable IT infrastructure, supporting approximately 300 employees across 15+ project locations, and ensuring that both office and field personnel have the tools and systems they need to perform their work safely and efficiently. This position handles day-to-day IT operations, including helpdesk support, Microsoft 365 administration, network troubleshooting, device management, and field technology support for systems such as Samsara telematics, GPS tracking, and dashcam platforms. The Senior IT Specialist works closely with all departments to keep systems running, resolve issues quickly, and support OASIS’s ongoing transition from paper-based processes to digital workflows. 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 projects where OASIS establishes operations.

Requirements

Solid understanding of network infrastructure, including LAN/WAN, Wi-Fi, VPN, firewalls, and DNS/DHCP
Working knowledge of Microsoft 365 administration, including Exchange Online, SharePoint, Teams, Entra ID, and Intune
Knowledge of cybersecurity best practices, endpoint protection, and data backup procedures
Familiarity with Windows and Mac operating systems, Active Directory, and group policy management
Understanding of VoIP phone systems and mobile device management platforms
Basic knowledge of cloud services (Azure) and hybrid on-premises/cloud environments
Familiarity with fleet telematics systems (Samsara, Verizon Connect, Geotab, or equivalent)
Understanding of GPS tracking, dashcam, and electronic logging device (ELD) platforms
Awareness of rugged device deployment and field technology challenges in outdoor and highway work zone environments
Basic understanding of DOT contract technology requirements and compliance documentation
Proficiency in troubleshooting hardware, software, network, and connectivity issues across office and field environments
Skill in administering a Microsoft 365 tenant, managing user accounts, licenses, and security groups
Skill in configuring and deploying desktops, laptops, tablets, mobile devices, and peripheral equipment
Proficiency in SharePoint site management, document library configuration, and basic Power Platform support
Skill in maintaining IT asset inventory, procurement processes, and lifecycle tracking
Skill in documenting systems, procedures, and user guides in clear, accessible language
Ability to explain technical concepts in plain language to non-technical users at all levels, from field crews to executive leadership
Strong customer service orientation with patience and professionalism when supporting diverse user skill levels
Effective written communication for creating user documentation, training materials, and status reports
Ability to build productive working relationships across geographically dispersed office and field teams
Collaborative approach to working with other departments, including HR, Operations, Safety, Fleet, and Finance
Strong organizational abilities withthe capacity to manage multiple support requests and priorities simultaneously
Attention to detail in documentation, configuration management, and security compliance
Effective problem-solving skills with the ability to diagnose and resolve issues under time pressure
Self-directed work style with the ability to prioritize tasks and manage time across competing demands
Process improvement mindset with the ability to identify recurring issues and implement lasting solutions
Ability to support 24/7 field operations, including occasional after-hours response for critical system failures
Associate’s degree in Information Technology, Computer Science, Network Administration, or related field
OR High school diploma/GED with 5+ years of progressive IT experience demonstrating equivalent knowledge
OR Technical certifications (CompTIA A+, Network+, Security+, or Microsoft certifications) with 4+ years of hands-on IT experience
Minimum 4 years of hands-on IT support experience with direct responsibility for end-user support, infrastructure maintenance, and system administration
Demonstrated experience supporting a multi-site organization with both office and field-based employees
Proven experience with Microsoft 365 administration, including user management, SharePoint, and Teams
Experience in troubleshooting network issues, managing hardware deployments, and maintaining IT documentation
History of providing helpdesk support with a track record of timely issue resolution and strong customer satisfaction
Experience managing IT vendor relationships and coordinating with external service providers
Valid driver’s license with clean driving record (required for travel to project sites)
Ability to travel up to 20% of the time to project locations across Florida, South Carolina, Virginia, or where OASIS establishes new operations.
Availability to respond to critical IT emergencies outside regular business hours as needed
Must pass background check and drug screening per company policy
Comfortable working in both office environments and field locations, including project offices, equipment yards, and job sites
Able to transport IT equipment weighing up to 40 pounds

