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, Wolters Kluwer, and Stripe. See the openings below and apply to the ones that match your experience.

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Overview

Open roles79
Top employerBraze
Work type71% Hybrid
Top credentialBachelor's degree
Companies hiring45

Showing 4 of 79+ Customer Success Director jobs

Customer Success Representative
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Added 2d ago
Customer Success Representative
MVP One
Chicago, Illinois
Customer Service
Customer Service & Support
Customer Support
$52k - $80k/yr
Hybrid
Bachelor's degree
51-200

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Technical Customer Success Manager
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Added 3d ago
Technical Customer Success Manager
SyndiGO
Chicago, Illinois
Account Management
Business Development
Business Strategy
$72k - $80k/yr
Hybrid
51-200

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Customer Success Manager
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Added 3d ago
Customer Success Manager
SyndiGO
Chicago, Illinois
Account Management
Business Development
Business Strategy
$72k - $80k/yr
Hybrid
51-200

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Customer Success Team Lead
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Added 4d ago
Customer Success Team Lead
World Book
Chicago, Illinois
Business Development
Customer Success
Sales
Remote (US)
Bachelor's degree
51-200

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See All 79 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

Braze5 open roles
Wolters Kluwer5 open roles
Stripe3 open roles

Top Industries Hiring

  • Technology & Software
  • Banking & Financial Services
  • Consulting & Professional Services

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, Wolters Kluwer, and Stripe, based on current listings on Migrate Mate as of November 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 90% of customer success director openings tied to Chicago are remote or hybrid as of November 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 Consulting & Professional Services, based on current listings on Migrate Mate as of November 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 79 Customer Success Director Jobs in Chicago

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