Sales Representative Jobs in Chicago, IL
Sales Representative jobs in Chicago are in strong demand, concentrated in the Loop, River North, and Fulton Market across technology, healthcare, and financial services. Employers actively hiring include Uber, Braze, and Rippling. See the openings below and apply to the ones that match your experience.
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Your Title: Territory Sales Representative
Your Location: Territory based position covering Chicago and the surrounding areas.
You Report To: Regional Sales Manager
Learn more about our awesome Sales team!
About the Opportunity:
First Help Financial, voted and certified as a “Great Place to Work” by our workforce for five years in a row, is adding a new partner to our Outside Sales department to accommodate our remarkable growth!
As a Territory Sales Representative, you'll be at the forefront of our business, managing loan originations and cultivating strong relationships with auto dealerships across Illinois. This isn't just another desk job—you'll be out in the field, meeting clients, and making an impact. If you do not aspire to the typical 9-5 job but enjoy meeting and dining with business clients 40+ hours a week then this is an opportunity for YOU. This opportunity reimburses you for your extensive car travel within your designated geography.
Compensation & Career Growth:
- A starting base salary of $70,675 or more plus a quarterly performance bonus, depending upon experience.
- First quarter bonus is guaranteed while you are training.
- Robust sales training program, ongoing career development opportunities, and a vibrant work culture, you'll have everything you need to succeed and grow with us.
Benefits:
- Competitive health and welfare benefits starting DAY ONE!
- Monthly mileage reimbursement.
- Paid vacation, sick time, and holiday pay.
- 401(k) match.
- Tuition reimbursement, quarterly social outings, monthly lunches, a robust employee recognition program, and a training development program to enhance your career with us.
What you will do:
- Build and maintain strong relationships with current and prospective auto dealerships in your territory.
- Serve as the primary point of contact for dealership accounts, requiring availability via phone, text, or email during the business hours of accounts in this territory.
- Educate dealerships on our services.
- Prospect auto dealerships for future business, including cold-calling.
- Weekly travel to dealerships in your designated geography.
What you Bring:
- Minimum of 3+ years of relevant sales or business development experience (auto financing, banking, or dealership experience is a plus).
- Valid US Drivers License.
- Reliable Transportation.
- Demonstrates historical career stability.
- CRM experience.
- High level of independence; detail-conscious and task-oriented mindset.
- Excellent consultative selling skills.
- Prospecting, planning, presenting and closing skills.
- Initiative, sense of urgency and passion for winning.
- Strong interpersonal and teamwork skills.
- Ability to develop and maintain effective relationships, including cold calling.
- Strong problem-solving skills and capacity to manage difficult relationship situations.
- Excellent written and verbal communication skills.
- Strong computer skills (knowledge of Microsoft Excel, PowerPoint, and Word).
- Bachelor's degree preferred or equivalent work experience.
About us:
First Help Financial (FHF) is a fast-growing and culturally diverse company in the U.S. We provide auto loans to the underserved and care for our customers and partners with exceptional service. Through flexible financing options and tri-lingual support, we offer consumers an easier way to finance their first car. We lend to and support our portfolio which has consistently grown 30%+ each year over the last nine years.
Here you will find hard-working colleagues who come from over 20 countries. We hold ourselves to the highest standards of professionalism but also enjoy our work. Our culture and benefits are geared towards making you successful in life and comfortable at work.
FHF Benefits:
- Great Perks – We offer generous salaries, competitive health and welfare benefits (medical, dental, vision, LTD/STD, Identity theft, paid parental leave and much more), paid vacation, 401(k) match, tuition reimbursement, social activities, monthly lunches, a robust employee recognition and talent development program to enhance your career with us.
- Culture - We are believers in maintaining a healthy work-life balance. While we work hard and care deeply about our customers and partners, we want you to have room for your family, friends, and yourself.
- Growth - Company growth provides unprecedented career growth. FHF’s extraordinary year over year growth in revenue and new markets provides opportunity for you to establish and develop your career growth. We engage each employee to build a career plan that benefits everyone and we have a proven record of investing in you.
Diversity and Inclusion
FHF is committed to building a culture that respects and embraces all walks of life, inclusive of gender, race, culture, age, sexual orientation, and other identities. We will make accommodations when interviewing anyone with special needs.
Sales #TerritorySales #OutsideSales #B2BSales #AccountManager
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Find Sales Representative JobsSales Representative Job Market in Chicago
Who's Hiring
- Uber12

- Braze10

- Rippling9

- SentiLink9

- Salesforce7

Top Industries Hiring
- Technology & Software149
- Consulting & Professional Services29
- Marketing & Advertising17
- Insurance15
- Medical Devices14
Sales Representative Jobs in Chicago: Frequently Asked Questions
How do I get a sales representative job in Chicago?
Focus your search on Chicago's strongest hiring sectors: enterprise software and SaaS companies clustered in the Loop and River North, medical device and life sciences firms on the North Side, and financial services firms anchored downtown. Candidates who demonstrate familiarity with Chicago's B2B landscape and can show a consistent book of business or verifiable quota attainment stand out most with local hiring managers.
Which companies hire sales representatives in Chicago?
Employers hiring sales representatives in Chicago right now include Uber, Braze, and Rippling, based on current listings on Migrate Mate as of June 2026. Chicago's market includes a deep mix of Fortune 500 headquartered companies, regional distributors, and fast-growing SaaS and healthtech startups, many concentrated in the Loop, River North, and Fulton Market corridors.
Are there remote sales representative jobs in Chicago?
Yes, though remote availability varies by role type. About 51% of sales representative openings tied to Chicago are remote or hybrid as of June 2026, with inside sales and SaaS account executive roles most commonly offered in remote or hybrid arrangements. Field and territory sales roles tied to Chicago's manufacturing, distribution, and healthcare accounts typically require in-person client coverage.
How can I get a sales representative job in Chicago with little or no experience?
The most realistic entry point in Chicago is a sales development representative or business development representative role, which many River North and Loop-based SaaS and tech companies use as a structured entry-level pipeline. Staffing and commercial insurance firms in the metro also hire entry-level candidates with strong communication skills and train on the job. A demonstrated interest in Chicago's dominant industries, technology or healthcare for example, sharpens your candidacy noticeably.
Which industries hire the most sales representatives in Chicago?
The sectors hiring the most sales representatives in Chicago are Technology & Software, Consulting & Professional Services, and Marketing & Advertising, based on current listings on Migrate Mate as of June 2026. Chicago's role as a Midwest commercial hub and home to major corporate headquarters in finance, logistics, and healthcare technology makes it one of the densest markets in the country for B2B and enterprise sales talent.
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