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Remote Pos Support Jobs in Chicago, IL (NOW HIRING)

BUYER/PLANNER

Elgin, IL · On-site +1

$75K - $100K/yr

This position is not remote; fully in office. Job Summary: The Buyer/Planner plays a critical role ... Following up on late POs and updating our internal customers. * Resolving backorders and general ...

... Remote Opportunities ROLE OVERVIEW The Preconstruction Manager supports Pivot Energy ... POs, LOIs, EPC agreements, subcontracts, and execution strategy. * Facilitate peer reviews and ...

... Remote Opportunities ROLE OVERVIEW The Preconstruction Manager supports Pivot Energy ... POs, LOIs, EPC agreements, subcontracts, and execution strategy. * Facilitate peer reviews and ...

Preconstruction Manager

Chicago, IL · Remote

$90K - $130K/yr

... Remote Opportunities ROLE OVERVIEW The Preconstruction Manager supports Pivot Energy ... POs, LOIs, EPC agreements, subcontracts, and execution strategy. Facilitate peer reviews and ...

Sales Data Analyst

Chicago, IL · Remote

$105K - $115K/hr

POS velocity, ACV distribution, % promo, share of shelf * Category growth vs. prior year / plan ... Cross-Functional Support (25%) * Lead analytics-driven projects (e.g., new item launch tracking ...

Senior Analyst Inventory Control

Chicago, IL · On-site +1

$78K - $102K/yr

... is a remote position but the ideal candidate should live in the Chicagoland area. " Position ... POs timely in Oracle, ensuring accuracy and appropriate supporting documentation is provided.

Project Intake Manager

Chicago, IL · Remote

$50 - $65/hr

... Support intake and prioritization processes, helping the PMO effectively triage and manage its ... remote position. Application Deadline This position is anticipated to close on Aug 27, 2026. About ...

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Remote Pos Support information

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How much do remote pos support jobs pay per hour?

As of Aug 16, 2026, the average hourly pay for remote pos support in Chicago, IL is $20.16, according to ZipRecruiter salary data. Most workers in this role earn between $16.83 and $21.78 per hour, depending on experience, location, and employer.

What is a Remote POS Support specialist?

A Remote POS (Point of Sale) Support specialist is a professional who provides technical assistance and troubleshooting for POS systems from a remote location. They help retail, restaurant, or service businesses resolve software, hardware, or network issues affecting their sales terminals. Their duties often include guiding users through problem-solving steps, configuring systems, and escalating complex issues as needed. Remote POS Support specialists play a crucial role in minimizing downtime and ensuring smooth sales operations.

What are the key skills and qualifications needed to thrive as a Remote POS Support specialist?

To thrive as a Remote POS Support Specialist, you need strong troubleshooting abilities, familiarity with point-of-sale (POS) systems, and typically a background in IT support or customer service. Experience with remote desktop tools, ticketing systems, and knowledge of specific POS software platforms like Square, Clover, or NCR is often required. Excellent communication, patience, and problem-solving skills help you resolve issues efficiently and maintain positive client relationships. These skills ensure quick and effective support, minimize downtime for businesses, and uphold customer satisfaction in a remote environment.

What is the difference between Remote Pos Support vs Remote Customer Service Representative?

AspectRemote Pos SupportRemote Customer Service Representative
Required CredentialsBasic computer skills, POS system knowledgeCommunication skills, customer service experience
Work EnvironmentRetail or hospitality settings, remote support for POS systemsCall centers, retail, or online support roles
Employer & Industry UsageRetail, hospitality, food serviceVarious industries including retail, telecom, e-commerce
Common Search & ComparisonYesNo

Remote Pos Support focuses on assisting businesses with POS system issues, requiring technical knowledge of POS hardware and software. In contrast, Remote Customer Service Representatives handle general customer inquiries, emphasizing communication and problem-solving skills. While both roles involve remote work, they serve different industry needs and skill sets.

