1

Pos System Jobs in Chicago, IL (NOW HIRING)

Cashier

Matteson, IL

$11.50 - $15.75/hr

This role includes taking orders, handling payments, operating POS system, phone orders and meal preparation. This role also includes ensuring a clean welcoming work environment.

Entry Level Bartender

Romeoville, IL ยท On-site

$9 - $12.18/hr

Enter each order accurately into the POS system. * Uphold the company's core values and ensure optimum guest experience. * Accountable for maintaining quality, consistency, and sanitation standards ...

Automation (POS) Tester

Chicago, IL ยท On-site

$47.50 - $62.50/hr

Experience in eCom, Order Management systems and POS automation is preferred. * Ability to design and build automation framework * Nice to have Mobile automation testing experience using selenium in ...

Showing results 21-40

Pos System information

See Chicago, IL salary details

$44.3K

$112.8K

$171.5K

How much do pos system jobs pay per year?

As of Aug 10, 2026, the average yearly pay for pos system in Chicago, IL is $112,828.00, according to ZipRecruiter salary data. Most workers in this role earn between $87,000.00 and $133,900.00 per year, depending on experience, location, and employer.

What is a POS system?

A point of sale system, often referred to as a POS system, is used by retail businesses to collect payment for purchases of products or services. It includes both software and hardware components. The point of sale system acts as a cash register, determines and displays the purchase amount, and processes payments for both cash and credit card transactions. Some POS systems also track inventory, manage customer loyalty programs, and provide sales reports. There are on-premise systems that are installed on local machines, and cloud-based ones that access information through the internet.

What is the difference between Pos System vs Cashier?

AspectPos SystemCashier
CredentialsBasic technical knowledge, sometimes training on specific POS softwareMinimal formal credentials, customer service skills
Work EnvironmentOperates POS hardware/software, may handle inventory and sales dataHandles transactions at checkout counters, interacts directly with customers
Industry UsageUsed by retail, hospitality, restaurants for sales processingFound in similar settings, primarily as front-line staff

The Pos System refers to the hardware and software used to process sales and manage transactions, often involving inventory and reporting features. A Cashier is a role that involves operating the POS system to complete customer purchases. While cashiers focus on customer interaction and transaction handling, Pos Systems are tools used by cashiers and other staff to facilitate sales. Understanding the difference helps in job descriptions and training programs for retail and hospitality businesses.

What is a POS system?

A POS (Point of Sale) system is a combination of hardware and software that businesses use to process sales transactions. It typically includes a computer or tablet, cash register, barcode scanner, receipt printer, and payment terminal. Modern POS systems also help manage inventory, track sales, and generate reports, making it easier for businesses to operate efficiently. They're commonly used in retail stores, restaurants, and other customer-facing businesses.

What are the key skills and qualifications needed to thrive as a POS system specialist, and why are they important?

To thrive as a POS System Specialist, you need a solid understanding of retail operations, basic IT troubleshooting, and experience with payment processing, often supported by a degree in information technology or related experience. Familiarity with specific POS software (such as Square, Toast, or NCR), network setups, and sometimes certifications like CompTIA A+ are advantageous. Strong problem-solving, customer service orientation, and effective communication skills are crucial for addressing user issues and training staff. These skills ensure smooth transaction processing and minimize downtime, directly impacting business efficiency and customer satisfaction.

What are some common challenges faced by POS system specialists, and how can they successfully overcome them?

POS System Specialists often face challenges such as troubleshooting hardware or software issues under time pressure, adapting to frequent software updates, and ensuring seamless integration with other business systems. To overcome these hurdles, specialists benefit from strong problem-solving skills, staying current with system updates, and developing clear communication channels with both technical teams and non-technical staff. Proactively documenting solutions and best practices can also streamline support and improve response times for future issues.
What are the most commonly searched types of Pos System jobs in Chicago, IL? The most popular types of Pos System jobs in Chicago, IL are:
What job categories do people searching Pos System jobs in Chicago, IL look for? The top searched job categories for Pos System jobs in Chicago, IL are:
Infographic showing various Pos System job openings in Chicago, IL as of August 2026, with employment types broken down into 59% Full Time, and 41% Part Time. Highlights an 98% In-person, and 2% Remote job distribution, with an average salary of $112,828 per year, or $54.2 per hour.

