Sr. Helpdesk Specialist

HALO CENTERS LLC is hiring a Sr. Helpdesk Specialist to serve as the technical lead for daily IT support and escalations at our Sarasota, FL onsite location. This role combines hands-on troubleshooting with ownership of ticket performance, service levels, and core identity and device administration across Active Directory, Microsoft 365, Entra ID, Exchange Online, and Microsoft Intune.

What You’ll Own

• Act as the escalation point for Level I and junior staff, resolving escalated hardware, software, access, and network issues, and performing root-cause analysis.
• Own assigned ticket queues, including queue health and response and resolution targets, with attention to urgent-ticket SLAs.
• Document escalations clearly and escalate to IT leadership when needed, with focus on repeatable process improvements.
• Provide remote support to users using TeamViewer.

Core Systems and Security Responsibilities

• Administer on-premises Active Directory servers, including user and group management, group policy, and access permissions, and keep them aligned with Entra ID.
• Manage mailboxes, shared mailboxes, distribution lists, mail flow, licensing, and tenant settings within Exchange Online.
• Manage Entra ID accounts, including multi-factor authentication, conditional access, and application access controls.
• Deploy, configure, and manage devices through Microsoft Intune, including compliance and configuration policies, app deployment, and device enrollment.
• Configure, troubleshoot, and maintain Wi-Fi and related connectivity, including VPN, with grounding in networking fundamentals such as TCP/IP, DNS, and DHCP.

Hands-On IT Operations

• Support new hires by handling procurement, configuration, shipping, and tracking of hardware.
• Ensure new hires are ready on day one, securely disable accounts, and recover equipment during offboarding.
• Support patching, device compliance, access reviews, and provide the IT documentation required for audits.
• Maintain and update IT equipment and software inventory.

Mentoring and Documentation

• Train and guide junior specialists and interns.
• Maintain procedures and knowledge base articles to support consistent support operations.

What You Bring

• Hands-on experience administering on-premises Active Directory servers.
• Strong experience with Microsoft 365, including Exchange Online administration.
• Experience with Microsoft Entra ID, including MFA, conditional access, and application access.
• Experience with Microsoft Intune, including device enrollment, compliance and configuration policies, and app deployment.
• Hands-on experience using TeamViewer for remote support.
• Experience configuring and troubleshooting wireless networks, with networking fundamentals (TCP/IP, DNS, DHCP, VPN).
• Working knowledge of Windows and macOS and hardware troubleshooting.
• Security awareness, including careful handling of sensitive and health information.
• Experience with ticketing systems (such as Jira Service Management) and managing to SLAs.
• Strong communication skills, plus the ability to mentor others and manage multiple priorities.

Nice to Have

• Plus: PowerShell scripting experience.
• Plus: Experience with AWS and/or GCP.

Minimum Qualifications

• Education: Associate's or Bachelor's degree in Information Technology, Computer Science, or a related field preferred, or equivalent hands-on experience.
• Experience: 5 or more years of experience in IT support or systems administration, including managing Active Directory and Microsoft 365 in a multi-site environment.

Technologies You’ll Work With

Active Directory, Microsoft 365, Entra ID, Exchange Online, Microsoft Intune, TeamViewer, Wi-Fi, VPN, TCP/IP, DNS, DHCP, Windows, macOS, Jira Service Management, PowerShell, AWS, GCP.

Compensation and Location

Location: Sarasota, FL (onsite).
Pay: USD 27 to 41 per hour.

Travel

Occasional travel may be required for onsite support.