IT Helpdesk II Chicago, IL

SpotOn, Inc.; Chicago, Northern (IL, KY); Hybrid; USD 45,000 - 65,000; Full time

Job summary

SpotOn, Inc. in Chicago is seeking an Helpdesk Technician to support a broad range of IT tasks for employees and contractors. You will handle user administration, device support, licensing, and onboarding/offboarding, while providing frontline and escalation support for IT incidents.

The role focuses on regular office IT duties, asset tracking, and participation in special IT projects, ensuring confidentiality and smooth operations for a growing company.

Qualifications

• Intermediate experience with user administration and onsite IT support.
• Experience with desktop hardware/software troubleshooting and asset management.
• Familiarity with licensing provisioning/deprovisioning and onboarding/offboarding processes.

Responsibilities

• Handle tickets for user administration, device issues, licensing, and onboarding/offboarding.
• Provide desktop hardware/software support and patching in a fast-paced environment.
• Manage licensing provisioning and deprovisioning for employees and contractors.
• Respond to VIP/ELT issues and escalate as needed.
• Track assets and perform regular audits of accounts and access.
• Lead special IT projects and office tasks as assigned.

Skills

Okta admin

Google Workspace admin

Mac/Windows configuration

Desktop troubleshooting

PC hardware repair

Networking basics

VoIP/telephony

English communication

Education

High school diploma

CompTIA A+/Network+ or similar

Tools

Okta

Google Workspace

MacOS

Windows

VoIP systems

Job description

About SpotOn

We’re not just building restaurant tech, we’re giving independent restaurants the tools to compete and win. From our award-winning point-of-sale to AI-powered profit tools, everything we do helps operators boost profit, work smarter, and keep their best people. And every solution is backed by real humans who actually give a sh*t about helping restaurants succeed.

• Named the #1 Restaurant POS by G2 (Summer 2026), based on ratings from real users

• Rated the top-rated point-of-sale (POS) for restaurants, bars, retail, and small businesses by Capterra users

• Awarded Great Places to Work and Built In’s Best Workplaces for multiple years running

We move fast, care hard, and fight for independent restaurant operators to do what they love, and love doing it. If you’re looking to make an impact with heart and hustle, SpotOn is the place for you.

Helpdesk Technicians support Spot On Employees and Contractors requiring attention to confidentiality. This is a generalist role involving a broad range of tasks. Level II Technicians focus on tickets for the majority of their day – both frontline and as an initial escalation point of contact. Helpdesk also works on recurring tasks and special projects, including handling a wide range of responsibilities within the office to which they are assigned.

ESSENTIAL FUNCTIONS

• Keep regular office hours in assigned SpotOn office

• Handling tickets for tasks such;

  • User administration (onboarding, offboarding, changes, resets, unlocks, etc)

  • Desktop support (hardware, software, and services)

  • Licensing (provisioning and deprovisioning)

  • Hardware requests

• First response for issues from VIP (ELT & EAs)

• Asset tracking (assignment, return, retirement)

• Auditing (User and Accounts)

• Regular maintenance and patching

• Specialist for specific products and services

• Takes ownership of special projects as needed

• Respond to unexpected issues

• Other duties and projects as assigned

MINIMUM QUALIFICATIONS

• Intermediate Knowledge of Okta User/Group Management

• Intermediate Knowledge of Google Workspace User/Group Management/Administration

• Intermediate Knowledge of Macintosh and Windows Configuration and Administration

• Moderate Skill in Troubleshooting Desktop Hardware

• Basic Skill in Upgrading and basic repair of PC hardware

• Moderate Knowledge with Networking Technologies

• Moderate Knowledge in VoIP Softphone and Telephony Services

• Good US English verbal and written communication skills (multi-lingual preferred)

EXPERIENCE REQUIREMENTS

• 3 year in similar Helpdesk role

• 2 years with Google Apps for Business or similar service

• 2 years with Okta or similar service

EDUCATION REQUIREMENTS

• High school diploma

• CompTIA A+, Network+, and/or Tech+ or similar preferred

PHYSICAL AND MENTAL REQUIREMENTS AND WORKING CONDITIONS

• Must be able to remain in a stationary position a minimum of 50% of the work day

• The person in this position needs to occasionally move about inside the office to access file cabinets, office machinery, etc.

• Occasionally lifts and carries equipment in the office weighing up to 20 pounds

We will never ask candidates to pay fees, purchase equipment, or share sensitive personal or financial information during the hiring process. All legitimate communication from our recruiting team will come from an official company email address (@spoton.com). If something seems suspicious, please contact us at [e-mail].

SpotOn is an equal employment opportunity employer. Qualified candidates are considered for employment without regard to race, religion, gender, gender identity, sexual orientation, national origin, age, military or veteran status, disability, or any other characteristic protected by applicable law.

For U.S. based roles, work authorization in the U.S. is required. Visa sponsorship is not available for this role.

SpotOn is an E-Verify company.