What are some common challenges faced by Remote POS Support specialists, and how can they effectively address them?

Remote POS Support specialists often encounter challenges such as troubleshooting technical issues without physical access to the hardware, communicating clearly with non-technical users, and managing multiple support requests simultaneously. To address these challenges, successful specialists rely on strong problem-solving skills, clear written and verbal communication, and effective use of remote access tools. Building rapport with clients and following structured troubleshooting procedures also help ensure issues are resolved efficiently and professionally.

What are the most commonly searched types of Pos Support jobs in Chicago, IL?

The most popular types of Pos Support jobs in Chicago, IL are:

What job categories do people searching Remote Pos Support jobs in Chicago, IL look for?

The top searched job categories for Remote Pos Support jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Remote Pos Support jobs?

Cities near Chicago, IL with the most Remote Pos Support job openings:

Customer Growth Sales Account Executive

Toast

Geneva, IL • Remote

Full-time

Posted 5 days ago


Job description

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy.

Join Toast's rapidly expanding Customer Growth (Upsell) Sales team! We empower existing SMB Toast POS customers to maximize their success by expanding their product offerings. As a Growth Account Executive, you'll manage a book of existing SMB customers with a goal of driving revenue through expansion and product adoption. This is a full-cycle role where you'll partner with cross-functional teams to deliver value across the Toast platform. Our sales culture is a dynamic blend of competitive drive and collaborative spirit, where winning as a team is paramount.

Note: this is a role where you will be primarily remote, working at home, but also spending occasional time in the field in your assigned territory(s). 

What you'll do (Responsibilities):

As a Customer Growth Account Executive, you will drive revenue growth by:

  • Managing the full sales cycle for customer expansion, identifying and closing upsell opportunities within your assigned territory of existing Toast SMB POS customers, from outbound prospecting to contract negotiation and close.
  • Utilizing consultative selling and discovery, conducting deep discovery to uncover customer pain points and business goals, leveraging consultative sales techniques to position Toast's expanded product offerings.
  • Achieving quota attainment, consistently meeting and exceeding monthly sales revenue and unit booking targets.
  • Executing pipeline management, maintaining a highly organized sales pipeline and activity records within Salesforce CRM and other essential tools.
  • Demonstrating market and product expertise, developing a strong understanding of the competitive landscape to effectively position Toast solutions and articulate their unique value.
  • Engaging in cross-functional collaboration, partnering seamlessly with New Business, Services, and Implementation teams to ensure successful customer onboarding and satisfaction.
  • Applying strategic sales methodology, using proven sales methodologies (ex. Sandler) to uncover urgency, drive value, and create compelling propositions.

What you'll need to thrive (Requirements):

We're looking for a driven and adaptable sales professional with:

  • Proven sales acumen, including 2+ years of quota-carrying sales experience in a closing role (ex. Business Development Representative, Account Executive), with a consistent track record of meeting and exceeding monthly sales performance goals.
  • A track record of success in a high-velocity or high-volume, transactional B2B SaaS sales environment.
  • Expertise in full-cycle sales skills, including deep discovery, compelling storytelling, persuasive negotiation, and effective closing techniques.
  • A consultative approach, with the ability to act as a strategic consultant, challenging prospects' perspectives and driving new ways of thinking about their business.
  • A growth and ownership mindset, being highly self-motivated, competitive, resilient, and taking strong ownership of results.
  • Exceptional communication skills, including excellent written and verbal communication, coupled with strong time management and organizational abilities.
  • The ability to adapt, with a proven capacity to thrive and adjust in a dynamic, rapidly evolving sales environment.

What will help you stand out (Nonessential Skills/Nice to Haves):

  • Familiarity with Salesforce CRM.
  • Experience with Sandler Sales Training or similar structured sales methodologies.
  • Prior B2B sales experience within the SMB, restaurant, hospitality, or retail sectors.

AI at Toast

At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it's a core part of our culture.

Our Total Rewards Philosophy 
We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters' changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.