Gainsight

Role Description We’re looking for a full-time or part-time Customer Advisor to join our Services team reporting to the Senior 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 potential of our solutions by delivering strategic guidance, value assessments, and outcome-driven recommendations that advance their customer experience (CX) strategy. This is a great opportunity for someone who thrives in a highly consultative, fast-evolving environment and enjoys working cross-functionally with prospective and existing customers, customer success, and leadership teams. The ideal candidate brings strong skills in customer success strategy, change management, and outcome-based consulting. 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 Qualifications - 7+ years of experience in customer success and/or strategic consulting with a proven record of driving customer value and outcomes. - 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. - 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. - Strong analytical and problem-solving skills, with the ability to interpret data and develop actionable recommendations. - 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. Benefits - The starting base salary range for this role is $145,000 – $155,000 USD annually. Actual compensation may vary based on factors such as skills, experience, and location. - This role is eligible for an annual bonus and participation in Gainsight’s equity program. - 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. - Dedicated Recharge Holidays - one long weekend each quarter to relax and reset.

• Architect, orchestrate, and ensure delivery of large-scale, cross-functional initiatives that drive measurable business outcomes and maximize client success and Gainsight value. • Guide the design of scalable program governance, delivery, and measurement approaches, ensuring optimal resource deployment, margin optimization, and client satisfaction. • Execute multi-workstream software and services projects for existing customers at a program level. • Represent Gainsight as an executive sponsor in critical customer forums, executive business reviews, and SteerCo sessions, influencing decisions and building customer advocacy. • Represent Gainsight as the executive point of escalation, negotiating complex issues and ensuring client relationships remain strong and mutually beneficial. • Partner with executive sponsors (both client and Gainsight) to define both short and long-term program roadmaps and drive alignment between client business outcomes and Gainsight’s offerings. • Build and nurture trusted, executive–level relationships within client organizations, advocating for strategic partnership and executive alignment. • Support the definition of long-term account strategy by anticipating evolving client business objectives and proactively identifying opportunities for value delivery, innovation, and expansion. • Partner with internal stakeholders to identify and secure strategic cross-functional resources, influence product direction, and drive company-wide alignment for key accounts. • Serve as a visible leader and mentor within the Professional Services organization—coaching, developing, and elevating program management excellence and thought leadership. • Contribute to Professional Services practice development by creating reusable assets, methodologies, and best practices, while staying current with industry trends. • This role may require occasional travel (20%) for customer onsite meetings, team meetings, training, or company events.

• Prepare, review, and manage accurate, timely quotes within Salesforce CPQ • Partner with Sales, Finance, and Legal to ensure alignment with pricing policies, contract terms, and approval workflows • Validate deal structures, contract terms, and billing schedules for accuracy and compliance • Maintain data integrity across Salesforce CPQ and contract records throughout the quote-to-cash lifecycle • Troubleshoot and resolve quoting or contract discrepancies independently • Contribute to process improvements and documentation to enhance efficiency and scalability • Collaborate with cross-functional stakeholders to minimize errors and uphold high standards of accuracy • Support global teams by working flexible hours across US and EMEA time zones, as needed

Title: Solutions Consultant Location: USA Job Description: remote type Remote time type Full time job requisition id R-101646 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 Solutions Consultant to join our Sales team reporting to the Manager, Solutions Consultant . This role is a remote role based in the United States. In this role, you’ll play a key role in driving customer value and solution alignment by mapping business challenges to platform capabilities. This is a great opportunity for someone who thrives in a collaborative, fast-paced SaaS environment and enjoys working cross-functionally with teams like Sales, Account Management, and Customer Success. The ideal candidate brings strong skills in solution consulting, stakeholder communication, and problem-solving. What You'll Do: - Contribute to the detailed qualification of opportunities, formulation of sales strategies and technical approaches and plans. Ensure prospect/client satisfaction with all project deliverables. - Work cross-functionally with Sales, Professional Services, Marketing, and Product Management to develop relevant use cases for prospective customers. - Articulate the value of Customer Success and the Gainsight Platform to prospects and customers, either onsite or via web-conference. - Conduct business and technical discovery to uncover requirements that need to be addressed via presentations and demonstrations. - Assist in the creation of technical account configuration documentation and technical statements of work. Prepare and provide client-facing technical follow-up calls and documentation. - Participate in weekly Solution Consulting and Product Management meetings to stay up to date on current technical concepts and future product enhancements. Attend all company provided Solution Consulting enablement sessions. - Develop industry-related thought leadership while demonstrating technical expertise during the sales cycle. - Create solution presentation storyboards and configure solutions environments that tell a story and are anchored in the value-based selling approach. - Respond to technical questions received via RFP and or RFI in an accurate and timely fashion. - Meet or exceed quarterly management objectives and revenue targets. 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: - Minimum of 2 years experience in software consulting, pre-sales consulting, product management, or customer success - Experience in customer success management, account management, professional or renewal services. - Possess excellent client-facing skills and experience in dealing with client and technical teams as well as experience in presenting to C-level executives. - Ability to work autonomously while being effective within a highly driven organization. - Solid oral, written, presentation, and interpersonal communication skills. - Ability to present technical concepts to both technical and non-technical audiences. - Ability to work as part of a team to solve technical problems in varied departmental environments. - Intrinsically motivated with a strong work plan and self-development skills. Nice-to-have skills: - Knowledge of Salesforce or Gainsight architecture and data model, including integration methods such as REST APIs and ETL tools. - Knowledge of relational database concepts including specific knowledge of one of the following (MongoDB, RedShift) including expertise in SQL. - Analysis and design skills of moderate complexity - Knowledge in web application & scripting technologies, HTML, CSS, JavaScript, and SaaS applications. 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 $80,000 – $90,000 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! 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.

