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

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.