Key Account Customer Success Associate_Chineses Vertical

Chowbus

Chicago, IL โ€ข On-site

$60K - $70K/yr

Full-time

Re-posted 12 days ago


Job description

Chowbus is a leading Asian restaurant technology SaaS platform, with deep roots in the North American market for years. Currently, we stand as a pioneering enterprise in the North American Asian Restaurant SaaS sector. Driven by precise market positioning and efficient product services, our business has achieved doubled growth annually, covering over 30 core states and 100 key cities across the U.S., and partnering with more than 10,000 Asian restaurants. We build tech ecosystems that help restaurants grow, serve with heart, and uplift their communities. Our vision is to create a world where culturally rooted food entrepreneurs thrive everywhere.

The Key Account Customer Success Manager (KACSM) is responsible for building and maintaining long-term relationships with key enterprise clients, ensuring they fully leverage the company's POS solutions to maximize business value. This role supports clients through POS system and feature demonstrations, evaluates solution fit based on operational needs, and guides restaurant locations through onboarding and implementation. The KACSM works cross-functionally with Sales, Product, Technical, and Support teams to deliver a seamless customer experience, drive client satisfaction, and support long-term business success. This is an on-site position in Chicago. Occasional visits to merchant locations and extended hours may be required depending on business needs.

Client Relationship Management
  • Serve as the primary point of contact for master clients, building and maintaining long-term relationships with senior management teams.
  • Gain a deep understanding of clients' business needs and goals, proactively communicating product requirements to internal teams and providing tailored POS solutions to drive client success and satisfaction.
  • Identify upsell and upgrade opportunities within existing accounts to expand product adoption and increase customer value.
  • Recognize expansion opportunities within enterprise restaurant groups and drive new store signings as clients continue to grow.
Product Demos and Implementation
  • Assist large clients in completing POS product demos, ensuring they fully understand system capabilities and solution fit for their operational needs.
  • Support individual store onboarding and go-live processes, ensuring smooth deployment and operational readiness.
Problem Solving and Support
  • Proactively identify and resolve issues related to POS system usage, providing timely support and effective solutions.
  • Coordinate with internal teams to ensure prompt responses to client inquiries and operational challenges.
Client Training and Guidance
  • Deliver comprehensive system training and onboarding guidance to ensure clients are fully proficient in using the POS platform.
  • Conduct regular training sessions and product update meetings to keep clients informed about new features and enhancements.
Cross-Functional Collaboration and Requirement Follow-up
  • Partner closely with Product, Engineering, Technical Support, and Operations teams to ensure client feedback is incorporated into product improvements.
  • Lead regular weekly and monthly client meetings to gather business and product requirements, document feedback, and drive timely follow-up across relevant teams.
What You Bring
  • Advanced Microsoft skills, especially in Excel and Powerpoint required
  • Strong execution skills required
  • Strong problem-solving abilities, with the flexibility to address client needs in fast-paced environments.
  • Self-motivated and capable of leading initiatives independently while contributing to team success.
  • Proficient in data analysis and reporting, and familiar with CRM systems (e.g., Salesforce) and office software.
  • Strong verbal and written communication skills required
  • Bachelor's degree or higher in the related areas preferred
  • 2+ years of experience in customer success management preferred
  • Bilingual proficiency in English and Mandarin required
  • Familiarity with POS systems and business processes within the retail industry preferred

What We Offer

  • A fair compensation package
  • Medical, dental, and vision insurance
  • 401(k)
  • 100% employer-paid Short-Term Disability (STD)
  • 100% employer-paid Life Insurance and option for additional employee-paid Life Insurance
  • 100% employer-paid Accidental Death and Dismemberment (AD&D) Insurance and option for additional employee-paid AD&D Insurance
  • Company holidays
  • Birthday off
  • Paid Parental Leave
  • Flexible Paid Time Off (PTO)
  • Employee Assistance Program (EAP)

The salary for this role is $60000-$70000, plus sales commission, depending on experience.