Senior Territory Account Executive – Manager Track – Chicago

Chowbus•Chicago, IL

6d•$50,000 - $80,000

About The Position

Chowbus is hiring a Senior Territory Account Executive to help launch its Chicago market in 2027, selling its restaurant technology SaaS platform to independent and multi-location restaurants. This is a selling role with a defined path to Sales Manager: the hire first proves the market by closing deals personally, then takes over sales management for the city. Candidates with prior team-lead experience may follow a three-month path to Manager; otherwise, the path is six months. Promotion criteria are written into the offer. The six-month standard track includes ramping up on the product and playbook, managing a territory, and closing a first deal during months one and two; reaching full productivity and coaching one or two new AEs during months two through four; and leading weekly pipeline meetings, conducting one-to-ones, and owning the team funnel during months four through six. The promotion review at the end of month six considers personal results, new-hire ramp, and team retention. The role involves full-cycle selling in an assigned territory, including prospecting, demonstrations, closing, and supporting each restaurant through go-live. The hire will compete with providers such as Toast, Square, and Clover, help build the Chicago market, and, after promotion, lead a team of AEs while maintaining a personal quota. The position is based in or near Chicago and requires a valid driver’s license and reliable transportation.

Requirements

At least 3 years of quota-carrying B2B sales experience.
Experience leading, mentoring, or onboarding salespeople, such as as a team lead, sales manager, or senior representative who trained others.
Consistent quota attainment that can be demonstrated with numbers.
Comfort building a market from zero, including walking into restaurants, setting up partnerships, and working without a provided playbook.
Strong spoken and written English.
Live in or near Chicago.
Have a valid driver’s license and reliable transportation.

Nice To Haves

Restaurant POS or payments experience, including experience with Toast, Square, Clover, SpotOn, ISO, or merchant services, is strongly preferred.
A second language is a plus.

Responsibilities

Prospect, demonstrate, and close deals in an assigned territory, and see each restaurant through to go-live.
Win restaurants from Toast, Square, Clover, and other competitors by timing conversations around contract dates and presenting a full cost comparison.
Help interview and onboard new Chicago AEs, and coach them through their first deals.
Map Chicago neighborhoods to determine where to open first and identify partners and associations to work with.
After promotion, lead a team of AEs while maintaining a personal quota.
During the management-track progression, coach one or two new AEs, run the city’s weekly pipeline meeting, hold one-to-ones, and own the team funnel.

Benefits

Medical, dental, and vision insurance.
401(k).
100% employer-paid Short-Term Disability insurance.
100% employer-paid Life Insurance, with the option to purchase additional employee-paid Life Insurance.
100% employer-paid Accidental Death and Dismemberment insurance, with the option to purchase 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.
Sales commission.