Territory Account Executive, Restaurant POS

Chowbus; Chicago (IL); On-site; USD 50,000 - 80,000; Full time

Benefits offered by this job

Guaranteed commission draw

Career progression from Territory AE

Hands-on product training

Medical, dental, and vision insurance

401(k) employer-paid

Short-Term Disability (STD) employer-P

Life Insurance

AD&D Insurance

Company holidays

Birthday off

Paid Parental Leave

Flexible PTO

EAP

Fuel reimbursement

Job summary

Chowbus is building a Chicago-based Territory Account Executive to own the full sales cycle with independent and multi-location restaurants. You will meet owners, conduct in-person demos, and close deals that move to onboarding and live operation.

You’ll leverage prior POS/payments experience and a track record of meeting quotas while working in a dynamic, growth-focused environment. Competitive compensation includes salary and commissions.

Qualifications

• 1+ year of quota-carrying, full-cycle B2B sales in hospitality/restaurant tech.
• Experience with restaurant POS or payments (Toast, Square, Clover, SpotOn, Lightspeed).
• Comfortable approaching owners in restaurants; strong English skills.

Responsibilities

• Prospect your territory in person and by phone to own new openings and renewals.
• Run discovery and product demos with owners and general managers.
• Build proposals and model processing rates to close deals.
• Hand off to onboarding and stay involved until live.
• Develop referrals and relationships with local suppliers and partners.
• Maintain updated pipeline in CRM.

Skills

Quota-carrying B2B sales

English proficiency

Self-directed territory management

In-person outreach

Driver's license

Tools

Toast POS

Square POS

Clover POS

SpotOn

Lightspeed

ISO/merchant services

Job description

Chowbus is a leading Asian restaurant technology SaaS platform, with deep roots in the North American market for years. Currently, we stand as a pioneering enterprise in the North American Asian Restaurant SaaS sector. Driven by precise market positioning and efficient product services, our business has achieved doubled growth annually, covering over 30 core states and 100 key cities across the U.S., and partnering with more than 10,000 Asian restaurants. We build tech ecosystems that help restaurants grow, serve with heart, and uplift their communities. Our vision is to create a world where culturally rooted food entrepreneurs thrive everywhere. In 2027 we are launching a new team to bring Chowbus to independent and multi-location restaurants in Chicago, and we are hiring the people who will build that market from day one.

You own a defined territory in Chicago and run the full sales cycle yourself: you find restaurants, meet owners in person, run demos, close, and stay with the account until it is live. Your pipeline is yours.

Many of the restaurants you meet already run Toast, Square or Clover, so a big part of the job is showing owners why switching is worth it and timing the conversation to their contract.

What You'll Focus On

• Prospect your territory in person and by phone: new openings, restaurants on legacy systems, and Toast, Square and Clover customers approaching contract renewal
• Run discovery and product demos with owners and general managers
• Build proposals, model processing rates and total cost against the restaurant’s current system, and close
• Hand off cleanly to onboarding and stay involved until the restaurant is live
• Ask every new customer for referrals and build relationships with local suppliers, associations and partners
• Keep your pipeline and activity up to date in our CRM

What You Bring

• 1+ years of quota-carrying, full-cycle B2B sales; restaurant POS or payments experience (Toast, Square, Clover, SpotOn, Lightspeed, ISO/merchant services) strongly preferred
• A track record of hitting or beating quota, with numbers you can walk us through
• Comfortable walking into restaurants and starting conversations with owners
• Strong spoken and written English; a second language is a plus
• Self-directed and organized enough to run your own territory
• Valid driver’s license and reliable transportation

What We Offer

• Guaranteed commission draw during your first 3 months while you ramp
• A clear path from Territory AE to Senior AE to Sales Manager
• Hands‑on training on the product, the restaurant business and competitive selling
• A fair compensation package
• Medical, dental, and vision insurance
• 401(k) 100% employer-paid
• Short-Term Disability (STD) 100% employer-paid
• Life Insurance and option for additional employee‑paid Life Insurance 100% employer‑paid
• Accidental Death and Dismemberment (AD&D) Insurance and 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

The salary for this role is $50,000-$80,000 plus sales commission, depending on experience.