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Territory Sales Representative/ Restaurant Specialist - Chicago, IL

SpotOn - Chicago, IL, USA - Hybrid - posted 2026-09-22

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Salary: USD 60,000 - 275,000 / annual

SpotOn is a restaurant technology company offering award-winning point-of-sale (POS) systems and AI-powered profit tools for independent restaurants. The company is named the #1 Restaurant POS by G2 and is a multiple-time Great Places to Work honoree. In this Territory Sales Representative role, you will be the local SpotOn representative in Chicago, responsible for building relationships with restaurant owners and small business operators in your assigned territory. You will manage the complete sales cycle from prospecting through closing, with a focus on selling POS software solutions and payment processing services. Key responsibilities include traveling to client sites within your territory to prospect and sign new merchants, managing a growing portfolio of clients, hitting monthly sales targets in collaboration with the sales support team, and maintaining strong client relationships to ensure customer success and satisfaction. This is a full-time, W2 hybrid position based in Chicago. You will work in your local territory with flexibility to manage your schedule while meeting sales performance goals. Qualifications: - 2+ years of B2B sales experience with emphasis on small business owners, merchants, and restaurants - Proven track record delivering against sales goals with a metrics-oriented, competitive mindset - Excellent cold calling, prospecting, and territory buildout experience - Proficiency in Salesforce CRM (preferred) - Ability to learn technology basics and apply them to business situations - Strong client relationship management skills in collaboration with internal support teams - Ability to embrace feedback and hold yourself accountable

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