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.
• This is a remote position, but you must be located within the Central or East Coast region.

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Key Responsibilities

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Gainsight Administration 35% of time

• Serve as platform owner for Gainsight (CS + PX where applicable): user management, permissions, data governance, and integrations (CRM, support, billing).
• Design and maintain health scores, playbooks, journeys, CTAs, Success Plans, and automated outreaches.
• Build and optimize dashboards for CSMs, leadership, and cross-functional partners; manage data quality SLAs.
• Partner with Client Success Leadership, SalesForce Support, and Client Services to align product telemetry, usage data, and customer feedback into Gainsight objects.
• Own release management: sandbox testing, documentation, enablement, and change communications.

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Smartsheet Solution Design & Reporting 20% of time

• Architect Smartsheet workspaces, sheets, and Control Center blueprints for scalable project/portfolio management.
• Develop automated workflows: forms, update requests, reminders, alerts, and approvals.
• Create portfolio rollups, executive dashboards, and cross-sheet reporting; establish naming conventions and metadata standards.
• Integrate Smartsheet with source systems (CRM, data warehouse, ticketing) via Data Shuttle/Connectors; maintain refresh cadences.
• Document templates and operating guides; train users and manage permissions.
• Project Manage Action Plans as needed

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Executive-Level Client Summary & Insights 45% of Time

• Produce detailed, concise, executive-ready client reports distilling client perception, voice of the client, risk, sentiment, and relationship engagement.
• These summaries are full written reports derived from client interview transcripts, requiring synthesis of qualitative insights into clear, actionable narratives tailored for executive audiences. Client Success leadership will partner for report details to be written.
• Develop quarterly/board-report packs with trend analyses, cohort views, benchmarks, and narrative themes. Quarterly report details will
• Create standardized storyframes: Objectives → Actions → Results → Next Best Actions; tailor to executive audience.
• Establish publication cadences (monthly/quarterly) and a review workflow with CSMs, Sales, and Product.
• Maintain a library of client case studies and referenceable outcomes; manage version control.

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Cross-Functional Enablement & Governance

• Define operating standards for data quality, tagging, health score inputs, and playbook compliance.
• Run office hours, training, and enablement for CSMs and leaders; maintain knowledge base content.
• Partner with Finance and RevOps to align definitions of ARR, churn, risk categories, and expansion metrics.
• Manage intake and prioritization of enhancements; maintain a transparent roadmap and backlog.