Outside Sales Representative Jobs in Chicago, IL
Outside sales representatives in Chicago work a territory by car, and posted pay runs from about $47,000 base at Sysco to $150,000 with commission and a car allowance at Cintas. Here are the current openings, followed by who is hiring, which territories they cover and how the pay is built.
Current outside sales representative Openings in Chicago, IL
Listings marked External are sponsored openings provided by the Jobs2Careers network.
Outside Sales Representative Work in Chicago
Most Chicago outside sales jobs are built around suburban branches and a slice of the map. Cintas assigns uniform and facility services territories out of Maywood, Romeoville, Schaumburg and Gurnee. Sysco Chicago sends reps to restaurant kitchens across Des Plaines, Evanston and Skokie. Grainger's Imperial Supplies unit covers the Chicago automotive market, and Comcast Business works small businesses out of its office on W. North Avenue.
That means real driving. A territory can run up the Edens to the North Shore, out the Eisenhower to the west suburbs or down the Stevenson toward Romeoville, and winter adds time to every call. Employers plan for it: Cintas pays a monthly car allowance plus insurance, gas and maintenance, and Sysco requires reps to carry set auto insurance limits on their own vehicle.
Top Chicago Employers Hiring Outside Sales Representatives
These employers had outside or territory sales openings in the Chicago area on their own careers sites this month:
- Cintas - hires facility services and uniform sales reps in Maywood, Romeoville and Schaumburg at an estimated $60,000 to $150,000 with commission, bonus and car allowance.
- Sysco - Sysco Chicago hires sales reps for restaurant accounts in Des Plaines, Evanston and Skokie at $47,200 to $78,600.
- Grainger - its Imperial Supplies unit hires a district sales rep for the Chicago automotive market at $70,000 base plus a $20,000 first-year bonus guarantee.
- ADP - hires account executives out of 233 S. Wacker Drive to sell payroll and HR services in a protected territory at $50,100 to $99,800 base.
- Comcast Business - hires field account executives for Chicago small businesses at $68,750 base and $118,750 target, and door-to-door Xfinity reps in Schaumburg, Romeoville and Homewood.
Outside Sales Representative Salaries in Chicago
- Entry level: about $47,000 to $60,000 base, plus commission and often a car allowance.
- Experienced: roughly $60,000 to $120,000 a year with commission.
- Senior: $120,000 to $150,000 or more for strong territories and technical products.
These are estimates built from BLS May 2025 wage data for Chicago metro sales representatives, where the 75th percentile is about $101,600, and from ranges Chicago employers posted this year. Outside pay moves with the commission plan, the territory and the product: a first-year guarantee like Imperial's protects you while you build accounts, and the car allowance at Cintas is worth counting when you compare offers.
How to Become an Outside Sales Representative in Chicago
Illinois does not license outside sales reps, though insurance sellers need a producer license from the Illinois Department of Insurance. What you do need is a valid driver's license and a clean record, since Cintas and Sysco both require one. Cintas and Sysco accept a high school diploma or GED with experience, while ADP asks for a degree or three years of B2B sales. DePaul University's Center for Sales Leadership in the Loop offers a sales leadership minor, and City Colleges of Chicago offers a Business Apprenticeship associate degree at Harold Washington, Truman, Daley and three other campuses.
What the Job Involves
Outside sales reps build their own pipeline inside a territory. That means cold calling and walking in on businesses, running product demos on site, writing proposals, negotiating price and closing, then checking in with accounts so they renew. Reps plan routes, log activity in a CRM from the car and hit weekly targets for appointments and new business.
Skills Employers Look For
- A valid driver's license and a clean driving record
- Comfort with cold calls and walk-ins
- In-person presenting and product demos
- Negotiating and closing
- Planning a territory and your own schedule
- CRM and Microsoft Office basics
- A second language, which Sysco and Comcast list as a plus
Career Path and Advancement
Many Chicago outside reps start in inside sales or route service, such as the assistant route service sales roles Cintas runs out of Bedford Park and Schaumburg, then take a territory. Strong reps move to larger territories or major accounts, as ADP's Major Accounts team shows, and on to sales manager. Cintas also hires management trainees across Chicagoland.
Related Careers in Chicago
If outside sales interests you, these related Chicago roles are close matches:
Frequently Asked Questions
Do outside sales jobs in Chicago give you a car?
Some pay for yours instead. Cintas pays a monthly car allowance with insurance, gas and maintenance, while Sysco asks reps to drive their own vehicle with set insurance limits. Ask how mileage is handled before you accept.
How much do outside sales reps make in Chicago?
Posted Chicago ranges run from $47,200 to $78,600 at Sysco to an estimated $60,000 to $150,000 at Cintas. Comcast Business posts $68,750 base with a $118,750 target for experienced reps.
Do you need a license for outside sales in Illinois?
No, not for general outside sales. The exception is insurance, where the Illinois Department of Insurance requires a producer license before you can sell.
Can you get an outside sales job without a degree in Chicago?
Yes. Cintas and Sysco accept a high school diploma or GED, with Sysco asking for three years of relevant experience in that case. Comcast's door-to-door Xfinity roles also start at a high school diploma.
What is the difference between inside and outside sales?
Inside reps sell by phone and video from an office or home. Outside reps meet customers in person across a territory, drive most days and often get a car allowance or mileage pay.
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