Senior Territory Account Executive – Manager Track – Chicago

Chowbus•Chicago, IL

About The Position

Chowbus is hiring a Senior Territory Account Executive to help launch its business with independent and multi-location restaurants in Chicago. This is a full-cycle selling role with a defined path to Sales Manager. The employee will initially build and manage their own territory, close deals, and help establish Chowbus’s presence in the Chicago market. Candidates with prior team-lead experience may follow a three-month path to Manager; otherwise, the path is six months, with promotion criteria written into the offer. The stated six-month progression is: Ramp (months 1–2), learning the product and playbook, running a territory, and closing a first deal; Produce (months 2–4), reaching full productivity and coaching one or two new Account Executives on ride-alongs; Lead (months 4–6), running the city’s weekly pipeline meeting, holding one-on-ones, and owning the team funnel; and a promotion review at the end of month 6 based on personal results, new-hire ramp, and team retention. The standard track follows the same steps over six months. After promotion, the employee will lead a team of Account Executives while maintaining a personal quota. The salary range is $50,000–$80,000, depending on experience, plus sales commission.

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 has trained others.
Demonstrated consistent quota attainment, supported by numbers.
Comfort building a market from zero, including walking into restaurants, establishing partnerships, and working without a pre-existing playbook.
Strong spoken and written English.
Live in or near Chicago.
Valid driver’s license and reliable transportation.

Nice To Haves

Restaurant POS or payments experience, including experience with Toast, Square, Clover, SpotOn, or ISO/merchant services.
A second language.

Responsibilities

Manage a territory through the full sales cycle: prospect, demonstrate the product, close deals, and support each restaurant through go-live.
Win restaurants from Toast, Square, and Clover by timing conversations around their contracts and presenting a full cost comparison.
Help interview and onboard new Account Executives in Chicago and coach them through their first deals.
Map the Chicago market, including neighborhoods to open first and partners or associations to work with.
After promotion, lead a team of Account Executives while maintaining a personal quota.
As part of the management progression, run the city’s weekly pipeline meeting, hold one-on-ones, and own the team funnel.

Benefits

Medical, dental, and vision insurance.
401(k) with 100% employer-paid contributions, as stated in the posting.
100% employer-paid Short-Term Disability insurance.
100% employer-paid Life Insurance, with an option for additional employee-paid Life Insurance.
100% employer-paid Accidental Death and Dismemberment insurance, with an option for additional employee-paid coverage.
Company holidays.
Birthday off.
Paid parental leave.
Flexible Paid Time Off (PTO).
Employee Assistance Program (EAP).
Fuel reimbursement.
Sales commission.