Customer Success Specialist Jobs in Chicago, IL
Customer Success Specialist jobs in Chicago are concentrated in the Loop, River North, and the Fulton Market tech corridor, with strong demand from SaaS, fintech, and healthcare technology employers. Companies hiring right now include Salesforce, Okta, and Uber. See the openings below and apply to the ones that match your experience.
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The Role:
ThoughtSpot is redefining business intelligence through AI-driven insights, and Customer Success is at the heart of that transformation. As a Senior Manager of Customer Success, you’ll lead a high-performing team of CSMs focused on driving adoption, measurable value, and net revenue retention across our enterprise customer base.
You’ll be a strategic operator and team builder, responsible for scaling systems, developing talent, and collaborating cross-functionally to drive customer outcomes and company growth. This role reports to the Director of Customer Success and partners closely with Sales, Product, CS Architects, and Operations.
Location(s): Chicago or Mountain View
What You'll Do:
Team Leadership & Coaching
- Lead and grow a team of CSMs focused on adoption, retention, and expansion.
- Define success metrics, manage performance, and support career development.
- Serve as a strategic escalation point for your team and customer portfolio.
Customer Outcomes & Revenue Growth
- Drive NRR through proactive value realization and expansion strategies.
- Partner with Sales to co-develop account strategies and surface growth opportunities.
- Equip CSMs to navigate complex customer orgs and influence renewals and upsells.
Operational Excellence
- Own team KPIs and lead regular inspection rhythms to track performance.
- Identify inefficiencies and work with CS Ops to scale processes and systems.
- Leverage tools and data to drive consistency, predictability, and customer health.
Cross-Functional Collaboration
- Align closely with Product, Sales, and Support to represent the voice of the customer.
- Influence internal roadmaps and drive a seamless post-sale customer experience.
- Act as a strategic partner to internal leaders, surfacing insights and solutions.
Strategic Problem Solving
- Guide the team through complex issues, customer risks, and escalations.
- Enable structured thinking, proactive risk mitigation, and creative solutions.
- Foster a culture of continuous learning, feedback, and adaptability.
What You Bring:
- 2+ years managing Customer Success or post-sale teams; 5+ years in enterprise SaaS CS or AM roles
- Proven success driving NRR, adoption, and strategic account growth.
- Strong coaching, team development, and performance management experience.
- Operational rigor with data fluency and experience optimizing CS processes.
- Skilled in cross-functional collaboration, customer advocacy, and executive communication
- Growth mindset with a passion for learning, iteration, and leading through change.
Hybrid Work at ThoughtSpot
Spotters are expected in-office 3 days per week to experience the energy of their local office. This approach balances the benefits of in-person collaboration and peer learning with the flexibility needed by individuals and teams.
About ThoughtSpot
The world’s most innovative companies turn to ThoughtSpot’s AI-Powered Analytics to put data in the hands of everyone, from the C-suite to the frontline. With simple, natural language search and AI, anyone can ask questions, discover insights, and act with confidence. Unlike legacy tools that sacrifice performance for complexity, ThoughtSpot is intuitively designed for every business user while being built to handle the most complex, large-scale data, wherever it resides. This unique combination of speed and simplicity is why enterprise leaders trust ThoughtSpot to transform decision-making into a truly data-driven culture.
At ThoughtSpot, we’re a curious, data-driven bunch. We believe the world works better when everyone has access to facts. That’s why we build products that make asking and answering data questions as natural as having a conversation.
Mandatory and Required Skills for All ThoughtSpot Roles
Spotters are expected to demonstrate AI literacy and workflow integration to include the ability to:
- Comfortably and confidently integrate artificial intelligence into their daily workflow to increase productivity and quality.
- Hands-on experience to leverage AI tools (industry-leading LLMs) to increase productivity, automate routine tasks, and improve work quality.
- Speak to the experience of using AI for research, content creation, and document summarization while maintaining ownership of judgment and final decisions.
- Write effective prompts to get the most accurate and creative results from AI tools.
Spotters are expected to exemplify these key traits and AI Mindset:
- Curiosity in exploring new AI tools
- Adaptability to quickly learn and implement new, emerging AI technologies
- Critical thinking to know when to identify when AI should be used versus when human judgment is necessary
This combination of curiosity, adaptability, and discernment defines the AI mindset, and it’s required for every role at ThoughtSpot.
AI Mindset for All Spotters
At ThoughtSpot, we believe AI is a necessary and essential part of how we work. Every role, across every team, is expected to be fluent and comfortable with using AI to do their best work.
All Spotters are expected to experiment with ThoughtSpot’s AI tools (like Spotter and SpotterViz) and leading industry LLMs to streamline workflows, enhance output, and uncover new insights. Whether drafting content, analyzing data, or summarizing documents, AI is a daily partner. We value curiosity, openness to learning, and thoughtful application of AI to create real value. Training and resources are provided so every Spotter can confidently create with AI.
ThoughtSpot for All
At ThoughtSpot, diverse teams build better products. Complex data problems need many perspectives, not just one. We welcome different backgrounds, identities, and experiences, and we work to create a place where everyone can be themselves and do their best work. If this role excites you and you believe you’re a strong match, we encourage you to apply.
What Makes ThoughtSpot a Great Place to Work?
ThoughtSpot is the Agentic Analytics Platform that empowers every enterprise to transform insights into action, on a mission to make the world more fact-driven. We hire people with unique identities, backgrounds, and perspectives - this balance-for-the-better philosophy is key to our success. When paired with our culture of Trust, Customer Obsession, Innovation, and Intensity, ThoughtSpot cultivates a respectful culture that pushes norms to create world-class products. If you’re excited by the opportunity to work with some of the brightest minds in the business and make your mark on a truly innovative company, we invite you to read more about our mission and apply to the role that’s right for you.
The pay range for this role is:
147,420 - 210,600 USD per year (US US Zone 2)
See All 57 Customer Success Specialist Jobs in Chicago
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Find JobsCustomer Success Specialist Job Market in Chicago
Who's Hiring
- Salesforce3

