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 Fortinet, Sprout Social, and Box. Scan the live roles below and apply to whichever ones fit.

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Overview

Open roles28
Top employerFortinet
Work type40% Remote
Companies hiring21

Showing 5 of 28+ Enterprise Sales Director jobs

Director, Enterprise Sales (Public Sector)
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Added 4d ago
Director, Enterprise Sales (Public Sector)
Sprout Social
Chicago, Illinois
Business Development
Business Strategy
Customer Success
Partnerships & Business Development
$264k - $436k/yr
Remote (US)
1,001-5,000

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Director, Enterprise Sales
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Added 4d ago
Director, Enterprise Sales
Sprout Social
Chicago, Illinois
Business Development
Business Strategy
Customer Success
Partnerships & Business Development
$264k - $436k/yr
Remote (US)
1,001-5,000

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Enterprise AI Architecture Director
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Added 6d ago
Enterprise AI Architecture Director
Information Technology Senior Management Forum
Chicago, Illinois
Business Development
Executive Leadership & C-Suite
Partnerships & Business Development
$123k - $338k/yr
Military encouraged
51-200

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Enterprise AI Architecture Director
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Added 6d ago
Enterprise AI Architecture Director
Logic, Inc.
Chicago, Illinois
Consulting & Professional Services
Software Engineering
Solutions Engineering & Architecture
Technical Program Management
$123k - $338k/yr
Military encouraged
11-50

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Sr. Director, Enterprise Growth Partnerships Strategy & Scaling
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Added 6d ago
Sr. Director, Enterprise Growth Partnerships Strategy & Scaling
Mars
Chicago, Illinois
Clinical Support
Healthcare Administration
Medical Specialists
$193k - $265k/yr
Bachelor's degree in communications
10,000+

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See All 28 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

Fortinet2 open roles
Sprout Social2 open roles
Box1 open role

Top Industries Hiring

  • Technology & Software
  • Distribution & Wholesale
  • 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 Fortinet, Sprout Social, and Box and others right now, based on current listings on Migrate Mate as of November 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 73% of enterprise sales director openings tied to Chicago are remote or hybrid as of November 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, Distribution & Wholesale, and Consulting & Professional Services, based on current listings on Migrate Mate as of November 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 28 Enterprise Sales Director Jobs in Chicago

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