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 Northern Trust, Advyzon, and SentiLink. Scan the live roles below and apply to whichever ones fit.

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Overview

Open roles78
Top employerNorthern Trust
Work type44% Hybrid
Top credentialMaster's degree in business administration
Companies hiring44

Showing 5 of 78+ Head Of Sales jobs

Keyrock
Head of Marketing (Director)
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Keyrock
Added 1d ago
Head of Marketing (Director)
Keyrock
Chicago, Illinois
Brand Marketing
Growth Marketing
Marketing
Hybrid
11-50

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OLD MISSION
Associate Head of Trader Education
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OLD MISSION
Added 2d ago
Associate Head of Trader Education
OLD MISSION
Chicago, Illinois
Business Development
Growth Marketing
Marketing
$175k - $200k/yr

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HBF
Head of Product, Textiles & Furniture
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HBF
Added 2d ago
Head of Product, Textiles & Furniture
HBF
Chicago, Illinois
Brand Marketing
Growth Marketing
Marketing
Master's degree in business administration
501-1,000

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TransUnion
Vice President, Head of U.S. Compliance Advisory
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TransUnion
Added 2d ago
Vice President, Head of U.S. Compliance Advisory
TransUnion
Chicago, Illinois
Human Resources
Human Resources (HR) — Generalist
Learning & Development
Recruiting & Talent Acquisition
$194k - $407k/yr
Hybrid
Bachelor's degree
10,000+

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Enova International
Head of Consumer Partnerships Marketing (Hybrid)
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Enova International
Added 2d ago
Head of Consumer Partnerships Marketing (Hybrid)
Enova International
Chicago, Illinois
Account Management
Customer Service
Customer Success
$130k - $190k/yr
Hybrid
Bachelor's degree in marketing
1,001-5,000

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See All 78 Head Of Sales Jobs in Chicago

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

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Head Of Sales Job Market in Chicago

Who's Hiring

Northern Trust
Northern Trust6 open roles
Advyzon
Advyzon4 open roles
SentiLink
SentiLink4 open roles

Top Industries Hiring

  • Technology & Software
  • Investment & Asset Management
  • Biotechnology & Pharmaceuticals
  • Food & Beverage
  • Medical Devices

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 Northern Trust, Advyzon, and SentiLink, per current listings on Migrate Mate as of August 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 71% of head of sales openings tied to Chicago are remote or hybrid as of August 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, Investment & Asset Management, and Biotechnology & Pharmaceuticals, based on current listings on Migrate Mate as of August 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 78 Head Of Sales Jobs in Chicago

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