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 Executive Customer Advisor to join our Services team reporting to the Sr. Director, Gainsight Advisory Services. This role is a remote role based in the United States.

In this role, you’ll play a key role in helping customers unlock the full value of their customer experience (CX) strategy by partnering with both prospective and existing organizations to identify impactful use cases, deliver value assessments, and advise on high-leverage opportunities using Gainsight. You will engage directly with executive C-suite stakeholders, aligning CX initiatives to strategic business priorities, articulating measurable ROI, and serving as a trusted advisor to drive executive sponsorship, cross-functional alignment, and long-term value realization.This is a great opportunity for someone who thrives in a strategic, highly consultative environment and enjoys working cross-functionally with Sales, Customer Success, and Product teams. The ideal candidate brings strong skills in outcome-based consulting, modern customer success practices, and change management.

What You'll Do:

Strategic Customer Engagement (70%)

Partner with customers to understand their goals, identify high-impact use cases, and articulate a strategic path to realizing value through Gainsight solutions.
Advise customer executives and success leaders on how to optimize their CS strategy for long-term success by leveraging the latest practices and innovative approaches.
Develop and deliver strategic consulting engagements that enhance customer experience (CX) strategies, actively engage cross-functional stakeholders, and equip teams to maximize the value of Gainsight solutions.
Exhibit strong project management skills to manage multiple customer engagements simultaneously while ensuring timely and effective delivery.
Lead workshops, innovation sessions, and roundtables with stakeholders to develop a roadmap of strategic workflows, define performance benchmarks, and document value realization goals.

Value Realization & Adoption (15%)

Deliver tailored value assessments, maturity reviews, and business cases aligned with customer priorities.
Define baseline benchmarks and measurable KPIs to ensure alignment across the customer’s journey toward impact with Gainsight.
Post-deployment, track, analyze, and benchmark value realization progress through customer performance reviews and optimization sessions.
Drive value alignment across multiple products or solution areas. Ensure cohesive narratives, connected use cases, and unified measurement of outcomes that reflect the customer’s broader business objectives.

Internal Collaboration & Enablement (15%)

Collaborate effectively with internal teams (sales, product, marketing, professional services, etc) to share insights and enhance customer offerings.
Contribute to the development of repeatable frameworks, playbooks, and case studies to support customer-facing teams (i.e. QBRs, webinars, key insight slides) and that reinforce value realization efforts.
Continuously refine and evolve our value analysis tooling to ensure teams are equipped with the latest methodologies and insights for driving consistent, high-impact customer value narratives.
Share best practices, insights, and tools to support scalable customer engagement and internal enablement.
Proactively seek feedback and explore opportunities for enhancing customer experiences and internal processes.

Travel Expectations

1 Customer-facing Onsite Monthly
1 Planning offsite Quarterly

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 occasional travel for team meetings, training, or company events.

What We're Looking For:

Experience & Domain Expertise

7+ years of experience in customer success and/or strategic consulting with a proven record of driving customer value and outcomes.
2+ years of leadership experience in customer success.
Significant leadership experience in customer success roles, demonstrating the ability to guide teams and influence cross-functional initiatives that drive retention and growth.
Proven experience leading research, analysis, and presentation of insights derived from customer learnings to inform strategies and drive improvements.
Domain expertise in one or more key functions of customer experience (e.g., customer support, onboarding, customer engagement, retention strategy) to provide tailored guidance and best practices to clients.
Communication & Presentation Skills:
- Exceptional verbal and written communication skills, with demonstrated ability to deliver engaging presentations and articulate complex concepts to diverse audiences, including C-suite executives.
- Experience facilitating large working sessions and workshops with diverse stakeholders, fostering collaboration and ensuring productive discussions.
Analytical Skills:
- Strong analytical and problem-solving skills, with the ability to interpret data and develop actionable recommendations.
Interpersonal Skills:
- Excellent relationship-building skills with a customer-centric mindset, enabling effective engagement with stakeholders at various organizational levels.
- Ability to challenge customers on the status quo, encouraging them to adopt innovative approaches while advocating for their 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 $140,000 – $155,000 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 beingHuman-First. Learn morehere.

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 themhere!

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.

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Executive Customer Advisor