• Support Company-Wide Planning & Forecasting • Own revenue and cash flow forecasting end-to-end, continuously refining models to improve accuracy and timeliness • Own the 5-Year Strategic Plan • Deliver Executive & Board-Level Reporting • Support Investor Relations & M&A • Integrate AI Into the Finance Function

• Own and continuously improve the company’s core operating cadence • Drive high-priority, cross-functional strategic initiatives on behalf of the CEO • Coordinate the annual planning process end-to-end in partnership with Finance • Own the narrative and coordination for board decks, investor materials, and key executive presentations • Build and maintain the data layer that supports executive decision-making • Serve as a shared strategic resource to the Business Unit GMs and functional leaders • Provide analytical and project management support on M&A or strategic partnership evaluations as needed

Role Description We’re looking for a full-time Principal Customer Success Manager to join our CS team reporting to the VP, Customer Success. This role is a remote role based in The United States of America. In this role, you’ll play a key role in driving long-term customer growth and advocacy within Gainsight’s Strategic Accounts by: - Building trusted executive partnerships - Delivering measurable ROI - Leading outcomes that drive renewals and expansion This is a great opportunity for someone who thrives in a fast-paced, strategic, customer-facing environment and enjoys working cross-functionally with teams like Sales, Product, and Executive Leadership. The ideal candidate brings strong skills in: - Strategic account management - Executive-level communication - Customer success leadership - Data-driven value storytelling Qualifications - Over 10 years of progressive experience in Customer Success - Expert-level knowledge of Customer Success best practices - Extensive experience with highly complex, enterprise-level products - Prefers C-level engagement - Exceptional skill in navigating and leading through ambiguity - Proven leadership in cross-functional collaboration - Demonstrated thought leadership in the Customer Success industry - Experienced in developing and delivering executive-level presentations Requirements - Manage approximately five clients in Gainsight's Strategic Accounts segment - Proactively manage risks and foster adoption and outcomes - Provide mentorship and leadership to team members - Develop and lead strategic client partnerships - Quantify, deliver, and strategically communicate ROI for clients - Act as a trusted advisor and thought leader - Cultivate deep executive-level relationships within client organizations - Architect and deliver high-impact customer deliverables - Leverage Gainsight technology to track client goals and success metrics - Drive cross-functional initiatives within Gainsight - Collaborate strategically with Account Executives - Represent Gainsight as a recognized industry expert Benefits - Starting base salary range: $155,000 - $165,000 USD annually - Eligible for an annual bonus and participation in Gainsight’s equity program - Comprehensive benefits package including fully covered medical premiums (employee-only) - Flexible PTO - 401(k) plan - Dental and vision coverage - Remote work options - $10,000 lifetime fertility stipend - Access to coworking spaces around the globe - Dedicated Recharge Holidays - one long weekend each quarter