Nice To Haves

Bachelor’s degree in Information Technology, Computer Science, or related field
Professional certifications: CompTIA A+, CompTIA Network+, CompTIA Security+, Microsoft Certified: Modern Desktop Administrator, Microsoft 365 Certified: Administrator, or ITIL Foundation
5+ years of IT experience in construction, infrastructure, highway maintenance, government contracting, or field service industries
Experience supporting fleet telematics, GPS tracking, and dashcam systems (Samsara, Verizon Connect, Geotab)
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
Bilingual (English/Spanish) a plus, given workforce demographics

Responsibilities

Serve as the primary point of contact for all IT support requests from corporate, regional, and field employees across all locations
Troubleshoot and resolve hardware, software, network, and connectivity issues for both office and field personnel
Manage employee onboarding and offboarding technology workflows, including account setup, equipment deployment, and access termination
Provide remote and on-site support for employees working at project offices, equipment yards, and field locations
Create and maintain user guides, how-to documentation, and training materials for common systems and tools
Deliver technology orientation for new hires, including field-specific systems, mobile devices, and safety platforms
Track and prioritize support requests, ensuring timely resolution with emphasis on safety-critical and operations-impacting issues
Administer the Microsoft 365 tenants, including Exchange Online, SharePoint Online, Teams, OneDrive, and Entra ID (Azure AD)
Manage user accounts, security groups, licenses, and permissions across the organization
Maintain SharePoint sites, document libraries, and permission structures supporting departmental workflows
Support Power Apps, Power Automate, and Power BI solutions used by HR, operations, and finance
Assist with enterprise application support, including HRIS/payroll systems, accounting software, and performance management platforms
Monitor software licensing compliance and coordinate renewals
Maintain and troubleshoot network infrastructure across corporate offices, regional project offices, and field locations
Support server environments, including on-premises and cloud-based systems (Azure, Microsoft 365)
Manage internet connectivity, Wi-Fi access points, VPN configurations, and firewall settings at all locations
Set up and configure network connectivity at new project sites, field offices, and temporary work locations
Coordinate with internet service providers and telecommunications vendors to resolve outages and service issues
Maintain VoIP phone systems and mobile device management (MDM) across all locations
Implement and monitor endpoint protection, email security, multi-factor authentication, and access controls across all devices
Conduct regular security updates, patching, and firmware upgrades on all systems and devices
Monitor for security threats, investigate suspicious activity, and escalate incidents as appropriate
Manage data backup systems and verify the recoverability of critical business data through regular testing
Support employee cybersecurity awareness through training, phishing simulations, and best practice communications
Maintain documentation of security configurations, access controls, and incident response procedures
Support and maintain fleet telematics systems (Samsara or equivalent), GPS tracking, and dashcam platforms used across field operations
Deploy, configure, and troubleshoot rugged mobile devices, tablets, and laptops for field crews working in highway work zones and outdoor environments
Support field-specific applications, including work order management, digital timekeeping, digital forms, and photo documentation tools
Coordinate with Operations, Safety, and Fleet teams to resolve technology issues impacting field productivity and compliance
Ensure field equipment is durable, properly configured, and appropriate for crews working in active roadway and construction environments
Support electronic logging devices and DOT compliance technology as needed
Maintain an accurate inventory of all IT assets, including computers, mobile devices, monitors, printers, networking equipment, and peripherals
Manage equipment procurement, deployment, and lifecycle replacement for both office and field hardware
Coordinate with IT vendors, service providers, and managed service partners for specialized support and project work
Research and recommend technology solutions to improve operations, reduce costs, or address recurring issues
Track IT expenditures and assist with budget planning for hardware, software, and service contracts
Maintain accurate documentation of network architecture, system configurations, standard operating procedures, and vendor contacts
Develop and update IT policies and procedures for end-user standards, acceptable use, and equipment handling
Support OASIS’s digital transformation by helping convert paper-based processes into digital workflows using SharePoint, Power Apps, and other M365 tools
Identify recurring issues and implement permanent fixes to reduce support volume and improve system reliability
Assist with IT-related compliance documentation for DOT contract audits and client requirements