Sales Leader Jobs in Chicago, IL

Sales Leader jobs in Chicago are in strong demand, concentrated in the Loop, River North, and Fulton Market across financial services, technology, and healthcare. Employers actively hiring include KI, Telus, and Bonobos. Scan the live roles below and apply to whichever ones fit.

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Overview

Open roles74
Top employerKI
Work type100% On-site
Top credentialBachelor's degree
Companies hiring13

Showing 5 of 74+ Sales Leader jobs

Sales Leader, Retirement & Benefit Solutions
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New 22h ago
Sales Leader, Retirement & Benefit Solutions
Koers Bedrijfspsychologie
Chicago, Illinois
Business Development
Business Strategy
Partnerships & Business Development
$106k - $215k/yr

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Retail Sales Team Leader (Full-Time with benefits, specialty foods)
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Added 4d ago
Retail Sales Team Leader (Full-Time with benefits, specialty foods)
The Spice House
Chicago, Illinois
Business Strategy
Marketing
Product Management
$18 - $19/hr
51-200

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Senior Sales Operations Transformation & Managed Services Leader
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Added 4d ago
Senior Sales Operations Transformation & Managed Services Leader
Logic, Inc.
Chicago, Illinois
Account Management
Customer Service
Customer Success
$123k - $246k/yr
Military encouraged
11-50

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Vice President, National Opportunity Geography Sales Leader
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Added 1mo ago
Vice President, National Opportunity Geography Sales Leader
Chubb Insurance
Chicago, Illinois
Customer Service
Customer Success
Customer Support
Bachelor's degree
10,000+

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Retail Sales Leader
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Added 1mo ago
Retail Sales Leader
Bonobos
Chicago, Illinois
Compliance & Legal
Compliance & Risk
Security & Protective Services
$24 - $32/hr
201-500

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See All 74 Sales Leader Jobs in Chicago

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

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Sales Leader Job Market in Chicago

Who's Hiring

KI6 open roles
Telus6 open roles
Bonobos6 open roles

Top Industries Hiring

  • Technology & Software

Sales Leader Jobs in Chicago: Frequently Asked Questions

How do I get a sales leader job in Chicago?

Target Chicago's strongest hiring corridors: fintech and insurtech firms in the Loop, SaaS and cloud companies in River North and Fulton Market, and health systems on the Near North Side. Candidates with enterprise B2B experience and a demonstrated ability to build Chicago-area pipeline stand out. Attending local revenue leadership meetups and connecting with hiring managers at Chicago-headquartered firms accelerates the search considerably.

Which companies hire sales leaders in Chicago?

Companies currently hiring sales leaders in Chicago include KI, Telus, and Bonobos, per current listings on Migrate Mate as of November 2026. Chicago's mix of Fortune 500 headquarters, fast-scaling mid-market tech firms, and large regional insurers means demand comes from a wide range of employer types across the city.

Are there remote sales leader jobs in Chicago?

Yes, though remote availability depends heavily on the role, since sales leaders managing local teams or territory-based accounts typically require an on-site or hybrid presence. About 0% of sales leader openings tied to Chicago are remote or hybrid as of November 2026, with remote arrangements most common in SaaS and enterprise software companies headquartered downtown.

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

The most realistic entry path in Chicago is stepping into a senior individual contributor role first, typically an account executive or senior sales representative position at a mid-market tech or insurance firm, then transitioning into a team lead title within 12 to 18 months. Chicago's dense SaaS corridor in River North and Fulton Market regularly promotes strong closers into their first leadership role from within.

Which industries hire the most sales leaders in Chicago?

Chicago sales leader roles concentrate in Technology & Software, based on current listings on Migrate Mate as of November 2026. Chicago's position as a national hub for financial services, enterprise software, and healthcare administration keeps consistent demand for sales leadership talent across all three sectors throughout the year.

See All 74 Sales Leader Jobs in Chicago

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