Director, Customer Success Operations - Remote Eligible

Director, CS 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.

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:

1. 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.
2. Design and operationalize scalable customer journeys across onboarding, adoption, renewal, and expansion.
3. Own CS operational strategy including financial planning, forecasting (GRR, NRR, churn), and capacity modeling.
4. Own the CS compensation plan design in alignment with strategic priorities to optimize retention and CS performance.
5. Lead strategic transformation programs and organizational change initiatives.
6. Own retention forecasting models and customer health scoring frameworks.
7. Develop predictive models and segmentation strategies that optimize customer outcomes.
8. Create executive dashboards and reporting for CS performance metrics.
9. Drive advanced analytics using BI platforms (Sigma), and Gainsight's native capabilities to deliver executive insights.
10. Lead Gainsight platform optimization including automation, playbooks, and AI-powered workflows.
11. Evaluate and deploy AI tools that enhance CSM productivity and deliver proactive customer insights.
12. Champion process automation and data governance excellence across CS operations.
13. Drive innovation in customer journey design and lifecycle management.
14. Lead and mentor high-performing CS Operations team, fostering culture of innovation, accountability, growth, and impact.
15. Partner across Sales, Product, Marketing, Professional Services, Finance, and Support to align customer initiatives.
16. Manage executive communications, business reviews, and board-level CS reporting.

What We're Looking For:

• 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, and a shared focus on solving real-world problems. With a growing suite of products across customer success, product experience, community, education, and AI-powered relationship intelligence, we continue to evolve with the needs of our customers. When people with diverse strengths, a strong sense of community, and true passion for our mission come together, they drive greater impact and create lasting value. What underpins it all is a culture that offers the stability, trust, and support that people need - not just to do the job, but to show up as themselves and feel connected to the work they do. Gainsters love working here for several reasons.

Our Compensation and Benefits: At Gainsight, we believe great work happens when teammates feel fully supported. The starting base salary range for this role is $160,000-$195,000 USD annually. This role is also eligible for commission based on performance and participation in Gainsight's equity program. Actual compensation may vary based on factors such as skills, experience, and location. We offer a comprehensive benefits package including fully covered medical premiums (employee-only), flexible PTO, 401(k) plan, dental and vision coverage, and remote work options. Additional benefits include a $10,000 lifetime fertility stipend and access to coworking spaces around the globe. You'll also enjoy dedicated Recharge Holidays - one long weekend each quarter to relax and reset.

Our Core Values: We are guided by our values and our mission to be living proof you can win in business while being Human-First.

Our Growth Opportunities: From mentoring to career development opportunities, we're passionate about helping our teammates learn, grow, and thrive.

If this sounds like the right role for you, we'd love to hear from you.

Additional Information: We're committed to creating an inclusive, fair, and transparent hiring process. As an equal opportunity employer, we celebrate diversity and are committed to creating a welcoming experience for all candidates. If you require accommodations or have questions about how your personal data will be used during the hiring process, please let the recruiting team know. If you are based in San Francisco, we will consider qualified applicants with arrest and conviction records, in accordance with the San Francisco Fair Chance Ordinance.