Customer Success Manager Jobs in Chicago, IL

Entry‑level CSMs earn between $70,000 and $90,000 annually. Mid‑level managers earn $90,000 to $120,000. Senior CSMs with 5+ years of experience can command $120,000 to $160,000, while CS leads or directors often exceed $180,000, especially in high‑growth tech firms and in markets like the Bay Area.

Key skills include customer relationship management, data analysis, product expertise, and communication. Certifications such as Gainsight Certified Customer Success Manager, Salesforce Certified Service Cloud Consultant, Zendesk Certified Support Specialist, and HubSpot CS certifications give a competitive edge.

More than 80% of openings allow full‑time remote or hybrid arrangements. Companies use tools like Gainsight, Teams, and Zoom to maintain collaboration across distributed teams.

A typical trajectory moves from Junior CSM to Senior CSM, then to CS Lead or Manager, followed by Director of Customer Success, and ultimately VP or Head of Customer Success. Each step adds responsibility for strategy, team leadership, and cross‑functional coordination.

Current trends include AI‑driven customer analytics, automated health scoring, subscription‑based revenue models, and the rise of CS Ops teams that focus on process optimization and data governance. CS managers are increasingly partnering with product and engineering to embed customer insights into development cycles.