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Territory Sales Representative/ Restaurant Specialist - Chicago, IL

SpotOn - Chicago, IL, United States - Hybrid - posted 2026-07-27

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

SpotOn is a restaurant technology company offering point-of-sale systems, payment processing, and AI-powered profit tools to independent restaurants and small businesses. The company is ranked #1 Restaurant POS by G2 and Capterra, and has been recognized as a Great Place to Work. In this Territory Sales Representative role, you will be the local SpotOn representative in Chicago, responsible for prospecting, building relationships, and closing deals with restaurant owners and small business operators in your assigned territory. You will manage the complete sales cycle from initial outreach through contract signature, with a focus on selling the full product suite including POS systems and payment processing solutions. Key responsibilities include: - Conducting local territory development through cold calling, prospecting, and relationship building with restaurant owners and merchants - Traveling to client sites to demonstrate products and understand business needs - Managing a growing portfolio of accounts and maintaining client relationships post-sale - Hitting monthly and quarterly sales targets with accountability for revenue generation - Collaborating with the Sales Support team to ensure customer success and retention - Learning and applying technology fundamentals to business conversations You should have 2+ years of B2B sales experience, ideally with small business owners or restaurants. A proven track record of hitting sales goals, strong prospecting skills, and comfort with Salesforce CRM are important. The ideal candidate is metrics-driven, coachable, and has an entrepreneurial mindset. Compensation includes a $60,000 base salary with total on-target earnings of $120,000–$275,000 including commission, bonuses for hardware/implementation, monthly production bonuses, and retention incentives. The package also includes medical/dental/vision, 401(k) match, RSUs, paid time off, parental leave, education reimbursement, and commuter benefits.

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