Sr Director, Digital Customer Success

Senior Director, Digital Customer Success

Gainsight is the 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.

We're looking for a full-time Senior Director, Digital Customer Success to join our Customer Success team reporting to the Chief Customer Officer. This role is a remote role based in the United States.

In this role, you'll play a key role in building and leading our digital-first engagement model, enabling scalable, tech-powered customer experiences across the full lifecycle and across our entire customer operating system. This role spans the entire post-sale customer journey, overseeing both strategy and execution across five major domains : Digital Customer Success and Tech-Touch Programs, Community and Education Strategy, Product Experience, AI and Agentic Customer Engagement, and Support Collaboration and Deflection Efficiency.

This is a rare opportunity for a senior operator and strategist to lead a modern, data-driven, and AI-augmented approach to Customer Success. You'll partner deeply with Product, Support, Education, RevOps, and Marketing to execute a unified digital motion.

What You'll Do :

• Build a unified digital CS strategy that scales across all segments and products driving efficiency, retention, and product adoption through digital channels.
• Design and operationalize tech-touch and hybrid engagement models including digital success planning and lifecycle-based journey orchestration.
• Embed automation and AI into the customer journey from onboarding flows and stakeholder alerts to in-app engagement and intelligent nudges.
• Own the digital engagement tech stack, including Gainsight, PX, AI copilots / agents, knowledge systems, community platforms, and LMS tools.
• Drive community-led success by integrating digital CS with our customer community and education functions supporting peer learning, events, and enablement at scale.
• Collaborate with Support on agentic strategies, chatbot design, and proactive deflection methods to reduce case volume and improve self-service rates.
• Define and manage a KPI framework that demonstrates the impact of digital success programs on retention, NRR, product usage, and cost-to-serve.
• Lead a high-performing team of digital CS managers, program owners, and cross-functional partners to deliver outcomes at scale.
• Drive change management efforts by navigating organizational shifts and executing strategic transformation initiatives across entire Customer Success organization, not limited to digital strategies.
• Develop and mentor leadership talent within the GTM team, with a focus on growing future managers and strengthening organizational depth.
• Actively engage with Executive Leadership team to align and advance company-wide Digital Customer Success priorities, including product innovation and prioritization.

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 :

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.

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. Learn more.

Our Growth Opportunities :

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

Our Parody Videos :

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