Help Desk Specialist Chicago, IL

Strongpoint Partners is a tech‑enabled retirement services platform serving small‑to‑mid‑sized businesses with integrated retirement third‑party administration, recordkeeping, payroll, and HR solutions. Recognized as one of Inc. 5000’s fastest‑growing private companies in America and certified as a Great Place to Work, Strongpoint offers a suite of services that prioritizes accuracy, compliance, and reduction of regulatory risk for its clients, delivered by local client success teams that understand the nuances of their markets.

Strongpoint Partners is seeking two highly motivated Help Desk Technicians to join our IT team. This role provides frontline technical support to end users and plays a key role in ensuring the reliable operation of hardware, software, and network systems. The ideal candidate is a strong troubleshooter with excellent communication skills and a customer‑first approach to problem‑solving.

This role follows a hybrid work model with the expectation of in‑office work approximately 2‑4 days per week from our Riverwoods, IL and/or downtown Chicago offices.

• Provide Tier 1 and Tier 2 technical support to end users, ensuring timely and effective resolution of issues.
• Troubleshoot and support Microsoft Office 365 applications and services.
• Build, configure, and deploy laptops managed through Microsoft Intune.
• Diagnose and resolve local network and VPN connectivity issues.
• Provision and manage user accounts in Office 365, including permissions and security settings.
• Ensure endpoint security tools and controls are active, compliant, and functioning properly.
• Maintain accurate hardware and software asset records within the ITSM system.
• Escalate high‑priority or complex incidents to management or higher‑level support as needed.
• Deliver exceptional customer service and communicate clearly with both technical and non‑technical users.
• Other duties as assigned.

• 3‑5+ years of proven experience in a Help Desk or IT Support role.
• Strong working knowledge of Office 365 administration and troubleshooting.
• Experience with Microsoft Intune or similar device management tools.
• Solid understanding of networking fundamentals, including VPN technologies.
• Familiarity with ITSM tools and asset management best practices.
• Ability to prioritize tasks and perform effectively in a fast‑paced environment.
• Excellent verbal and written communication skills.
• Strong analytical and problem‑solving abilities.

• Bachelor’s degree in a related field.
• CompTIA A+, Network+, and/or Microsoft certifications.
• Experience supporting users in an enterprise IT environment.

The anticipated pay range for this position is $55,000–$65,000 annually.

• Flexible Workplace – hybrid and remote options available for many roles.
• Unlimited PTO – competitive paid time off, including flexible & unlimited options.
• Inclusive Environment – a culture that values diversity, collaboration, and respect.
• Growth Opportunities – support for ongoing learning and career development.
• Comprehensive Benefits – health, dental, vision, life, and disability coverage.

We invite applicants to share their demographic background. If you choose to complete this survey, your responses may be used to identify areas of improvement in our hiring process. As set forth in Strongpoint Partners’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.