Inside Sales Representative Jobs in Chicago, IL
Inside Sales Representative jobs in Chicago are concentrated in the Loop, River North, and the Fulton Market District, with strong demand across software, financial services, and healthcare technology. Employers hiring right now include WM, Yelp, and Asana. See the openings below and apply to the ones that match your experience.
Find JobsOverview
Showing 5 of 97+ Inside Sales Representative jobs











Shift: 1st Shift
Work model: On-Site
Schedule: FULLTIME; Monday-Friday, 8:00 a.m.-5:00 p.m
*Now Hiring for January and June*
Job overview:
Schneider is seeking an Inside Sales Representative in Chicago, IL to close deals with new businesses and manage existing accounts within Schneider's Transportation Management (STM) division. This role focuses on developing key contacts within their book of business to generate revenue and exceed sales goals through analysis.
Responsibilities:
- Become an expert during our comprehensive training program and learn how we effectively service our customers.
- Expand your book of business by prospecting, cold calling, identifying and developing opportunities through a holistic customer service approach.
- Utilize state of the art technology by providing clear solutions to your customers and influencing them to utilize our best-in-class tools and resources.
- Reach and exceed sales goals by focusing on business growth opportunities.
Skills and qualifications
- Can manage multiple priorities while working with minimal direction.
- Have a strong technical aptitude.
- Have outstanding communication skills and strong attention to detail.
- Be results-driven.
Pay and benefits
- Financial freedom - Earn a competitive base wage plus a generous incentive plan.
- Unlimited growth opportunities - Grow and advance your career with over 170 instructor and/or self-led courses.
- Flexibility - Enjoy a supportive work-life balance. Associates will be provided partial scheduled remote options after one year in role dependent upon associate meeting the performance expectations of the role.
- Generous benefits - Take advantage of paid time off, paid holidays, tuition assistance, health care, 401(k) with company match and more!
- Starting wages are $21.60 - $27.00 per hour based on experience.
Schneider's inclusive culture
Our history has taught us that treating everyone with dignity and respect is vital to our ongoing success. We embrace and seek out diversity that is inclusive of thought, race, ethnicity, national origin, sex, gender, gender expression, age, religion, sexual orientation, ability, medical condition, veteran or military status, experience and background. This diversity and openness ensures all associates have equal access to opportunities and resources to contribute fully to the organization's success, and it fuels innovation, improves strategic thinking and cultivates leadership. Any applicant may request a reasonable accommodation to complete a job application, pre-employment testing, or job interview or to otherwise participate in the hiring process consistent with the Americans with Disabilities Act (ADA) by contacting their Recruiter, Human Resources Business Partner, and/or Human Resources Leave Administration.
PI286907422
See All 97 Inside Sales Representative Jobs in Chicago
Find roles in Chicago that match your experience and apply in just a few clicks.
Find JobsInside Sales Representative Job Market in Chicago
Who's Hiring



Top Industries Hiring
- Insurance
- Automotive
Inside Sales Representative Jobs in Chicago: Frequently Asked Questions
How do I get a inside sales representative job in Chicago?
Focus your search on Chicago's software, fintech, and healthcare technology sectors, which generate the most inside sales openings in the city. The Loop and River North hold the highest concentration of employers, while Fulton Market has become a hotspot for growth-stage tech companies. Candidates who can demonstrate experience with CRM tools and a history of hitting quota in a B2B environment stand out most in this market.
Which companies hire inside sales representatives in Chicago?
Employers hiring inside sales representatives in Chicago right now include WM, Yelp, and Asana, based on current listings on Migrate Mate as of September 2026. Chicago's hiring mix leans toward mid-size SaaS companies, regional financial services firms, and national healthcare organizations with sales operations headquartered or expanded in the city.
Are there remote inside sales representative jobs in Chicago?
Yes, inside sales is one of the more remote-friendly roles in sales since the work is phone and screen-based rather than field-based. About 70% of inside sales representative openings tied to Chicago are remote or hybrid as of September 2026, reflecting how broadly Chicago employers have adopted flexible arrangements. Outbound prospecting and account development roles tend to offer the most remote flexibility locally.
How can I get a inside sales representative job in Chicago with little or no experience?
The most realistic entry path in Chicago is landing a sales development representative or business development representative role, which are common at the city's SaaS and fintech companies as structured stepping stones into inside sales. Chicago employers like mid-size software firms and insurance companies frequently hire candidates without formal sales experience if they show strong communication skills and a willingness to work a high-volume pipeline. Completing a Chicago-based sales bootcamp or earning a HubSpot or Salesforce certification also makes entry-level candidates more competitive locally.
Which industries hire the most inside sales representatives in Chicago?
Most inside sales representative openings in Chicago sit in Insurance and Automotive, per current listings on Migrate Mate as of September 2026. Chicago's role as a national hub for financial technology, enterprise software, and large healthcare networks makes it a consistently active market for inside sales talent across those sectors.
Related Jobs in Illinois
See All 97 Inside Sales Representative Jobs in Chicago
Find roles in Chicago that match your experience and apply in just a few clicks.
Find Jobs