Enterprise Sales Specialist Jobs in Chicago, IL

Enterprise Sales Specialist jobs in Chicago are in strong demand, concentrated in the Loop, River North, and the Fulton Market district across enterprise software, financial technology, healthcare technology, and professional services. Employers actively hiring include Meta, Amazon Web Services, and Datadog. See the openings below and apply to the ones that match your experience.

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Overview

Open roles22
Top employerMeta
Work type67% On-site
Top credentialBachelor's
Companies hiring14

Showing 5 of 22+ Enterprise Sales Specialist jobs

Google
Workspace Sales Specialist II, Enterprise Greenfield, Google Cloud
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Google
Added 1w ago
Workspace Sales Specialist II, Enterprise Greenfield, Google Cloud
Google
Chicago, Illinois
Sales
$116k - $170k/yr
Bachelor's
10,000+

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Nutanix
NDB Portfolio Sales Specialist - Enterprise - Central
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Nutanix
Added 3w ago
NDB Portfolio Sales Specialist - Enterprise - Central
Nutanix
Chicago, Illinois
Sales
Account Management
Partnerships & Business Development
Enterprise Sales
Business Development
5,001-10,000

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Samsara
Specialist Seller - Enterprise Select AI Products
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Samsara
Added 3w ago
Specialist Seller - Enterprise Select AI Products
Samsara
Chicago, Illinois
Sales
Partnerships & Business Development
Enterprise Sales
Business Development
$350k/yr
Remote (US)
None
1,001-5,000

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Meta
Enterprise Technical Sales Specialist, NORAM
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Meta
Added 1mo ago
Enterprise Technical Sales Specialist, NORAM
Meta
Chicago, Illinois
Sales
Partnerships & Business Development
Enterprise Sales
Business Development
$177k - $247k/yr
Bachelor's
10,000+

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Meta
Enterprise Technical Sales Specialist (NORAM)
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Meta
Added 1mo ago
Enterprise Technical Sales Specialist (NORAM)
Meta
Chicago, Illinois
Sales
Partnerships & Business Development
Enterprise Sales
Business Development
$107k - $169k/yr
Bachelor's
10,000+

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See All 22 Enterprise Sales Specialist Jobs in Chicago

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

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Enterprise Sales Specialist Job Market in Chicago

Who's Hiring

  • Meta
    Meta6
  • Amazon Web Services
    Amazon Web Services3
  • Datadog
    Datadog2
  • Google
    Google1
  • Nutanix
    Nutanix1

Top Industries Hiring

  • Technology & Software10
  • Distribution & Wholesale3
  • Consulting & Professional Services2
  • Education1
  • Cybersecurity1

Enterprise Sales Specialist Jobs in Chicago: Frequently Asked Questions

How do I get an enterprise sales specialist job in Chicago?

Focus your search on Chicago's Loop and River North corridors, where enterprise software, fintech, and B2B SaaS companies concentrate their sales teams. Familiarity with complex, multi-stakeholder deal cycles and experience selling into financial services or healthcare gives candidates a clear edge in this market. Networking through Chicago-area tech and sales communities and targeting employers with Midwest regional headquarters also accelerates the process.

Which companies hire enterprise sales specialists in Chicago?

Chicago enterprise sales specialist roles are posted by Meta, Amazon Web Services, and Datadog and others right now, based on current listings on Migrate Mate as of June 2026. Chicago's mix of legacy enterprise technology firms, fast-growing B2B SaaS companies, and large financial institutions creates consistent demand for enterprise sales talent across a wide range of employer sizes.

Are there remote enterprise sales specialist jobs in Chicago?

Yes, though enterprise sales roles are less fully remote than most desk-based positions because client relationship-building and on-site presentations remain central to closing large deals. About 33% of enterprise sales specialist openings tied to Chicago are remote or hybrid as of June 2026, reflecting hybrid structures that blend in-office collaboration with flexible client travel. Prospecting and pipeline management work are the functions most commonly handled remotely.

How can I get an enterprise sales specialist job in Chicago with little or no experience?

The most realistic entry path is landing a sales development representative or inside sales role at one of Chicago's many B2B software or fintech companies, where structured training and clear promotion tracks into enterprise roles are common. Companies in Fulton Market and River North frequently hire junior sales talent and develop them internally. Demonstrating comfort with long sales cycles, CRM tools, and Chicago's financial services client base will set you apart early.

Which industries hire the most enterprise sales specialists in Chicago?

The sectors hiring the most enterprise sales specialists in Chicago are Technology & Software, Distribution & Wholesale, and Consulting & Professional Services, based on current listings on Migrate Mate as of June 2026. Chicago's status as a major financial hub and a growing technology center drives concentrated demand from large institutional buyers who require dedicated enterprise sales coverage.

See All 22 Enterprise Sales Specialist Jobs in Chicago

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