Head Of Sales Jobs in Chicago, IL

Head Of Sales jobs in Chicago are in strong demand, concentrated in the Loop, River North, and Fulton Market across fintech, SaaS, healthcare technology, and B2B services. Employers hiring right now include AutoZone, Google, and Deloitte. Scan the live roles below and apply to whichever ones fit.

Find Head Of Sales Jobs

Overview

Open roles297+
Top employerAutoZone
Work type61% On-site
Top credentialBachelor's
Companies hiring100+

Showing 5 of 297+ Head Of Sales jobs

Impact Networking, LLC
Head of Growth Marketing & Delivery
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Impact Networking, LLC
Added 1d ago
Head of Growth Marketing & Delivery
Impact Networking, LLC
Chicago, Illinois
On-Site
None
501-1,000

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Screencastify
Head of Sales / Sales Manager
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Screencastify
Added 3d ago
Head of Sales / Sales Manager
Screencastify
Chicago, Illinois
Sales
Customer Service & Support
Account Management
Retail Banking & Branch Management
11-50

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Screencastify
Head of Marketing / VP of Marketing
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Screencastify
Added 3d ago
Head of Marketing / VP of Marketing
Screencastify
Chicago, Illinois
Marketing
Brand & Social Media
Content & Communications
Growth Marketing
Performance Marketing
Brand Marketing
Product Marketing
Communications
11-50

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Creative Market
Founding Head of Enterprise Sales
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Creative Market
Added 4d ago
Founding Head of Enterprise Sales
Creative Market
Chicago, Illinois
$200k - $300k/yr
Remote (US)
High School
11-50

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U.S. Bank
Head of AI Platform Engineering
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U.S. Bank
Added 1w ago
Head of AI Platform Engineering
U.S. Bank
Chicago, Illinois
AI (Artificial Intelligence)
Cloud & DevOps
Technical Program Management
Solutions Engineering & Architecture
$215k - $253k/yr
10,000+

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See All 297+ Head Of Sales Jobs in Chicago

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

Find Head Of Sales Jobs

Head Of Sales Job Market in Chicago

Who's Hiring

  • AutoZone
    AutoZone15
  • Google
    Google9
  • Deloitte
    Deloitte6
  • Okta
    Okta4
  • Uber
    Uber4

Top Industries Hiring

  • Technology & Software58
  • Manufacturing22
  • Consulting & Professional Services17
  • Automotive15
  • Investment & Asset Management13

Head Of Sales Jobs in Chicago: Frequently Asked Questions

How do I get a head of sales job in Chicago?

Focus your search on Chicago's Loop, Fulton Market, and River North corridors, where fintech, enterprise SaaS, and B2B services firms concentrate their commercial leadership hiring. Candidates with a demonstrable record of building and scaling sales teams in complex or consultative environments stand out locally. Networking through Chicago-area revenue leadership groups and targeting mid-market tech companies based in the West Loop gives you a concrete edge over applicants searching nationally.

Which companies hire head of saless in Chicago?

Companies currently hiring head of saless in Chicago include AutoZone, Google, and Deloitte, per current listings on Migrate Mate as of June 2026. Chicago's hiring base is broad, pulling from established enterprise software firms, high-growth fintech startups, and large healthcare services organizations all anchored in the city.

Are there remote head of sales jobs in Chicago?

Yes, though head of sales roles tend to be less remote-friendly than individual contributor positions because they require in-person team leadership and client relationship management. About 39% of head of sales openings tied to Chicago are remote or hybrid as of June 2026, with remote options most common at SaaS and technology companies. Strategic and analytical parts of the role, such as pipeline forecasting and territory planning, are most adaptable to remote work locally.

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

The most realistic entry path is moving up through a senior account executive or sales manager role at a Chicago-based mid-market SaaS or fintech company, where promotion to head of sales is common as teams scale. Companies in Fulton Market and River North often grow internal talent rather than hire externally for this level. Building fluency with Chicago-specific verticals like financial technology or healthcare IT, and demonstrating you can recruit and develop reps, closes the gap quickly.

Which industries hire the most head of saless in Chicago?

The sectors hiring the most head of saless in Chicago are Technology & Software, Manufacturing, and Consulting & Professional Services, based on current listings on Migrate Mate as of June 2026. Chicago's position as a national hub for financial services, enterprise technology, and healthcare administration means commercial leadership roles in these fields are consistently active across the city.

See All 297+ Head Of Sales Jobs in Chicago

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

Find Head Of Sales Jobs