Customer Success Operations & Insights Lead (AI)

TL;DR

Customer Success Operations & Insights Lead (AI/Analytics): Developing and managing the client success technology ecosystem and reporting frameworks with an accent on Gainsight administration and AI-driven operational efficiency. Focus on designing customer health models, automating CSM workflows, and synthesizing complex data into executive-level narratives.

Location: Chicago, Illinois, USA

Salary: $131,750 - $155,000

Company

A global leader in commercial real estate services and investment management.

What you will do

• Administer and optimize the Client Success technology ecosystem, focusing on Gainsight and Smartsheet.
• Design customer health models, success frameworks, and automated workflows to proactively manage client risk.
• Deploy AI-driven capabilities such as predictive health signals and sentiment analysis to increase CSM efficiency.
• Synthesize quantitative and qualitative data into executive-ready reporting packages and board-level narratives.
• Establish data governance standards across CRM, billing, product usage, and client feedback sources.
• Lead the adoption of AI enhancements through training, documentation, and cross-functional enablement.

Requirements

• Experience administering Client Success platforms like Gainsight, Totango, ClientSuccess, or Planhat.
• Proficiency with CRM and service tools such as Salesforce and Zendesk.
• Ability to translate complex business requirements into system designs, data models, and dashboards.
• Strong analytical and storytelling skills to create executive-level insights.
• Demonstrated expertise in Microsoft PowerPoint and intermediate experience with Smartsheet.
• Must be based in Chicago, Illinois, USA

Culture & Benefits

• Comprehensive health, vision, and dental insurance.
• Flexible spending accounts (FSA) and health savings accounts (HSA).
• Retirement savings plans.
• Life and disability insurance programs.
• Paid and unpaid time away from work.