Role Description We’re looking for a full-time Xactly Technical Admin to join our Sales team reporting to the Revenue Compensation Manager. This role is a remote role based in the United States. In this role, you’ll play a key role in enabling accurate, scalable, and efficient sales compensation operations by managing and optimizing the Xactly Incent platform and translating complex compensation plans into reliable system logic. This is a great opportunity for someone who thrives in a fast-paced, highly collaborative environment and enjoys working cross-functionally with teams like Sales, Customer Success, Finance, RevOps, and GTM Operations. The ideal candidate brings strong skills in Xactly system administration, data analysis and reporting, and stakeholder collaboration. What You'll Do: - Manages and administers the Xactly Incent platform, including configuration, maintenance, and troubleshooting to ensure optimal performance. - Manages permissions, access, personalization, new user set up, and similar system operations and settings for Xactly users. - Translates compensation plan documents into system logic, ensuring accurate and auditable calculation outputs. - Designs and maintains system workflows for plan changes, exceptions, and adjustments. - Performs monthly, quarterly, and annual system setup, including User/Position management and hierarchy updates. - Conducts UAT Testing to ensure system accuracy. - Provides technical guidance during plan design discussions, advising on system capabilities and constraints. - Troubleshoots and resolves Xactly configuration issues as they arise. - Collaborates with RevOps and GTM team to implement commission and bonus plans, ensuring seamless data integration and process efficiency. - Develops and maintains detailed documentation for Xactly processes, configurations, and procedures to ensure transparency and knowledge sharing. - Identifies opportunities to streamline and automate compensation processes, reducing manual intervention and cycle time. - Creates and monitors reporting for end users, creating transparency through easily understandable reports and dashboards that provide clear insights into commission and/or bonus structures and performance metrics. - Provides technical support, troubleshooting, and training to the commission team, equipping them with the knowledge to train end users effectively. - Develops and maintains the comprehensive Functional Requirement Documentation (FRD) for the current plan year, detailing all functional components, business rules, and data mapping requirements. - Continuously assesses and enhances system functionality by staying informed of product updates and new features and implements relevant improvements. - Ensures data security and integrity within the Xactly system, adhering to company policies and regulatory requirements. 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. Qualifications - 3-5 years of experience with the Xactly platform, focusing on system configuration. - Bachelor’s degree in Computer Science, Information Systems, or Business Administration (or equivalent combination of education and experience). - Capable of managing multiple priorities and delivering high-quality results within deadlines. - Proficiency in data analysis and reporting, with the ability to manage complex datasets and reporting solutions. - Proven ability to translate business requirements into system logic and maintain accurate, auditable calculations. - Excellent problem-solving skills, showcasing attention to detail and precision. - Strong collaboration skills, with the ability to communicate effectively with internal stakeholders. Requirements - Experience with Xactly CEA or Xactly Connect (nice-to-have). - Experience with Salesforce or other CRM systems (preferred). - Xactly Certified Administrator or equivalent certification (highly preferred). - Familiarity with data visualization tools (e.g., Sigma, Tableau, Power BI) for enhanced reporting capabilities. Benefits - The starting base salary range for this role is $80,000 to $90,000 USD annually. - Actual compensation may vary based on factors such as skills, experience, and location. - This role is eligible for an annual bonus and participation in Gainsight’s equity program. - 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. - Dedicated Recharge Holidays - one long weekend each quarter to relax and reset.

• Own the end-to-end pricing and packaging strategy across Gainsight’s product suite by conducting analysis, modeling options, and making recommendations that align customer value, product adoption and market dynamics • Lead the transition from seat-based pricing toward usage-based or hybrid monetization models where appropriate • Develop long-term monetization strategies that support Gainsight’s product roadmap and AI-driven platform evolution • Present monetization performance and key pricing decisions to the board and Executive Leadership Team as needed • Partner cross-functionally with Product, Sales, RevOps and Finance to ensure monetization strategies are aligned with customer needs and company goals • Partner with and oversee deliverables from external pricing consultancies as needed • Lead pricing and packaging design for new products and launches in partnership with the product GMs • Design and evolve value metrics, tiering and packaging strategy, bundling, cross-sell and upsell motions and a cross-functional governance process • Conduct competitive research and market analysis to inform pricing strategy and GTM decisions, adapt pricing strategy to new agentic and usage-based models • Build and maintain financial models to forecast the impact of pricing and packaging changes, partnering with Finance to support business case development • Track and report on monetization KPIs, identifying areas of friction, opportunity, or optimization across pricing, adoption, and retention • Partner with RevOps on our CPQ transformation • Support acquisition integration from a pricing/packaging perspective by assessing commercial models and contributing to launch plans

• Own end-to-end contract lifecycle management for a broad portfolio of commercial agreements, including SaaS subscription agreements, NDAs, vendor agreements, and amendments • Draft, review, redline, and negotiate contract terms directly with customers and vendors, including real-time discussion and problem solving, escalating to legal counsel as needed • Serve as the primary point of contact and subject matter expert for contract-related inquiries from Sales, Finance, and Customer Success teams, providing timely guidance and enabling deal velocity • Develop, maintain, and continuously improve contract templates, clause libraries, fallback positions, and contracting playbooks to standardize and streamline the contracting process • Identify process gaps and lead initiatives to improve contracting workflows, reduce cycle times, and scale the contracts function in support of business growth • This role may require occasional travel (up to 5%) for team meetings, training, or company events