Gainsight

Manage and optimize PS operations, implement AI initiatives, and lead distributed teams to support multi-product services. | 7+ years in PS Operations or RevOps, experience with PSA platforms, AI/automation in workflows, and managing distributed teams. | 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 Senior Manager to join our Services team reporting to the Senior Director, Services Products. This role is a remote role based in the United States. In this role, you’ll play a key role in scaling and optimizing Gainsight’s Professional Services operations by driving operational excellence across PS Operations and Deal Desk for a multi-product services business. This is a great opportunity for someone who thrives in a fast-paced, execution-focused environment and enjoys working cross-functionally with Sales, Professional Services, Finance, Partner, and Product teams. The ideal candidate brings strong skills in operational leadership, process optimization, and managing global teams. What You'll Do: Manage the repository of PS operational content, including offering calculators, SOW templates, SKUs, and packaging. Execute the PS offer release process, ensuring coordination across Sales, Finance, Legal, and Delivery. Enforce opportunity data standards and manage approval workflows to ensure efficient SOW redlines and deal triage. Maintain naming, SKU, and pricing consistency to support repeatability and partner scale. Administer the internal PS tech stack and ensure governance and output standards are met. Implement prioritized AI and automation initiatives to increase accuracy and reduce manual effort. Collaborate with Product and internal tooling teams to operationalize AI use cases within PS workflows. Maintain the PSA platform, ensuring data accuracy, reporting reliability, and system stability. Support operations for SFDC, Services CPQ, Trello scoping workflows, and Workrails contract automation. Monitor data quality, forecasting, utilization, and delivery insights to drive continuous improvement. Ensure systems consistently support the operational needs of ARR services and partner delivery. Manage PS Sales Operations processes, including pricing governance, quoting workflows, and partner services coordination. Update and distribute enablement materials such as offer guides, battle cards, and objection handling frameworks for sellers and partners. Oversee automated partner workflows to ensure partner-delivered engagements adhere to standardized processes. Partner with Sales leadership to resolve operational friction and improve the seller experiences Manage and mentor a team of four analysts across the US and India. Guide the Deal Desk team to focus on strategic operational impact and efficient sales support. Foster analyst autonomy in reporting, data management, and daily problem-solving. Uphold clear standards, operating rhythms, and documentation to ensure team consistency. 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: 7+ years in PS Operations, Deal Desk, or RevOps with experience managing operational workflows in a PS business. Experience with PSA platforms. Experience executing AI and automation initiatives in operational workflows. Proven ability to lead distributed teams and collaborate effectively with cross-functional partners. Strong operational discipline and comfort working in a multi-product environment. Experience maintaining enablement materials such as offer guides, playbooks, and positioning briefs for Sales and partners. 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 – $150,000 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. Gainsight helps you grow your business faster and more efficiently with a single product suite that enables you to deliver value to today’s always-on customer at every moment of their journey. With Gainsight’s Customer Communities, Product Experience, Customer Success, and Customer Education products, it’s never been easier to scale your business, grow your revenue, and retain your customers. Winning The Human Way Leading the industry with award-winning software is rewarding. But the best moments—the ones we tell our moms about—happen when we’re together with our customers, colleagues, and partners. Our mission is to prove that you can win in business by being Human-First. For us, that means cultivating innovative ideas, nourishing a deep connection to our communities, introducing industry-defining products, and never saying no to a moment of childlike joy.

Developing full-stack applications and APIs, leading technical projects, and integrating cloud services. | Experience with TypeScript, React, Node.js, API development, and cloud platforms; senior-level experience. | TBD Gainsight helps you grow your business faster and more efficiently with a single product suite that enables you to deliver value to today’s always-on customer at every moment of their journey. With Gainsight’s Customer Communities, Product Experience, Customer Success, and Customer Education products, it’s never been easier to scale your business, grow your revenue, and retain your customers. Winning The Human Way Leading the industry with award-winning software is rewarding. But the best moments—the ones we tell our moms about—happen when we’re together with our customers, colleagues, and partners. Our mission is to prove that you can win in business by being Human-First. For us, that means cultivating innovative ideas, nourishing a deep connection to our communities, introducing industry-defining products, and never saying no to a moment of childlike joy.

