Sr Director, Digital Customer Success

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 Senior Director, Digital CS 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: 

• 10+ years of experience in CS, digital programs, or scaled operations roles in B2B SaaS

• Proven track record leading large-scale digital CS transformations (ideally across multiple segments)

• Familiarity with AI tooling, journey orchestration, and agentic models in CS

• Strong understanding of community-led growth, customer education, and LMS strategies

• Experience with metrics-based storytelling and reporting to senior leadership

• A builder mindset where you bring structure, speed, and clarity to ambiguous problems

• A strong sense of ownership and urgency; you’re outcome-oriented and scrappy

• Maintain the ability to travel 10-15% of the time.

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. Here are a few:

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 $154,000-$200,200 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. Learn more here.

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

Our Parody Videos: No explanation needed. Just watch them here!

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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 contact [email protected]. 

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.