Customer Success Director Jobs in Chicago, IL

Customer Success Director jobs in Chicago are in strong demand, concentrated in the Loop, River North, and Fulton Market across enterprise SaaS, financial services, and healthcare technology. Employers hiring right now include Braze, SPINS, and Stripe. See the openings below and apply to the ones that match your experience.

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Overview

Open roles81
Top employerBraze
Work type53% Hybrid
Companies hiring49

Showing 5 of 81+ Customer Success Director jobs

Too Good To Go
Enterprise Customer Success Manager
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Too Good To Go
Added 4d ago
Enterprise Customer Success Manager
Too Good To Go
Chicago, Illinois
Business Development
Growth Marketing
Marketing
$85k - $100k/yr
Hybrid
Bachelor's degree in business

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Wonderlic
Senior Customer Success Manager
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Wonderlic
Added 4d ago
Senior Customer Success Manager
Wonderlic
Chicago, Illinois
AI (Artificial Intelligence)
Data Science
ML (Machine Learning)
Remote (US)
51-200

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Braze
Customer Success Manager II, Enterprise
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Braze
Added 4d ago
Customer Success Manager II, Enterprise
Braze
Chicago, Illinois
Customer Support
IT Support
Technical Program Management
$95k - $120k/yr
1,001-5,000

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Meltwater
Customer Success Manager
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Meltwater
Added 5d ago
Customer Success Manager
Meltwater
Chicago, Illinois
Business Operations
Executive Leadership & C-Suite
Project Management
$48k - $64k/yr
Hybrid
Bachelor's degree
1,001-5,000

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Cargomatic
Customer Success Specialist
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Cargomatic
Added 6d ago
Customer Success Specialist
Cargomatic
Chicago, Illinois
Account Management
Business Development
Sales
$60k - $75k/yr
On-Site
Bachelor's degree
201-500

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See All 81 Customer Success Director Jobs in Chicago

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

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Customer Success Director Job Market in Chicago

Who's Hiring

Braze
Braze4 open roles
SPINS
SPINS3 open roles
Stripe
Stripe3 open roles

Top Industries Hiring

  • Technology & Software10
  • Banking & Financial Services4
  • Marketing & Advertising1

Customer Success Director Jobs in Chicago: Frequently Asked Questions

How do I get a customer success director job in Chicago?

Focus your search on Chicago's enterprise SaaS companies in Fulton Market and River North, the major financial services firms in the Loop, and the growing health tech corridor near the Illinois Medical District. Employers here favor candidates with demonstrated retention and expansion revenue results, familiarity with Salesforce or Gainsight, and experience managing mid-market or enterprise accounts. Networking through Chicago tech community events and local SaaS meetups gives candidates a meaningful edge.

Which companies hire customer success directors in Chicago?

Employers hiring customer success directors in Chicago right now include Braze, SPINS, and Stripe, based on current listings on Migrate Mate as of September 2026. Chicago's market is anchored by established enterprise software firms, fast-growing B2B SaaS startups, and large financial and healthcare organizations that run sizable customer success functions.

Are there remote customer success director jobs in Chicago?

Yes, though availability depends on the role's scope, since directors managing enterprise accounts or cross-functional teams are often expected on-site or hybrid. About 83% of customer success director openings tied to Chicago are remote or hybrid as of September 2026, reflecting broader flexibility in the tech and SaaS sectors. Strategic and program-management-heavy CS director roles tend to offer the most remote flexibility among Chicago listings.

How can I get a customer success director job in Chicago with little or no experience?

The most realistic path is moving up from a senior customer success manager role at one of Chicago's mid-size SaaS or fintech companies, where director openings often promote from within. Companies in Fulton Market and the Merchandise Mart tech cluster frequently hire senior ICs ready to step into leadership. Building a track of measurable churn reduction or net revenue retention and taking on team-lead responsibilities in your current role strengthens a director-level application significantly.

Which industries hire the most customer success directors in Chicago?

Chicago customer success director roles concentrate in Technology & Software, Banking & Financial Services, and Marketing & Advertising, based on current listings on Migrate Mate as of September 2026. Chicago's dense base of enterprise software vendors, commodities and financial technology firms, and large hospital systems and insurers all maintain significant customer success functions that regularly need director-level leadership.

See All 81 Customer Success Director Jobs in Chicago

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