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.

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Overview

Open roles97
Top employerWM
Work type60% Remote
Top credentialBachelor's degree
Companies hiring16

Showing 5 of 97+ Inside Sales Representative jobs

Schneider
Inside Sales Representative
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Schneider
Added 2d ago
Inside Sales Representative
Schneider
Chicago, Illinois
Account Management
Customer Service
Customer Success
$21.6 - $27/hr
On-Site
10,000+

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Asana
Inside Sales Representative (Chicago)
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Asana
Added 4d ago
Inside Sales Representative (Chicago)
Asana
Chicago, Illinois
Account Management
Inside Sales
Sales
Remote (US)
1,001-5,000

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Alpine Home Air Products
Consultative Inside Sales Representative
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Alpine Home Air Products
Added 5d ago
Consultative Inside Sales Representative
Alpine Home Air Products
Chicago, Illinois
Account Management
Customer Service
Sales
Remote (US)
51-200

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Sabert
Inside Sales Representative
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Sabert
Added 6d ago
Inside Sales Representative
Sabert
Chicago, Illinois
Business Operations
Customer Service
Customer Success
Bachelor's degree in communications
1,001-5,000

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Par Health
Inside Sales Representative
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Par Health
Added 1w ago
Inside Sales Representative
Par Health
Chicago, Illinois
Sales
Account Management
Inside Sales
$53k - $70k
On-Site
Bachelor's

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See All 97 Inside Sales Representative Jobs in Chicago

Find roles in Chicago that match your experience and apply in just a few clicks.

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Inside Sales Representative Job Market in Chicago

Who's Hiring

WM
WM6 open roles
Yelp
Yelp6 open roles
Asana
Asana6 open roles

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.

See All 97 Inside Sales Representative Jobs in Chicago

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