Enterprise Sales Executive Jobs in Chicago, IL

Enterprise Sales Executive jobs in Chicago are concentrated in the Loop, River North, and Fulton Market, with strong demand from employers in enterprise software, financial services, logistics technology, and healthcare IT. Top companies hiring right now include Uber, Rippling, and SentiLink. See the openings below and apply to the ones that match your experience.

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Overview

Open roles268+
Top employerUber
Work type43% On-site
Top credentialBachelor's
Companies hiring100+

Showing 5 of 268+ Enterprise Sales Executive jobs

Anaplan
Enterprise Account Executive
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Anaplan
Added 1d ago
Enterprise Account Executive
Anaplan
Chicago, Illinois
On-Site
None
1,001-5,000

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Braze
Emerging Enterprise Account Executive
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Braze
Added 2d ago
Emerging Enterprise Account Executive
Braze
Chicago, Illinois
Sales
Account Management
Partnerships & Business Development
Enterprise Sales
Business Development
$102k - $260k/yr
Hybrid
None
1,001-5,000

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Workday
Large Enterprise Customer Base Account Executive
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Workday
Added 3d ago
Large Enterprise Customer Base Account Executive
Workday
Chicago, Illinois
Sales
Account Management
Enterprise Sales
$134k - $201k/yr
Hybrid
None
10,000+

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Amazon.com
Sr. Account Executive, Enterprise, Enterprise - Amazon Freight
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Amazon.com
Added 4d ago
Sr. Account Executive, Enterprise, Enterprise - Amazon Freight
Amazon.com
Chicago, Illinois
Sales
Account Management
Partnerships & Business Development
Business Development
Enterprise Sales
$148k - $200k/yr
10,000+

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Global Payments
Senior Account Executive - Enterprise (ANET)
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Global Payments
Added 4d ago
Senior Account Executive - Enterprise (ANET)
Global Payments
Chicago, Illinois
Sales
Account Management
Enterprise Sales
$90k - $100k/yr
Remote (US)
10,000+

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See All 268+ Enterprise Sales Executive Jobs in Chicago

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

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Enterprise Sales Executive Job Market in Chicago

Who's Hiring

  • Uber
    Uber11
  • Rippling
    Rippling9
  • SentiLink
    SentiLink9
  • Braze
    Braze8
  • Gartner
    Gartner5

Top Industries Hiring

  • Technology & Software119
  • Consulting & Professional Services17
  • Marketing & Advertising13
  • Insurance11
  • Media & Entertainment10

Enterprise Sales Executive Jobs in Chicago: Frequently Asked Questions

How do I get a enterprise sales executive job in Chicago?

Focus your search on the Loop and River North, where the highest concentration of enterprise technology, fintech, and professional services employers operate. Chicago's market rewards candidates who can demonstrate experience closing complex, multi-stakeholder deals, particularly in SaaS, logistics tech, or financial services. Building relationships through local sales communities and targeting mid-market to enterprise-stage companies headquartered or regionally based in Chicago gives you a real edge.

Which companies hire enterprise sales executives in Chicago?

Chicago enterprise sales executive roles are posted by Uber, Rippling, and SentiLink and others right now, based on current listings on Migrate Mate as of June 2026. Chicago draws a mix of globally headquartered technology firms, regional financial services companies, and fast-growing logistics and healthtech players, all of which maintain active enterprise sales teams here.

Are there remote enterprise sales executive jobs in Chicago?

Yes, though enterprise sales executive roles are moderately remote-friendly since relationship-building and client meetings often require in-person presence. About 57% of enterprise sales executive openings tied to Chicago are remote or hybrid as of June 2026, with hybrid arrangements most common among software and cloud-services companies based in the Loop and River North.

How can I get a enterprise sales executive job in Chicago with little or no experience?

The most realistic entry path in Chicago is moving up from a sales development representative or account executive role at one of the city's many mid-stage SaaS or fintech companies, where internal promotion into enterprise sales is common. Chicago employers in logistics technology and professional services also hire associate enterprise sales roles that reward strong discovery and consultative skills over tenure, making them accessible with two to three years of B2B experience.

Which industries hire the most enterprise sales executives in Chicago?

Most enterprise sales executive openings in Chicago sit in Technology & Software, Consulting & Professional Services, and Marketing & Advertising, per current listings on Migrate Mate as of June 2026. Chicago's role as a national hub for financial technology, supply chain software, and healthcare administration creates concentrated, sustained demand for enterprise sellers who can navigate long sales cycles and complex buying committees.

See All 268+ Enterprise Sales Executive Jobs in Chicago

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