Territory Account Executive, Restaurant POS (Full-Cycle)-Chicago

Chowbus • Chicago, IL

6d

About The Position

Chowbus is hiring a Territory Account Executive to help launch its restaurant technology business with independent and multi-location restaurants in Chicago in 2027. The role owns a defined territory and manages the full sales cycle, from prospecting and in-person meetings through product demonstrations, closing, and remaining involved until each restaurant is live. The position includes engaging restaurants using legacy systems or competing products such as Toast, Square, and Clover, and helping owners assess the value and timing of switching systems. Compensation is $50,000–$80,000 plus sales commission, depending on experience.

Requirements

• At least 1 year of quota-carrying, full-cycle B2B sales experience.
• A track record of meeting or exceeding quota, with results the candidate can explain.
• Comfort walking into restaurants and starting conversations with owners.
• Strong spoken and written English.
• Self-directed and organized enough to manage an assigned territory.
• Valid driver’s license and reliable transportation.

Nice To Haves

• Restaurant POS or payments experience, including experience with Toast, Square, Clover, SpotOn, Lightspeed, ISO, or merchant services.
• Ability to speak a second language.

Responsibilities

• Prospect the assigned territory in person and by phone, focusing on new openings, restaurants using legacy systems, and customers of Toast, Square, and Clover approaching contract renewal.
• Conduct discovery and product demonstrations with restaurant owners and general managers.
• Prepare proposals, model processing rates and total costs against restaurants’ current systems, and close sales.
• Coordinate handoffs to onboarding and remain involved until the restaurant is live.
• Ask new customers for referrals and build relationships with local suppliers, associations, and partners.
• Keep pipeline and activity information up to date in the CRM.

Benefits

• Guaranteed commission draw during the first 3 months while ramping.
• Hands-on training on the product, restaurant business, and competitive selling.
• Medical insurance.
• Dental insurance.
• Vision insurance.
• 401(k) with 100% employer-paid contribution, as stated in the posting.
• 100% employer-paid Short-Term Disability insurance.
• 100% employer-paid Life Insurance, with an option for additional employee-paid coverage.
• 100% employer-paid Accidental Death and Dismemberment insurance, with an option for additional employee-paid coverage.
• Company holidays.
• Birthday off.
• Paid Parental Leave.
• Flexible Paid Time Off (PTO).
• Employee Assistance Program (EAP).
• Fuel reimbursement.
• Clear career path from Territory AE to Senior AE to Sales Manager.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed