Gainsight CS Operations Analyst

Lwolf; Toronto; On-site; CAD 85,000 - 135,000; Full time

Job summary

Lone Wolf Technologies seeks an experienced Gainsight Administration / Operations expert to own the platform and build the operational foundation for our future-state Customer Success model. Reporting to the Vice President of Customer Success, this hands-on role requires deep Gainsight CS expertise, Journey Orchestrator mastery, and the ability to translate business requirements into scalable workflows.

Configure Gainsight CS, PX, and Skilljar, build automated journeys, and develop rules, health

Qualifications

• 3+ years of hands-on Gainsight administration in a production environment.
• Experience building a Gainsight implementation, not just end-user usage.
• Deep hands-on Journey Orchestrator experience with multi-step journeys and triggers.
• Strong experience with Rules Engine, Health/Scorecards, Playbooks, and dashboards.
• Experience with Salesforce CRM data models, accounts, and integrations.
• Ability to translate business requirements into scalable technical configurations.
• Strong troubleshooting, analytical, and data-management skills.
• Understanding of CS workflows like onboarding, adoption, and retention.

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 with audiences, triggers, and automated communications.
• Translate customer journey strategies into scalable Gainsight workflows with CS leadership.
• Manage Rules Engine configurations, data transformations, and reporting logic.
• Integrate and operationalize customer data within Gainsight with other system owners.
• Support Gainsight PX and Skilljar for digital adoption and education motions.
• Establish governance, documentation, testing, change management, and administration standards.
• Train and enable CS users while improving workflows and reducing friction.

Skills

Gainsight admin

Journey Orchestrator

Rules Engine

Reports & Dashboards

Salesforce integration

Data transformations

Tools

Gainsight CS

Gainsight PX

Skilljar

Salesforce

Job description

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.

• 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.

• 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.

Preferred Qualifications

• 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.