IT Support Specialist

gobravvo; Oak Park (IL); On-site; USD 60,000 - 85,000; Full time

Job summary

gobravvo seeks an IT Support Specialist to provide tier-1 and tier-2 IT support in Oak Park, IL. You will assist end users, manage onboarding, and ensure SLA adherence while maintaining Windows Server, AD, Exchange, and network infrastructure.

Ideal candidates bring hands-on MSP experience, strong communication, and proficiency with RMM tools and VPN design. This role offers growth in a dynamic tech-focused firm with a strong client-service orientation.

Qualifications

• 4+ years hands-on experience configuring, troubleshooting networking, Windows servers/workstations, Exchange, and AD.
• 2–3 years in a client-facing environment such as sales engineering or technical consulting.
• Familiarity with Kaseya RMM and Autotask PSA is advantageous.
• Strong communication, organization, and time-management abilities.

Responsibilities

• Provide first and second-level support via phone, portal, and email with timely resolutions.
• Oversee onboarding: provisioning and system setup for new employees.
• Prioritize incidents per SLAs and ensure service quality.
• Use remote tools to diagnose and resolve end-user issues efficiently.
• Design, deploy, and maintain VPNs and encryption solutions.
• Monitor Windows OS and server environments; apply updates and security patches.
• Maintain servers, AD, DNS, DHCP, and file/print services.
• Manage WAN/LAN, TCP/IP, firewalls, routers, and switches for security and performance.
• Install antivirus and maintain current definitions across systems.
• Configure and support VOIP and Exchange server environments.
• Analyze event logs and respond to escalated requests with advanced troubleshooting.

Skills

Communication

Customer service

Time management

Problem solving

Teamwork

Education

CompTIA Network+

CompTIA Security+

MCITP

MCSA

CCNA/CCIE

Tools

Kaseya RMM

Autotask PSA

RMM tools

Active Directory

Exchange Server

VPN

Job description

IT Support Specialist

Job Overview

Our client, a prominent IT solutions provider in Oak Park, IL, is seeking a skilled IT Support Specialist for a full-time position. The IT Support Specialist plays a critical role in ensuring the smooth operation and functionality of organizational IT systems. This position is responsible for responding to technical support requests, serving as the primary contact for IT service desk tickets, maintaining system integrity, and contributing to end-user satisfaction through effective technical solutions. Working as an IT Support Specialist in Oak Park, IL, offers the opportunity to be part of a dynamic and innovative business community.

Key Responsibilities

• Provide first and second-level support for incoming requests to the IT service desk, utilizing telephone, web portal, and email channels to deliver courteous and timely resolutions for end-user issues.
• Oversee onboarding processes for new employees, including provisioning and system setup to ensure seamless integration into the organizational IT environment.
• Effectively prioritize incidents and service requests according to established processes, ensuring adherence to defined service level agreements (SLAs).
• Utilize remote access tools and diagnostic utilities to troubleshoot and resolve end-user technical issues efficiently.
• Design, administer, and support VPN infrastructure, including point-to-point (PTP), client-based, encrypted, and IPsec solutions.
• Monitor and manage Microsoft Windows operating systems (Windows 7, 8, 10), ensuring systems are secure and up-to-date.
• Administer Microsoft Windows Server environments (2003, 2008, 2012), Small Business Server (2003, 2008, 2012), and Exchange Server (2003, 2007, 2010).
• Support and maintain WANs, LANs, TCP/IP networks, firewalls, routers, and switches to optimize network security and performance.
• Perform server administration tasks, including management of Active Directory, File & Print services, DNS, and DHCP.
• Install and update antivirus software, maintaining current virus definitions to protect IT assets.
• Optimize and maintain network hardware and software, ensuring organizational IT resources operate efficiently and reliably.
• Build, deploy, and maintain file servers and cloud computing solutions, contributing to the organization's digital transformation.
• Configure and deploy VOIP solutions to enhance communication infrastructure.
• Administer and manage Microsoft Exchange Server environments to ensure reliable email communication.
• Monitor system alert tools and execute appropriate actions in alignment with organizational guidelines.
• Analyze event logs to diagnose and resolve system issues proactively.
• Respond to escalated service requests requiring advanced technical expertise and troubleshooting skills.

Qualifications & Requirements

• At least four years of hands‑on experience configuring, troubleshooting, and repairing networking equipment, Windows servers and workstations, Exchange server, and Active Directory environments.
• Two to three years of experience in a client‑facing environment, such as sales engineering or technical consulting.
• Familiarity with Kaseya RMM and Autotask PSA platforms is considered advantageous.
• Exceptional verbal and written communication skills, with the ability to interact effectively at a business level and understand client technology needs.
• Strong organizational and time‑management abilities to handle multiple priorities and meet deadlines.
• Experience in drafting technical proposals and implementing IT solutions to address business requirements.
• Proven track record as a reliable, results‑oriented, and collaborative team player.
• Comprehensive understanding of technology and business productivity systems.
• Experience with remote monitoring and management (RMM) tools is a plus.
• Advanced problem‑solving skills, outstanding customer service orientation, and proficiency in multitasking and organization.
• Sales training experience is an asset.
• Experience working in a managed service provider (MSP) environment is highly desirable.

Preferred Certifications (Not Required)

• CompTIA Network+ and/or CompTIA Security+ certifications
• MCSA (Microsoft Certified Solutions Associate), MCSE (Microsoft Certified Solutions Expert), or MCITP (Microsoft Certified IT Professional)
• CCNA or CCIE (Cisco Certified Network Associate/Expert) certifications are highly valued

Career Development

The IT Support Specialist role offers challenging work, opportunities for career advancement, a positive work environment, and access to ongoing training and professional development.