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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About MVP One
MVP One is a leader in cloud-based software and solutions for asset-intensive industries, enabling teams to better manage their maintenance operations. Our user-friendly platform helps companies streamline workflows, reduce asset downtime, and optimize their human and capital resources.
About the Role
As a Customer Success Representative at MVP One, you will play a key role in driving customer retention, satisfaction, and growth by developing and maintaining strong customer relationships and proactively managing the customer experience.
In this role, you will serve as a product expert, trusted advisor, and primary point of contact for assigned accounts. You will guide customers throughout their lifecycle, from onboarding and adoption through ongoing account management and renewal. This includes independently leading Quarterly Business Reviews (QBRs), renewal meetings, and other strategic customer discussions to evaluate account health, demonstrate value, identify opportunities for improvement, and strengthen long-term relationships. You will also work closely with Sales, Support, and other internal teams to ensure customer needs are addressed and opportunities for growth and improvement are identified.
Key Responsibilities
- Develop a strong understanding of the MVP One implementation methodology and demonstrate technical proficiency with both MVP One and MP2.
- Guide new customers through the post-sale onboarding process, providing ongoing guidance to ensure successful adoption and utilization of MVP One products and services.
- Build and maintain strong customer relationships to drive user adoption, satisfaction, retention, and account growth.
- Independently prepare for and lead Quarterly Business Reviews (QBRs) with customers, evaluating system utilization, identifying adoption gaps, discussing performance metrics, and developing action plans.
- Lead customer renewal meetings, proactively addressing customer concerns, demonstrating product value, identifying retention risks, and supporting renewal and expansion efforts.
- Understand customers' business needs and maintenance objectives, providing recommendations and developing success plans that establish critical success factors, KPIs, and measurable goals.
- Monitor account health and proactively identify risks, adoption challenges, and opportunities to improve the customer experience.
- Drive customer references, testimonials, and case studies.
- Collaborate with internal teams to communicate customer feedback, resolve issues, and support product enhancements.
- Promote new products, services, and marketing initiatives, including webinars, training sessions, and events.
- Process customer orders secured by Account Executives and the Customer Success team, including:
- Schedule training and consulting services.
- Release technical support services.
- Process subscription amendments.
- Release databases.
- Update customer accounts.
- Coordinate and schedule in-person and virtual training sessions hosted by MVP One.
- Maintain accurate customer records, document interactions, and ensure timely follow-through on commitments and assigned tasks.
Preferred Qualifications/Technologies
- Bachelor's degree and/or 2+ years of experience in technology sales, customer success, or account management within the software or SaaS industries.
- Experience in manufacturing, maintenance, or facilities management is preferred.
- Flexibility to work a varied schedule with occasional overnight travel.
- Demonstrated ability to build strong customer relationships, including with senior-level stakeholders.
- Exceptional written and verbal communication skills, including the confidence and ability to independently lead customer meetings and presentations.
- Strong critical thinking and problem-solving skills, with the ability to analyze situations, identify underlying issues, and recommend appropriate solutions.
- Exceptional attention to detail and accuracy, particularly when managing customer information, processing requests, documenting interactions, and coordinating follow-up.
- Strong organizational skills and the ability to manage multiple accounts, priorities, and deadlines independently.
- Expertise in issue resolution, customer advocacy, and escalation management.
- Strong technical aptitude and the ability to quickly learn software programs, including Salesforce CRM.
- Experience in project management, particularly with software implementations.
- Ability to work effectively and collaboratively with cross-functional teams.
- Excellent time management, accountability, and follow-through.
- Bilingual in Spanish is a plus.
What We Offer
- Hybrid work schedule
- Comprehensive health benefits options beginning day one (health, dental, vision, short term disability, life insurance)
- Paid time off, including several holidays and floating holidays
- Parental leave
- Transit benefit program
- Company laptop
- Company meetups for all employees to connect in person and virtually
- Competitive Traditional & Roth 401k retirement plan with employer match
- Fitness center access in office building
- Opportunity to work in a fast-paced and dynamic environment
- Supportive and collaborative team culture
- Training and development opportunities to help you grow your skills
Ready to Join Our Team?
If you are a highly motivated and results-oriented individual with a passion for building relationships and helping businesses succeed, we encourage you to apply!
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Who's Hiring



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.
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