IT Helpdesk II

SpotOn; Chicago (IL); On-site; USD 50,000 - 68,000; Full time

Job summary

SpotOn in Chicago seeks a Helpdesk Technician to support employees and contractors, focusing on confidentiality, frontline and escalation tasks. The role requires handling user administration, desktop support, licensing, and hardware requests, with ownership of asset tracking and regular maintenance.

You will respond to VIP requests, assist with special projects, and ensure timely resolution of issues, using Okta, Google Workspace, Windows and Macintosh environments.

Qualifications

• Evidence of experience providing IT helpdesk support and frontline escalation.
• Experience with user administration (onboarding, offboarding, changes, resets).
• Familiarity with licensing, hardware requests, and asset tracking.

Responsibilities

• Keep regular office hours at SpotOn office in Chicago.
• Handle tickets including user administration, desktop support, licensing, and hardware requests.
• First response for issues from VIP staff; manage asset tracking and audits.
• Maintain and patch systems; take ownership of special projects as needed.
• Respond to unexpected issues and other duties as assigned.

Skills

Customer service

Communication

Confidentiality

Office procedures

Education

High school diploma

CompTIA A+ / Network+ / Tech+

Tools

Okta

Google Workspace

Macintosh & Windows Config

VoIP Telephony

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 SpotOn 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 as;

  • 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.

Work authorization in the U.S. is required. Visa sponsorship is not available for this role.

SpotOn is an E-Verify company.