Gainsight CS Operations Analyst

About the Position

Gainsight CS Operations Analyst

Location: Toronto, ON (Remote)

Employment Type: Full-time

Remote: Yes

Lone Wolf Technologies is transforming how we deliver Customer Success across a large and diverse customer base. As part of that transformation, we are implementing Gainsight CS, PX, and Skilljar to strengthen customer health management, digital engagement, adoption, and retention.

We are seeking an experienced Gainsight Administration / Operations expert to serve as the technical owner of the platform who will build the operational foundation for our future-state Customer Success model.

Reporting to the Vice President of Customer Success, this is a hands-on role for someone who has previously built, configured, and managed Gainsight in a complex SaaS environment. The ideal candidate brings deep technical expertise in Gainsight CS, strong Journey Orchestrator experience, and the ability to translate business requirements into scalable workflows, automation, reporting, and customer journeys.

Responsibilities

• Serve as the primary administrator and technical owner of Gainsight CS.
• Configure and maintain Gainsight objects, fields, layouts, permissions, health scores, CTAs, playbooks, Success Plans, reports, dashboards, and automation.
• Build and manage Journey Orchestrator programs, including audience criteria, branching logic, triggers, and automated communications.
• Partner with Customer Success leadership to translate customer journey and lifecycle strategies into scalable Gainsight workflows.
• Build and maintain Rules Engine configurations, data transformations, reporting logic, and automated customer health and risk signals.
• Partner with other system owners to integrate and operationalize customer data within Gainsight.
• Support the integration and use of Gainsight PX and Skilljar as part of broader digital adoption and customer education motions.
• Establish platform governance, documentation, testing, change management, and administration standards.
• Train and enable Customer Success users while continuously improving workflows and reducing administrative friction.

Requirements

• 3+ years of hands-on Gainsight administration experience in a production environment.
• Demonstrated experience building a Gainsight implementation, not simply using Gainsight as an end user.
• Deep hands-on experience with Journey Orchestrator, including building multi-step automated journeys, participant logic, and triggers.
• Strong experience with Rules Engine, Customer Health / Scorecards, Playbooks, Success Plans, Reports and Dashboards.
• Experience working with Salesforce and understanding CRM data models, account structures, and integrations.
• Experience translating business requirements into scalable technical configurations.
• Strong troubleshooting, analytical, and data-management skills.
• Strong understanding of Customer Success workflows such as onboarding, adoption, risk management, retention, and lifecycle engagement.

Nice to Have

• Gainsight Administrator certification or equivalent demonstrated expertise.
• Experience with Gainsight PX and Skilljar.
• Experience in a multi-product SaaS environment.
• Familiarity with SaaS metrics including ARR, GRR, NRR, churn, contraction, and product adoption.

We Offer

• Salary: $105,000 a year
• Work Environment: Remote
• Company: Lone Wolf Technologies

About the Company

Lone Wolf Technologies is committed to leveraging artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.

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