Territory Sales Manager Jobs in Chicago, IL
Territory Sales Manager jobs in Chicago are in strong demand, concentrated in the Loop, River North, and the Fulton Market district, across medical devices, industrial distribution, and technology. Johnstone Supply, XDS, and ZimVie are among the employers posting openings right now. See the openings below and apply to the ones that match your experience.
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Creative Outdoor Advertising, a leader in outdoor signage for over 40 years, is looking for 2 extremely motivated and results-driven full-time Territory Sales Representatives in Chicago, Illinois to sell street furniture advertising space on benches to local businesses. Don’t miss out on this once-in-a-lifetime opportunity to be part of a groundbreaking sales team in this exclusive Midwest market!
Compensation & Schedule
Our pay structure is competitive, and performance driven. We offer a minimum guaranteed salary of $50,000 for the first 12 months while getting established in the role, with the built-in incentive to earn more with commissions. A successful sales rep will bring in long-term earnings of $100,000+ and there is the opportunity for continued growth. This position works predominantly remotely from your home office alongside fieldwork in your local territory. The schedule is Monday – Friday 8:30 am to 5:00 pm.
Position Overview
Based out of your home office, the role is to find local advertising clients through networking and cold calling (in person, phone calls, and email). Focusing on small businesses like dentists, restaurants, real estate agents, lawyers, attorneys, etc. At $153 per month for a 1-year agreement (including artwork) our signs are among the most cost-effective ways for local businesses to communicate their message with potential customers.
What will set you apart?
Being confident and comfortable with cold-calling and approaching local businesses. This is how you will generate most of your sales!
Territory
The are vacancies in Santa Clara for two savvy sales professionals to hit the ground running. Ideally you live in one of these areas in Santa Clara, have knowledge of the local businesses:
- Chicago Central Area: The territory is throughout downtown/central Chicago. With units located from the Navy Pier through to the Berkely/interstate 280 area, the top boarder is W. Division St., up Cicero Ave., then along W. Grande Ave., and the bottom border is W. 31st St.
- Chicago South Area: The territory is throughout southern Chicago. With the majority of the units between the waterfront, 95th St., and interstate 55. There are some units scattered throughout Sauk Village, Frankfort, Joliet, Downes Grove, Crest Hill, and Homer Glen.
Please indicate which territory you live in & are interested in when applying.
Our ideal candidate:
- Lives in Chicago in one of the areas mentioned above, with access to all the advertising benches and shelters in the territory
- Ability to learn new software like Salesforce, our internal database, navigating Google Maps, and other internet-based tools
- Extremely self-motivated, a self-starter who enjoys prospecting and pushing to meet targets and achieve sales wins
- Willingness to use our low-key, low-pressure sales approach, and follow our proven sales techniques
- Outstanding communication skills (verbal and written) and interpersonal skills
- Well organized, charismatic, self-motivated, and hard-working
- Valid Driver’s License and ownership of an insured vehicle
- Someone who is looking for a career - not just a job
- Advanced computer and technology skills
- Easily coachable and enjoys learning
We provide:
- Comprehensive introductory training, including health and safety training, and ongoing support to provide the knowledge and tools to succeed – like our Sign U Sales Training and office equipment
- Eligibility for flexible ICHRA medical benefits after 3 months, with options for dental, vision, life, and disability insurance
- Convenient pay that is direct deposited to your bank account bi-weekly on Fridays
- The flexibility to work out of your home and manage your schedule and calendar
- After 1 year of employment, eligibility in our profit-sharing program
- Attractive earnings, sales contests, and advancement opportunities
- A company-provided work cell phone
- 2 weeks of paid vacation per year
Creative Outdoor accepts applications from all career backgrounds—while account management and sales experience are helpful, your personal dedication and drive to succeed are what matter most. We welcome and encourage applications from people with disabilities; accommodations are available on request for candidates taking part in all aspects of the selection process. This posting is for an existing vacancy, and artificial intelligence tools are not used to screen, assess, or select applicants for this position.
Visit us at www.CreativeOutdoor.com to learn more about our dynamic, growing company.
“Remember, a business without a sign is a sign of no business”
Pay: From $100,000.00 per year
Benefits:
- Cell phone reimbursement
- Dental insurance
- Health insurance
- Life insurance
- Paid time off
- Paid training
- Vision insurance
- Work from home
Application Question(s):
- Do you have a valid driver's license?
- Can you drive throughout the territory in Chicago as needed for in person meetings, door knocking, canvassing, and other sales initiatives?
Experience:
- B2B sales: 1 year (Required)
Work Location: On the road
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Territory Sales Manager Jobs in Chicago: Frequently Asked Questions
How do I get a territory sales manager job in Chicago?
Focus your search on Chicago's strongest hiring sectors: medical devices and pharma along the North Shore corridor, industrial and building materials distributors on the city's Southwest Side, and B2B technology firms concentrated in the Loop and River North. Employers here favor candidates with demonstrated Chicago-market relationships and a book of business in the region. Tailoring your resume to show Midwest territory ownership, not just quota attainment, gives you a clear edge with local hiring managers.
Which companies hire territory sales managers in Chicago?
Chicago territory sales manager roles are posted by Johnstone Supply, XDS, and ZimVie and others right now, based on current listings on Migrate Mate as of November 2026. Chicago's hiring mix skews toward large regional distributors, Fortune 500 manufacturers with Midwest headquarters, and fast-growing healthcare and medtech companies with national field sales operations based in the city.
Are there remote territory sales manager jobs in Chicago?
Yes, though territory sales manager work is inherently field-based, so fully remote roles are less common than in purely desk-bound functions. About 100% of territory sales manager openings tied to Chicago are remote or hybrid as of November 2026, reflecting roles where account management, pipeline reporting, and customer calls can be handled off-site. The in-person requirement typically covers client visits across the assigned Midwest or Great Lakes territory.
How can I get a territory sales manager job in Chicago with little or no experience?
The most realistic entry path in Chicago is moving up from a sales development representative or inside sales role at a Loop or River North B2B technology company, where promotion to territory ownership happens faster than at legacy manufacturers. Chicago-area medical device companies also run structured associate rep programs that place early-career candidates alongside senior reps covering the Illinois and Indiana market. Building familiarity with the Chicago commercial real estate, healthcare, or logistics ecosystem before applying strengthens your candidacy noticeably.
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