Customer Success Operations & Insights Lead

Job Title

Customer Success Operations & Insights Lead

Job Description Summary

The Customer Success Operations & Insights Lead owns Gainsight administration, Smartsheet solution design and reporting, and the creation of executive-level client summary narratives. This role enables proactive customer health management, streamlined workflows, and board-ready insights that drive retention, expansion, and a world-class client experience.

Job Description

Client Success Technology, Data & AI Enablement

• Serve as administrator of the Client Success and Client Experience technology ecosystem, ensuring platforms are optimized to support customer health management, lifecycle visibility, and crossâ‘functional execution.
• Design and maintain customer health models, success frameworks, engagement workflows, and automated plays that proactively surface risk, opportunity, and value gaps.
• Identify and deploy AIâ‘driven capabilities (e.g., predictive health signals, sentiment analysis, intelligent alerts, summarization, and recommendations) to increase efficiency and reduce manual effort across CSM workflows.
• Establish governance standards for data quality, definitions, permissions, and integrations across CRM, support, billing, product usage, and client feedback sources.
• Translate product usage data, client interactions, and voiceâ‘ofâ‘theâ‘client inputs into unified client records and forwardâ‘looking insights.
• Lead change and release management for Client Success systems and AI enhancements, including testing, documentation, enablement, and communications.
• Partner with Client Success, Sales, Product, Operations, and RevOps leaders to align technology, data, and AI investments with retention, expansion, and client experience outcomes.

Process, Structure & Workflow Design

• Architect scalable Client Success operating models, workflows, and governance structures that support endâ‘toâ‘end client lifecycle management.
• Redesign processes to leverage automation and AI where appropriate, streamlining action planning, followâ‘ups, risk management, and reporting.
• Develop standardized templates, playbooks, and operating guides that balance consistency with flexibility by client segment or engagement type.
• Build intelligent workflows for intake, prioritization, approvals, progress tracking, and escalations tied to retention and client health.
• Create portfolioâ‘level rollups that provide leaders with clear visibility into client priorities, risks, value realization, and execution status.

Executiveâ‘Level Client Insights, Analytics & Reporting

• Produce concise, executiveâ‘ready client insights that synthesize quantitative data, qualitative feedback, and AIâ‘driven analysis into clear narratives on client sentiment, risk, engagement, and outcomes.
• Leverage AI to accelerate analysis of client interviews, surveys, transcripts, and feedbackâ”identifying themes, trends, and emerging risks at scale.
• Develop recurring executive and boardâ‘level reporting packages, including trend analysis, cohort views, benchmarks, and forwardâ‘looking insights.
• Create standardized storyframes (e.g., Objectives → Actions → Results → Risks → Next Best Actions) to ensure clarity, consistency, and decisionâ‘readiness.
• Establish reporting cadences and review workflows with Client Success, Sales, Product, and Leadership teams.
• Maintain a governed library of client case studies, outcomes, and referenceable insights with strong version control.

Crossâ‘Functional Enablement, Governance & AI Adoption

• Define and enforce standards for data inputs, tagging, health indicators, playbook compliance, and AIâ‘assisted workflows.
• Enable Client Success Managers and leaders through training, office hours, documentation, and best practicesâ”building confidence in using AI responsibly and effectively.
• Partner with Finance and RevOps to align definitions for revenue, retention, churn, expansion, and risk categorization.
• Manage intake, prioritization, and delivery of enhancements across systems, workflows, analytics, and AI capabilities, maintaining transparent roadmaps and backlogs.

What This Role Delivers

• Proactive, insightâ‘driven Client Success with earlier risk detection and clearer value realization.
• Increased efficiency and scalability through automation and AIâ‘enabled workflows.
• Executiveâ‘ready reporting that drives alignment, informed decisionâ‘making, and action.
• A futureâ‘ready foundation for worldâ‘class client experience, retention, and growth.

Qualifications & Experience

• Prior experience administering, configuring, or operating Client Success and/or Client Experience platforms, with a strong understanding of how these systems support retention, expansion, and client engagement at scale.
• Demonstrated experience with one or more industryâ‘leading platforms such as Gainsight, Totango, ClientSuccess, Client Share, Planhat, Salesforce, Zendesk, and/or Medallia, or comparable customer success, CRM, service, or voiceâ‘ofâ‘theâ‘customer tools.
• Ability to translate business requirements into system design, workflows, data models, dashboards, and executiveâ‘level reportingâ”regardless of platform.
• Experience working with integrated data environments (e.g., CRM, support, billing, usage, surveys) and applying analytics to inform customer health, risk, and opportunity.
• Strong analytical, synthesis, and storytelling skills, with the ability to distill complex data and client feedback into clear, executiveâ‘ready insights.
• Comfort leveraging automation and AIâ‘enabled capabilities to drive efficiency, consistency, and scale across Client Success and retention processes.
• Demonstrated expertise experience in MicroSoft PowerPoint.
• Intermediate level experience with SmartSheet.

Cushman & Wakefield also provides eligible employees with an opportunity to enroll in a variety of benefit programs, generally including health, vision, and dental insurance, flexible spending accounts, health savings accounts, retirement savings plans, life, and disability insurance programs, and paid and unpaid time away from work. In addition to a comprehensive benefits package, Cushman and Wakefield provide eligible employees with competitive pay, which may vary depending on eligibility factors such as geographic location, date of hire, total hours worked, job type, business line, and applicability of collective bargaining agreements. The compensation that will be offered to the successful candidate will depend on factors such as whether the position is covered by a collective bargaining agreement, the geographic area in which the work will be performed, market pay rates in that area, and the candidateâ™s experience and qualifications. The company will not pay less than minimum wage for this role. The compensation for the position is: $ 131,750.00 - $155,000.00

C&W Services is an Equal Opportunity employer to all protected groups, including protected veterans and individuals with disabilities.  Discrimination of any type will not be tolerated.

In compliance with the Americans with Disabilities Act Amendments Act (ADAAA), if you have a disability and would like to request an accommodation in order to apply for a position at C&W Services, please call the ADA line at 1-888-365-5406 or email . Please refer to the job title and job location when you contact us.

INCO: âœC&W Servicesâ