Lead and scale a customer success team, develop strategies for customer retention and growth, and collaborate across teams to ensure customer success. | Over 8 years in customer success or related fields, with at least 5 years in leadership, experience with global enterprise customers, and strong analytical skills. | 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. Gainsight helps you grow your business faster and more efficiently with a single product suite that enables you to deliver value to today’s always-on customer at every moment of their journey. With Gainsight’s Customer Communities, Product Experience, Customer Success, and Customer Education products, it’s never been easier to scale your business, grow your revenue, and retain your customers. Winning The Human Way Leading the industry with award-winning software is rewarding. But the best moments—the ones we tell our moms about—happen when we’re together with our customers, colleagues, and partners. Our mission is to prove that you can win in business by being Human-First. For us, that means cultivating innovative ideas, nourishing a deep connection to our communities, introducing industry-defining products, and never saying no to a moment of childlike joy.

Designing and configuring SaaS solutions for clients, serving as a technical advisor, and managing multiple customer projects. | 3-6 years in SaaS or technical consulting, experience with CRM and data tools, strong communication skills, and familiarity with customer success principles. | 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 Architect to join our professional services team reporting to the Senior Manager, Technical Delivery. This role is a remote role based in the United States. In this role, you’ll play a key role in driving long-term customer success by ensuring Gainsight environments are optimized for adoption, scalability, and ongoing value. You’ll deliver this impact by serving as a trusted technical advisor post-onboarding—partnering with customers to design tailored solutions, lead configuration and optimization efforts, and align technical capabilities with evolving business goals. This is a great opportunity for someone who thrives in a consultative, customer-facing environment and enjoys working cross-functionally with Customer Success, Product, and Engineering teams. The ideal candidate brings strong skills in solutions architecture, technical configuration and optimization, and translating business requirements into scalable technical solutions. What You'll Do: Understand Gainsight products, their features, functions and recognize how they can be used to solve problems and create solutions for your customers. Serve as a technical strategist to drive adoption and expansion for existing Gainsight clients. Partner with Customer Success Managers to align technical initiatives with client outcomes. Lead discovery and requirement-gathering sessions to understand and document business needs. Design and configure Gainsight solutions based on best practices and client-specific goals. Act as a seamless extension of your customers’ operations team. Deliver enablement sessions to empower Gainsight Admins and key stakeholders. Build strong, trust-based relationships with clients, including technical and executive stakeholders. Proactively identify risks or blockers and collaborate cross-functionally to resolve them. Contribute to internal best practices, templates, and delivery frameworks. Track project hours and maintain target utilization. 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: Must-have skills or experience: 3 to 6 years of experience in Professional Services, Technical Consulting, or Enterprise SaaS implementation. and a BA/BS degree (or equivalent combination of education and experience), required. Hands-on experience with CRM platforms (Salesforce or Dynamics preferred), databases, and data integration tools. Strong understanding of Customer Success principles and ability to translate business needs into scalable technical solutions. Experience managing multiple customer projects simultaneously (5–10 engagements). Familiarity with agile and waterfall delivery methodologies. Executive presence and confidence in communicating with both technical and business leaders. Excellent communication, facilitation, and presentation skills. Ability to thrive in a fast-paced, dynamic environment. Prior experience with Gainsight CS and/or Customer Success Operations (CS Ops) is highly preferred. Experience in a post-onboarding or ongoing account management role is strongly preferred. Nice-to-have skills or experience: Scripting experience in Python or Node.js to support custom solutions and automation is a plus. Salesforce certification or experience is a plus. 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 – $105,000 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. Gainsight helps you grow your business faster and more efficiently with a single product suite that enables you to deliver value to today’s always-on customer at every moment of their journey. With Gainsight’s Customer Communities, Product Experience, Customer Success, and Customer Education products, it’s never been easier to scale your business, grow your revenue, and retain your customers. Winning The Human Way Leading the industry with award-winning software is rewarding. But the best moments—the ones we tell our moms about—happen when we’re together with our customers, colleagues, and partners. Our mission is to prove that you can win in business by being Human-First. For us, that means cultivating innovative ideas, nourishing a deep connection to our communities, introducing industry-defining products, and never saying no to a moment of childlike joy.

