Director, Customer Success Operations

We’re building the AI-driven future of customer success, from retention to growth!

Gainsight is the AI-powered retention engine behind the world’s most customer-centric companies. The Gainsight CustomerOS platform orchestrates the customer journey from onboarding to outcomes to advocacy. More than 2,000 companies trust Gainsight’s applications and AI agents to drive learning, adoption, community connection, and success for their customers. To explore how our suite of solutions is shaping the future of customer success, check out the link. 

About This Role:

We’re looking for a full-time Director, CS Operations to join our Sales team  reporting to the SVP, Revenue Operations. This role is a remote role based in the United States.

In this role, you’ll play a key role in shaping the future of Customer Success operations by leveraging Gainsight’s own platform to drive best practices, operational excellence, and innovation. This is a great opportunity for someone who thrives in a fast-moving, strategically impactful environment and enjoys working cross-functionally with teams like Product, Data, and Customer Success. The ideal candidate brings strong skills in systems-level thinking, operational execution, and harnessing AI to deliver predictive insights and scalable customer experiences.

What You'll Do: 

• Lead, design and implement a proactive customer engagement and go-to-market strategy that aligns with the CCO’s priorities and Gainsight’s growth objectives.

• Design and operationalize scalable customer journeys across onboarding, adoption, renewal, and expansion.

• Own CS operational strategy including financial planning, forecasting (GRR, NRR, churn), and capacity modeling.

• Own the CS compensation plan design in alignment with strategic priorities to optimize retention and CS performance. 

• Lead strategic transformation programs and organizational change initiatives.

• Own retention forecasting models and customer health scoring frameworks.

• Develop predictive models and segmentation strategies that optimize customer outcomes.

• Create executive dashboards and reporting for CS performance metrics.

• Drive advanced analytics using BI platforms (Sigma), and Gainsight's native capabilities to deliver executive insights.

• Lead Gainsight platform optimization including automation, playbooks, and AI-powered workflows.

• Evaluate and deploy AI tools that enhance CSM productivity and deliver proactive customer insights

• Champion process automation and data governance excellence across CS operations.

• Drive innovation in customer journey design and lifecycle management.

• Lead and mentor high-performing CS Operations team, fostering culture of innovation, accountability, growth, and impact. 

• Partner across Sales, Product, Marketing, Professional Services, Finance, and Support to align customer initiatives.

• Manage executive communications, business reviews, and board-level CS reporting.

This is not a complete list of responsibilities, and the scope of the role may evolve with the needs of the team and business.

What We're Looking For: 

Must-have skills or experience:

• 10+ years of experience in Customer Success Operations, Revenue Operations, GTM Strategy, or management consulting within high-growth B2B SaaS companies

• 8+ years of progressive leadership experience building and managing high-performing, cross-functional teams across strategy, analytics, and operations

• Demonstrated expertise with Gainsight platform including advanced configuration, automation, and analytics capabilities

• Strong proficiency in Salesforce, and BI platforms (Sigma, Tableau, Looker, Power BI) with ability to translate complex data into executive insights

• Experience with complementary CS tech stack including CPQ, Outreach, Gong, HubSpot, or similar platforms

• Proven track record leading strategic planning and transformation initiatives at scale in global, matrixed environments

Why You’ll Love It Here:

Gainsight is a place where innovation is shaped through collaboration, curiosity, an