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.

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.

• 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.

• 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‑leve…