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Customer Success Operations & Insights Lead

April 30, 2026

<h1>Job Title</h1>Customer Success Operations & Insights Lead<h1>Job Description Summary</h1>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.<h1>Job Description</h1>Key ResponsibilitiesGainsight Administration 35% of time<ul><li>Serve as platform owner for Gainsight (CS + PX where applicable): user management, permissions, data governance, and integrations (CRM, support, billing).</li><li>Design and maintain health scores, playbooks, journeys, CTAs, Success Plans, and automated outreaches.</li><li>Build and optimize dashboards for CSMs, leadership, and cross-functional partners; manage data quality SLAs.</li><li>Partner with Client Success Leadership, SalesForce Support, and Client Services to align product telemetry, usage data, and customer feedback into Gainsight objects.</li><li>Own release management: sandbox testing, documentation, enablement, and change communications.</li></ul>Smartsheet Solution Design & Reporting 20% of time<ul><li>Architect Smartsheet workspaces, sheets, and Control Center blueprints for scalable project/portfolio management.</li><li>Develop automated workflows: forms, update requests, reminders, alerts, and approvals.</li><li>Create portfolio rollups, executive dashboards, and cross-sheet reporting; establish naming conventions and metadata standards.</li><li>Integrate Smartsheet with source systems (CRM, data warehouse, ticketing) via Data Shuttle/Connectors; maintain refresh cadences.</li><li>Document templates and operating guides; train users and manage permissions.</li><li>Project Manage Action Plans as needed</li></ul>Executive-Level Client Summary & Insights 45% of Time<ul><li>Produce detailed, concise, executive-ready client reports distilling client perception, voice of the client, risk, sentiment, and relationship engagement.</li><li>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.</li><li>Develop quarterly/board-report packs with trend analyses, cohort views, benchmarks, and narrative themes. Quarterly report details will</li><li>Create standardized storyframes: Objectives → Actions → Results → Next Best Actions; tailor to executive audience.</li><li>Establish publication cadences (monthly/quarterly) and a review workflow with CSMs, Sales, and Product.</li><li>Maintain a library of client case studies and referenceable outcomes; manage version control.</li></ul>Cross-Functional Enablement & Governance<ul><li>Define operating standards for data quality, tagging, health score inputs, and playbook compliance.</li><li>Run office hours, training, and enablement for CSMs and leaders; maintain knowledge base content.</li><li>Partner with Finance and RevOps to align definitions of ARR, churn, risk categories, and expansion metrics.</li><li>Manage intake and prioritization of enhancements; maintain a transparent roadmap and backlog.</li></ul> 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 candidate’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 - $155,000.00C&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 <a href="mailto:Accommodations@cushwake.com?subject=Accommodations" target="_blank" rel="noopener noreferrer">Accommodations@cushwake.com</a>. Please refer to the job title and job location when you contact us.INCO: “C&W Services”

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...