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, Customer Success to join our Customer Success team reporting to the VP, Customer Success. This role is a remote role based in The United States.

In this role, you’ll play a key role in driving growth, retention, and long-term value across our highest-value customers by leading and scaling our Strategic CSM team and ensuring clients fully realize the impact of our solutions. This is a great opportunity for someone who thrives in a fast-paced, growth-oriented environment and enjoys working cross-functionally with teams like Sales, Product, and Support. The ideal candidate brings strong skills in customer success leadership, commercial acumen, and strategic, data-driven decision-making.

What You'll Do:

• Strategic Vision & Flexibility: Develop and communicate a customer success strategy that aligns with evolving GTM strategies and company objectives. Adapt this strategy to address shifting customer needs and internal changes, ensuring consistent success outcomes.

• Lead, Mentor, and Scale: Manage and inspire a team of Customer Success Managers focused on Gainsight’s largest accounts, driving exceptional and consistent process, value realization, and client success, even through periods of change.

• Innovation: Bring new ways of leveraging technology (AI and automation) to influence team effectiveness and customer value.

• Data-Driven Insights: Establish and monitor key metrics and performance indicators (KPIs) to assess customer health, team performance, and product adoption. Understand underlying CS metrics (e.g., CAC, LTV, NRR) to focus on efficient growth and recommend strategic investment asks as part of annual planning.

• Consultative Approach: Provide consultative guidance to customers, helping them leverage the Gainsight platform to meet their goals. Lead the team in offering technical support, ensuring customers can optimize their use of the Gainsight platform and resolve any challenges quickly.

• Navigate Ambiguity: Demonstrate the ability to work through levels of ambiguity as the company transitions through GTM changes. Maintain focus on customer outcomes, ensuring that changes in internal strategy do not disrupt the customer experience.

• Cross-Functional Collaboration: Work closely with Sales, Product, Marketing, and Support teams to ensure seamless customer journeys, from onboarding to adoption, and to resolve any customer challenges swiftly and effectively. Drive alignment between these teams during GTM transitions.

• Demand Excellence: Cultivate a culture of collaboration, learning, and excellence within the Customer Success team. Drive accountability and provide ongoing coaching, mentoring, and professional development to build a high-performing, customer-centric team.

• Escalations: Serve as a trusted advisor to our most strategic enterprise customers, proactively addressing their challenges, both consultative and technical, and aligning their success with Gainsight’s solutions.

• Industry Leadership: Stay current with customer success best practices, industry trends, and evolving customer needs. Use this knowledge to innovate and develop the Customer Success function, including optimizing the Gainsight platform to serve our enterprise customers better.

This is not a complete list of responsibilities, and the scope of the role may evolve with the needs of the team and business. This role will require 25%+ travel for team meetings, customer meetings, training, or company events.

What We're Looking For:

• 8+ years of experience in customer success, account management, or related fields, with at least 5 years in a leadership role managing and developing high-performing teams, including Senior CSMs or Enterprise Success Leaders.

• Proven experience working with global customers, demonstrating an ability to understand their complex business needs and challenges and aligning them with solutions that deliver measurable outcomes.

• Proven ability to coach and develop senior-level talent, specifically Senior CSMs and Enterprise Success Leaders, to improve their performance, strategic thinking, and ability to manage complex relationships.

• Demonstrated ability to navigate ambiguity and adapt to changing strategies, particularly in GTM transformations.

• Track record of success in driving customer retention, satisfaction, and expansion in a B2B SaaS environment, with experience leading strategic enterprise-level engagements.

• Strong analytical skills, with the ability to use data to guide decision-making and drive continuous improvement initiatives

• Possess a cross-functional mindset, with the ability to build executive-level relationships and influence stakeholders across various levels.

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 $178,400 – $195,000 USD annually. Actual compensation may vary based on factors such as skills, experience, and location. In addition to base pay, this role is eligible for an annual bonus and participation in Gainsight’s equity program.

• 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!

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.