Careers

Technical Specialist – Managed IT Support

Company Description

Southshore Managed IT Group provides managed IT, cloud, security, and consulting services to small and medium-sized businesses across Chicagoland, Northwest Indiana, and the Michiana region. We focus on delivering reliable, responsive IT support tailored to each client’s environment. Our team values teamwork, honesty, and integrity, and we aim to build long-term relationships through consistent, high-quality service.

Role Overview

We are seeking a Technical Specialist based in Portage, IN to support client IT environments through troubleshooting, system maintenance, and onsite service delivery. This role combines remote support with regular onsite client visits.

You will be responsible for diagnosing technical issues, implementing solutions, and ensuring client systems remain stable, secure, and operational.

This position includes travel to client sites. A valid driver’s license, reliable transportation, and the ability to travel independently are required. Personal vehicle use for local travel may be necessary.

This role includes a 60–90 day introductory evaluation period. During this time, performance, technical ability, communication, and client interaction will be assessed before transitioning into a permanent full-time role.

Key Responsibilities

• Provide remote and onsite technical support for client systems
• Troubleshoot hardware, software, networking, and cloud issues
• Respond to service requests and resolve tickets efficiently
• Support client infrastructure and ensure system uptime
• Communicate clearly with clients and internal team members
• Escalate complex issues appropriately when needed
• Document work and maintain accurate service records

What We’re Looking For

• Strong troubleshooting and analytical skills
• Ability to research solutions and resolve issues independently
• Clear communication with technical and non-technical users
• Experience with IT support, networking, and infrastructure environments
• Familiarity with cloud platforms and business IT systems
• Ability to prioritize tasks in a fast-paced environment

Core Traits for Success

• Takes initiative and ownership of issues
• Knows when to collaborate or escalate appropriately
• Reliable in client-facing environments
• Strong attention to detail and follow-through
• Adaptable and willing to learn new technologies

What We Offer

• Compensation based on experience and qualifications
• Paid time off and company-observed holidays
• Health and dental insurance reimbursement
• Retirement plan benefits
• Professional development, training, and certification support
• Opportunities to work with a diverse range of technologies and client environments

Preferred Qualifications

• 2 yrs relevant experience with Phone Support and Onsite Customer Service
• Bachelor’s degree in IT, Computer Science, or related field (preferred, not required)
• Certifications such as CompTIA A+, Network+, or equivalent experience

A Note to Applicants

Thank you for your interest in Southshore Managed IT Group. Please click the link below to apply.

All applications are reviewed by a member of our team, and we aim to provide updates throughout the hiring process.