Chowbus The Senior Territory Account Executive sells full-cycle in Chicago's restaurant market with a path to Sales Manager. The role involves closing deals, coaching new AEs, and eventually leading the city's sales team.
Responsibilities
Ramp (month 1-2): learn the product and the playbook, run your own territory, close your first deal
Produce (month 2-4): reach full productivity and coach 1–2 new AEs on ride-alongs
Lead (month 4-6): run the city’s weekly pipeline meeting, hold 1:1s, own the team’s funnel
Promotion review (end of month 6): personal results, new-hire ramp and team retention
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
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
Qualification
Strong spoken and written EnglishLives in or near ChicagoA fair compensation packageMedical401(k)Company holidaysBirthday offPaid Parental LeaveFlexible Paid Time Off (PTO)Second language
Required
Strong spoken and written English; a second language is a plus
Lives in or near Chicago; valid driver’s license and reliable transportation
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