Manage end-to-end enterprise software implementation projects, coordinate with executive sponsors, develop project plans, track scope and risks, and mentor team members. | Bachelor's degree or equivalent, 5+ years managing enterprise software or professional services projects, strong communication and stakeholder management skills, knowledge of waterfall and agile methodologies, and experience with SaaS platforms preferred. | About Gainsight: Gainsight is the 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 Strategic Engagement Manager (SEM) to join our Professional Services team, reporting to the SEM Manager. This role is a remote role based in the United States. In this role, you’ll play a key role in driving successful enterprise-level implementations of the Gainsight platform for our customers by owning the end-to-end onboarding and delivery lifecycle. This is a great opportunity for someone who thrives in a fast-paced, client-facing environment and enjoys working cross-functionally with teams like Sales, Customer Success, Product, and Engineering. The ideal candidate brings strong skills in enterprise project management, stakeholder communication, and enterprise software implementation. What You'll Do: Execute complex software implementation projects while partnering closely with executive-level client sponsors to ensure alignment on scope, timeline, and desired business outcomes. Drive onboarding efforts for new and existing customers, prescribing best-practice recommendations that tie directly to their objectives. Develop and maintain detailed project plans, work breakdown structures, and communication cadences to ensure on-time, on-budget delivery. Track project scope and, when necessary, estimate and execute change orders in partnership with the customer. Produce comprehensive weekly status reports and executive communications to keep internal and external stakeholders informed. Proactively identify project risks and issues, developing and executing mitigation plans to maintain project health. Coach and mentor project team members (often across multiple time zones) to facilitate effective teamwork and knowledge transfer. Contribute to the continuous improvement of Professional Services by creating templates, policies, and tools that scale our delivery capabilities. This is not a complete list of responsibilities, and the scope of the role may evolve with the needs of the team and business. What We're Looking For: Bachelors Degree (or equivalent experience, preferably with Project Management certification (e.g., PMP, PRINCE2) and/or 5 years of related experience 5+ years of experience managing enterprise-grade software implementation or professional services projects, or in a related customer-facing consulting role. Demonstrated success leading cross-functional, geographically dispersed project teams of up to 5 members on engagements valued at $0.5M+. In-depth knowledge of both waterfall and agile project management methodologies and tools. Executive presence with highly developed communication, presentation, and stakeholder-management skills. Proven ability to create structure in ambiguous situations and design effective delivery processes. Experience working with complex, multi-divisional, multi-geographical customers. Up to 10-15% travel for customer onsite meetings. Prior experience implementing Customer Success or CRM platforms (e.g., Gainsight, Salesforce) preferred. Exposure to SaaS business models and metrics preferred 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 $71,000 – $91,200 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! 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 recruiting@gainsight.com. 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. Gainsight helps you grow your business faster and more efficiently with a single product suite that enables you to deliver value to today’s always-on customer at every moment of their journey. With Gainsight’s Customer Communities, Product Experience, Customer Success, and Customer Education products, it’s never been easier to scale your business, grow your revenue, and retain your customers. Winning The Human Way Leading the industry with award-winning software is rewarding. But the best moments—the ones we tell our moms about—happen when we’re together with our customers, colleagues, and partners. Our mission is to prove that you can win in business by being Human-First. For us, that means cultivating innovative ideas, nourishing a deep connection to our communities, introducing industry-defining products, and never saying no to a moment of childlike joy.

