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

Chowbus • Chicago, IL

6d • $50,000 - $80,000

About The Position

Chowbus is hiring a Territory Account Executive to help launch its Chicago sales team in 2027 and bring its restaurant technology platform to independent and multi-location restaurants. The role owns a defined Chicago territory and manages the full sales cycle, from prospecting and in-person meetings through demonstrations, proposals, closing, and follow-through until each restaurant is live.

The role focuses in part on restaurants using legacy systems or Toast, Square, and Clover, including customers approaching contract renewal. The Account Executive will explain the value of switching, model processing rates and total costs against a restaurant’s current system, and build local relationships to generate referrals and business. The position offers a guaranteed commission draw for the first three months while ramping, product and sales training, and a stated progression path to Senior AE and Sales Manager.

Requirements

• At least 1 year of quota-carrying, full-cycle B2B sales experience.
• A record of meeting or exceeding quota, with results the candidate can explain.
• Comfort with walking into restaurants and initiating conversations with owners.
• Strong spoken and written English.
• Self-direction and organization sufficient to manage an individual 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 Chicago territory in person and by phone, targeting new openings, restaurants using legacy systems, and Toast, Square, and Clover customers approaching contract renewal.
• Conduct discovery conversations 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 each restaurant is live.
• Request referrals from new customers and develop relationships with local suppliers, associations, and partners.
• Keep pipeline and sales activity 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, dental, and vision insurance.
• 401(k).
• 100% employer-paid Short-Term Disability (STD).
• 100% employer-paid Life Insurance, with an option for additional employee-paid Life Insurance.
• 100% employer-paid Accidental Death and Dismemberment (AD&D) Insurance, with an option for additional employee-paid AD&D Insurance.
• Company holidays.
• Birthday off.
• Paid Parental Leave.
• Flexible Paid Time Off (PTO).
• Employee Assistance Program (EAP).
• Fuel reimbursement.
• Fair compensation package.
• Clear path from Territory AE to Senior AE to Sales Manager.

What This Job Offers

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