Customer Success Representative Jobs in Chicago, IL
Customer Success Representative jobs in Chicago are concentrated in the Loop, River North, and Fulton Market, driven by strong demand from SaaS companies, fintech firms, and healthcare technology employers. Braze, Wolters Kluwer, and Stripe are among those actively posting right now. See the openings below and apply to the ones that match your experience.
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Senior Customer Success Manager
Location: United States – Remote
Job Type: Full-Time
Experience Level: Senior-Level
Job Overview
We are seeking an experienced Senior Customer Success Manager to oversee strategic customer relationships, drive customer retention, and support long-term business growth. The ideal candidate has extensive SaaS experience, strong account management skills, and a proven record of professional stability.
Key Responsibilities
- Manage strategic customer accounts and maintain long-term client relationships.
- Lead customer onboarding, retention, and account growth initiatives.
- Coordinate with sales, product, and technical teams to resolve customer needs.
- Manage customer data and workflows using Salesforce and CRM platforms.
- Analyze account performance, identify risks, and recommend solutions.
- Improve customer satisfaction, retention, and business outcomes.
Qualifications
- 8–10+ years of relevant professional experience in customer success, account management, or SaaS operations.
- At least 5 consecutive years of employment with the same company, demonstrating professional stability and career progression.
- Strong experience in enterprise account management and customer relationship development.
- Advanced proficiency in Salesforce, CRM systems, and Microsoft Office.
- Excellent communication, analytical, project management, and problem-solving skills.
- Ability to manage multiple accounts independently in a remote work environment.
Preferred Qualifications
- Experience managing enterprise SaaS accounts.
- Background in customer retention and revenue growth.
- Experience coordinating cross-functional projects.
- Demonstrated record of long-term professional achievement.
What We Value
Professional integrity, long-term commitment, strategic thinking, customer-focused leadership, and measurable business results.
Pay: $88,200.00 - $99,000.00 per year
Benefits:
- 401(k)
- 401(k) matching
- Employee assistance program
- Employee discount
- Flexible spending account
- Happy hour
- Health insurance
- Health savings account
- Life insurance
- On-site gym
- Paid time off
- Paid training
- Parental leave
- Relocation assistance
- Retirement plan
- Tuition reimbursement
- Vision insurance
- Volunteer time off
- Work from home
Work Location: Remote
Senior Customer Success Manager
Location: United States – Remote
Job Type: Full-Time
Experience Level: Senior-Level
Job Overview
We are seeking an experienced Senior Customer Success Manager to oversee strategic customer relationships, drive customer retention, and support long-term business growth. The ideal candidate has extensive SaaS experience, strong account management skills, and a proven record of professional stability.
Key Responsibilities
- Manage strategic customer accounts and maintain long-term client relationships.
- Lead customer onboarding, retention, and account growth initiatives.
- Coordinate with sales, product, and technical teams to resolve customer needs.
- Manage customer data and workflows using Salesforce and CRM platforms.
- Analyze account performance, identify risks, and recommend solutions.
- Improve customer satisfaction, retention, and business outcomes.
Qualifications
- 8–10+ years of relevant professional experience in customer success, account management, or SaaS operations.
- At least 5 consecutive years of employment with the same company, demonstrating professional stability and career progression.
- Strong experience in enterprise account management and customer relationship development.
- Advanced proficiency in Salesforce, CRM systems, and Microsoft Office.
- Excellent communication, analytical, project management, and problem-solving skills.
- Ability to manage multiple accounts independently in a remote work environment.
Preferred Qualifications
- Experience managing enterprise SaaS accounts.
- Background in customer retention and revenue growth.
- Experience coordinating cross-functional projects.
- Demonstrated record of long-term professional achievement.
What We Value
Professional integrity, long-term commitment, strategic thinking, customer-focused leadership, and measurable business results.
Pay: $88,200.00 - $99,000.00 per year
Benefits:
- 401(k)
- 401(k) matching
- Employee assistance program
- Employee discount
- Flexible spending account
- Happy hour
- Health insurance
- Health savings account
- Life insurance
- On-site gym
- Paid time off
- Paid training
- Parental leave
- Relocation assistance
- Retirement plan
- Tuition reimbursement
- Vision insurance
- Volunteer time off
- Work from home
Work Location: Remote
See All 76 Customer Success Representative Jobs in Chicago
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Find JobsCustomer Success Representative Job Market in Chicago
Who's Hiring
Top Industries Hiring
- Technology & Software
- Banking & Financial Services
Customer Success Representative Jobs in Chicago: Frequently Asked Questions
How do I get a customer success representative job in Chicago?
Focus your search on Chicago's SaaS, fintech, and healthtech sectors, which consistently post the highest volume of customer success roles in the city. The Loop and Fulton Market corridor are the densest hiring zones. Candidates who can demonstrate CRM proficiency, low churn metrics from prior roles, and familiarity with B2B client relationships tend to stand out in Chicago's competitive, enterprise-heavy market.
Which companies hire customer success representatives in Chicago?
Chicago customer success representative roles are posted by Braze, Wolters Kluwer, and Stripe and others right now, based on current listings on Migrate Mate as of November 2026. Chicago's mix of homegrown tech companies, national financial services firms, and growing healthcare technology organizations means openings come from a wide range of employer sizes and industries.
Are there remote customer success representative jobs in Chicago?
Yes, customer success representative work is well-suited to remote and hybrid arrangements since most client interaction happens over phone, email, and video. About 84% of customer success representative openings tied to Chicago are remote or hybrid as of November 2026, reflecting broad adoption across the city's tech and SaaS employers. Fully on-site roles are more common at Chicago-area companies that prioritize in-person client relationship management.
How can I get a customer success representative job in Chicago with little or no experience?
The most realistic entry path in Chicago is through a customer support or account coordinator role at one of the city's many mid-size SaaS or fintech companies, which regularly hire and promote from within. Chicago employers in Fulton Market and the West Loop often value demonstrated communication skills and CRM familiarity over years of experience. Completing a Salesforce or HubSpot certification and targeting companies with structured onboarding programs gives entry-level candidates a concrete advantage.
Which industries hire the most customer success representatives in Chicago?
The sectors hiring the most customer success representatives in Chicago are Technology & Software and Banking & Financial Services, based on current listings on Migrate Mate as of November 2026. Chicago's role as a major hub for enterprise software, commodities technology, and healthcare innovation creates sustained, year-round demand for customer success professionals across these industries.
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