Senior Territory Account Executive – Manager Track – 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.

This is a selling role with a defined path to management. You start as a Senior Territory AE, prove the market in Chicago by closing deals yourself, then take over as Sales Manager for the city. With prior team-lead experience, the path to Manager is 3 months; otherwise it is 6 months. The promotion criteria are written into your offer.

1. Ramp (month 1-2): learn the product and the playbook, run your own territory, close your first deal
2. Produce (month 2-4): reach full productivity and coach 1–2 new AEs on ride-alongs
3. Lead (month 4-6): run the city’s weekly pipeline meeting, hold 1:1s, own the team’s funnel
4. Promotion review (end of month 6): personal results, new-hire ramp and team retention

What You'll Focus On

• Sell full-cycle in your own territory: prospect, demo, close and see each restaurant through to go-live
• Win restaurants away from Toast, Square and Clover by timing the conversation to their contract and showing the full cost comparison
• Help interview and onboard the next AEs in Chicago, and coach them through their first deals
• Map the city: which neighborhoods to open first, which partners and associations to work with
• After promotion, lead a team of AEs while keeping a personal quota

What You Bring

• 3+ years of quota-carrying B2B sales, with restaurant POS or payments experience (Toast, Square, Clover, SpotOn, ISO/merchant services) strongly preferred
• Experience leading, mentoring or onboarding salespeople: a team lead, sales manager or senior rep who trained others
• Consistent quota attainment you can show with numbers
• Comfortable building a market from zero: walking into restaurants, setting up partnerships, figuring things out without a playbook handed to you
• Strong spoken and written English; a second language is a plus
• Lives in or near Chicago; valid driver’s license and reliable transportation

What We Offer

• 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.