- Okta2

- Uber2

- Adobe2

- Front2

Top Industries Hiring
- Technology & Software33
- Marketing & Advertising2
- Banking & Financial Services2
- Biotechnology & Pharmaceuticals2
- Energy1
Customer Success Specialist Jobs in Chicago: Frequently Asked Questions
How do I get a customer success specialist job in Chicago?
Focus your search on Chicago's SaaS and cloud software companies clustered in Fulton Market and the Loop, along with fintech firms in the West Loop and health tech employers on the Near North Side. Candidates who demonstrate experience with CRM platforms, churn analysis, and cross-functional account management stand out. Networking through Chicago-area tech meetups and industry events also gives local applicants a clear edge over remote-only applicants.
Which companies hire customer success specialists in Chicago?
Chicago customer success specialist roles are posted by Salesforce, Okta, and Uber and others right now, based on current listings on Migrate Mate as of June 2026. Chicago's hiring base is especially deep among mid-market SaaS platforms, financial technology firms, and enterprise healthcare software companies with regional headquarters or large offices in the city.
Are there remote customer success specialist jobs in Chicago?
Yes, customer success specialist work is generally well-suited to remote arrangements because the role centers on digital communication, CRM workflows, and account reviews rather than on-site tasks. About 64% of customer success specialist openings tied to Chicago are remote or hybrid as of June 2026, reflecting how broadly Chicago's tech and SaaS employers have embraced flexible work. Onboarding and quarterly business reviews are the functions most likely to require occasional in-office attendance.
How can I get a customer success specialist job in Chicago with little or no experience?
The most realistic entry path in Chicago is targeting customer support or account coordinator roles at mid-size SaaS or fintech companies, particularly those in Fulton Market and the West Loop that promote from within. Chicago employers at this stage value demonstrated comfort with tools like Salesforce or HubSpot, even from coursework or personal projects. Lateral moves from inside sales, technical support, or client-facing operations roles at local companies are also common entry points into dedicated customer success teams.
Which industries hire the most customer success specialists in Chicago?
The sectors hiring the most customer success specialists in Chicago are Technology & Software, Marketing & Advertising, and Banking & Financial Services, based on current listings on Migrate Mate as of June 2026. Chicago's role as a national hub for enterprise software, financial services technology, and healthcare IT means these industries maintain deep, consistent demand for customer success talent year-round.
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