Remote Principal Customer Success Manager

We’re building the AI-driven future of customer success, from retention to growth! 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 Principal Customer Success Manager to join the Customer Success team reporting to the Director, Customer Success. This role is a remote role based in the United States. In this role, you'll play a key role in driving retention, expansion, and advocacy across Gainsight's Strategic Accounts segment by leading executive-level client partnerships, proactively mitigating strategic risks, and quantifying ROI throughout the customer lifecycle. This is a great opportunity for someone who thrives in a senior, ambiguity-heavy environment and enjoys working cross-functionally with teams like Sales, Product, Marketing, and Services. The ideal candidate brings strong skills in strategic account management, C-level relationship building, and data-driven executive communication. What You'll Do: Develop and lead strategic client partnerships to drive transformative outcomes and exceptional experiences for both client organizations and their customers. Quantify, deliver, and strategically communicate ROI for clients throughout their lifecycle, demonstrating significant business impact and value creation. Act as a trusted advisor and thought leader on advanced use cases and Customer Success industry best practices, thereby influencing industry trends and client strategies. Cultivate deep executive-level relationships within client organizations, proactively identifying and mitigating strategic risks while championing an unparalleled end-to-end customer journey. Architect and deliver high-impact customer deliverables, including presentations, strategic process innovations, and executive-level strategy recommendations that directly align with and advance senior executive priorities and goals. Leverage Gainsight technology to establish and track sophisticated client goals, objectives, and success metrics, driving alignment and accountability for shared success. Drive cross-functional initiatives within Gainsight to identify strategic opportunities and risks and to develop and present comprehensive innovative solutions to clients. Serve as a primary source of strategic intelligence on client business needs, providing actionable insights that influence internal strategy and leadership decisions. Collaborate strategically with Account Executives to identify and capitalize on significant cross-sell and upsell opportunities, ensuring seamless renewals and maximizing client value. Represent Gainsight as a recognized industry expert and thought leader in customer interactions, high-profile industry and corporate events, and online communities, thereby enhancing Gainsight's brand influence. 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 may require occasional travel for team meetings, training, customer meetings or company events. What We're Looking For: Over 10 years of progressive experience in Customer Success, with a proven record of managing strategic accounts and driving significant business outcomes. Minimum of 3 years of experience managing >$1M ARR account(s) Expert-level knowledge of Customer Success best practices, including advanced retention, expansion, adoption, and advocacy strategies. Skilled in mentoring and coaching others on these practices. Extensive experience with highly complex, enterprise-level products, showcasing a deep understanding of technical solutions and the ability to articulate their value to executive stakeholders. Prefers C-level engagement, with a proven ability to build and maintain strong relationships, translate intricate executive priorities into actionable strategic initiatives, and drive measurable ROI at scale. Exceptional skill in navigating and leading through ambiguity, designing and implementing scalable processes, driving strategic decision-making, and effectively managing crisis situations with composure and decisiveness. Proven leadership in cross-functional collaboration, fostering alignment across Sales, Product, Marketing, and Services to achieve optimal customer outcomes and strategic business objectives. Demonstrated thought leadership in the Customer Success industry, contributing to industry events, publications, or communities, and influencing best practices. Experienced in developing and delivering executive-level presentations and strategic recommendations, supported by data-driven insights and a deep understanding of client business needs. 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 $150,000 -$175,000 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 contact View email address on click.appcast.io . 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.