Enterprise Sales Director Jobs in Chicago, IL

Enterprise Sales Director jobs in Chicago are concentrated in the Loop, River North, and Fulton Market, with strong demand across enterprise software, financial services, and healthcare technology. Companies actively hiring include Workday, Near North Health Service Corporation, and Giga. Scan the live roles below and apply to whichever ones fit.

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Overview

Open roles16
Top employerWorkday
Work type43% On-site
Companies hiring12

Showing 5 of 16+ Enterprise Sales Director jobs

Hyatt
Senior Global Sales Director, Global Enterprise & Transient (Remote)
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Hyatt
Added 6d ago
Senior Global Sales Director, Global Enterprise & Transient (Remote)
Hyatt
Chicago, Illinois
Account Management
Customer Service
Customer Success
$120k - $160k/yr
Remote (US)
Bachelor's degree in business
10,000+

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ABM Industries Inc.
Senior Director, Technology - Enterprise Service Operation & Delivery
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ABM Industries Inc.
Added 2w ago
Senior Director, Technology - Enterprise Service Operation & Delivery
ABM Industries Inc.
Chicago, Illinois
Customer Service
Customer Success
Customer Support
$144k - $200k/yr
Master's degree in business administration
10,000+

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Workday
Regional Sales Director, Large Enterprise Customer Base
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Workday
Added 2w ago
Regional Sales Director, Large Enterprise Customer Base
Workday
Chicago, Illinois
Customer Service
Customer Success
Customer Support
$174k - $261k/yr
10,000+

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Near North Health Service Corporation
Director of Enterprise Data, Analytics, and Evaluation
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Near North Health Service Corporation
Added 3w ago
Director of Enterprise Data, Analytics, and Evaluation
Near North Health Service Corporation
Chicago, Illinois
Customer Service
Customer Support
Hospitality & Guest Services
$100k - $125k/yr
51-200

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Intelas
Clinical Engineering Enterprise Director
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Intelas
Added 3w ago
Clinical Engineering Enterprise Director
Intelas
Chicago, Illinois
Business Analysis
Business Strategy
Strategy & Corporate Development
$165k - $190k/yr
ISO certification process
1,001-5,000

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See All 16 Enterprise Sales Director Jobs in Chicago

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

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Enterprise Sales Director Job Market in Chicago

Who's Hiring

Workday
Workday2 open roles
Near North Health Service Corporation
Near North Health Service Corporation2 open roles
Giga
Giga1 open role

Top Industries Hiring

  • Technology & Software
  • Consulting & Professional Services

Enterprise Sales Director Jobs in Chicago: Frequently Asked Questions

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

Target Chicago's heaviest hiring sectors first: enterprise software, fintech, and healthcare IT, where director-level sales roles turn over most frequently. The Loop and River North hold the densest concentration of regional headquarters and mid-market SaaS firms. Candidates who can demonstrate ownership of complex, multi-stakeholder deals and a history closing seven-figure enterprise contracts stand out most in Chicago's competitive market.

Which companies hire enterprise sales directors in Chicago?

Chicago enterprise sales director roles are posted by Workday, Near North Health Service Corporation, and Giga and others right now, based on current listings on Migrate Mate as of September 2026. Chicago's mix of global Fortune 500 headquarters, fast-scaling SaaS companies, and regional financial services firms creates consistent demand for enterprise sales leadership across company sizes.

Are there remote enterprise sales director jobs in Chicago?

Yes, though enterprise sales director roles are moderately remote-friendly since the work involves significant client relationship management and in-person deal cycles. About 57% of enterprise sales director openings tied to Chicago are remote or hybrid as of September 2026, with the remote-eligible roles most often covering named-account or territory-based books where travel substitutes for a fixed office.

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

The most realistic entry path in Chicago is moving up from a senior account executive or regional sales manager role at a local SaaS, fintech, or healthcare IT company, where promotion into director-level titles is common. Chicago-based mid-market software firms and growth-stage startups in Fulton Market and the West Loop frequently promote from within. Building a verifiable pipeline record and experience with enterprise procurement cycles gives candidates the strongest footing locally.

Which industries hire the most enterprise sales directors in Chicago?

Chicago enterprise sales director roles concentrate in Technology & Software and Consulting & Professional Services, based on current listings on Migrate Mate as of September 2026. Chicago's position as a national hub for financial services, healthcare networks, and a growing enterprise software corridor makes those sectors the steadiest and most volume-consistent sources of director-level sales hiring in the city.

See All 16 Enterprise Sales Director Jobs in Chicago

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