The Senior Director, Digital Customer Success will build and lead a digital-first engagement model to enhance customer experiences across the entire lifecycle. This role involves overseeing strategy and execution in areas such as digital customer success, community engagement, and AI integration. | Candidates should have over 10 years of experience in customer success or digital programs, with a proven track record in leading large-scale digital transformations. Familiarity with AI tools, community-led growth, and metrics-based reporting is essential. | About Gainsight: Gainsight is the 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 Senior Director, Digital CS to join our Customer Success team reporting to the Chief Customer Officer. This role is a remote role based in the United States. In this role, you’ll play a key role in building and leading our digital-first engagement model, enabling scalable, tech-powered customer experiences across the full lifecycle and across our entire customer operating system. This role spans the entire post-sale customer journey, overseeing both strategy and execution across five major domains: Digital Customer Success and Tech-Touch Programs, Community and Education Strategy, Product Experience, AI and Agentic Customer Engagement, and Support Collaboration and Deflection Efficiency. This is a rare opportunity for a senior operator and strategist to lead a modern, data-driven, and AI-augmented approach to Customer Success. You’ll partner deeply with Product, Support, Education, RevOps, and Marketing to execute a unified digital motion. What You'll Do: Build a unified digital CS strategy that scales across all segments and products driving efficiency, retention, and product adoption through digital channels. Design and operationalize tech-touch and hybrid engagement models including digital success planning and lifecycle-based journey orchestration. Embed automation and AI into the customer journey from onboarding flows and stakeholder alerts to in-app engagement and intelligent nudges. Own the digital engagement tech stack, including Gainsight, PX, AI copilots/agents, knowledge systems, community platforms, and LMS tools. Drive community-led success by integrating digital CS with our customer community and education functions supporting peer learning, events, and enablement at scale. Collaborate with Support on agentic strategies, chatbot design, and proactive deflection methods to reduce case volume and improve self-service rates. Define and manage a KPI framework that demonstrates the impact of digital success programs on retention, NRR, product usage, and cost-to-serve. Lead a high-performing team of digital CS managers, program owners, and cross-functional partners to deliver outcomes at scale. Drive change management efforts by navigating organizational shifts and executing strategic transformation initiatives across entire Customer Success organization, not limited to digital strategies Develop and mentor leadership talent within the GTM team, with a focus on growing future managers and strengthening organizational depth. Actively engage with Executive Leadership team to align and advance company-wide Digital Customer Success priorities, including product innovation and prioritization. This is not a complete list of responsibilities, and the scope of the role may evolve with the needs of the team and business. What We're Looking For: 10+ years of experience in CS, digital programs, or scaled operations roles in B2B SaaS Proven track record leading large-scale digital CS transformations (ideally across multiple segments) Familiarity with AI tooling, journey orchestration, and agentic models in CS Strong understanding of community-led growth, customer education, and LMS strategies Experience with metrics-based storytelling and reporting to senior leadership A builder mindset where you bring structure, speed, and clarity to ambiguous problems A strong sense of ownership and urgency; you’re outcome-oriented and scrappy 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 $154,000-$200,200 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! 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 recruiting@gainsight.com. 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. Gainsight helps you grow your business faster and more efficiently with a single product suite that enables you to deliver value to today’s always-on customer at every moment of their journey. With Gainsight’s Customer Communities, Product Experience, Customer Success, and Customer Education products, it’s never been easier to scale your business, grow your revenue, and retain your customers. Winning The Human Way Leading the industry with award-winning software is rewarding. But the best moments—the ones we tell our moms about—happen when we’re together with our customers, colleagues, and partners. Our mission is to prove that you can win in business by being Human-First. For us, that means cultivating innovative ideas, nourishing a deep connection to our communities, introducing industry-defining products, and never saying no to a moment of childlike joy.