Gainsight, Inc

Drive North America sales growth by delivering data insights, aligning cross-functional teams, and managing sales operations. | Requires 4+ years relevant experience, MBA or equivalent, strong analytical and communication skills, and ability to manage multiple priorities in a fast-paced SaaS environment. | 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 Sales Operations Manager to join our Sales team reporting to the SVP, Revenue Operations. This role is a remote role based in the USA. In this role, you'll play a key role in accelerating North America sales growth and performance by partnering closely with the NA SVP of Sales to drive business rhythm, deliver data-informed insights, and align cross-functional execution. This is a great opportunity for someone who thrives in a fast-paced, high-growth SaaS environment and enjoys working cross-functionally with teams like Finance, Demand Gen, and Customer Success. The ideal candidate brings strong skills in sales analytics, strategic communication, and operational execution. What You'll Do: Insights, Analytics & AI Use dashboards and reports (Salesforce, Sigma, Gainsight) to pull together a regular view of pipeline health, rep performance, and forecast accuracy for the NA Sales leader. Spot patterns and anomalies in the data and flag them to the team with a clear summary of what you’re seeing. Work with the Revenue Operations tech team to flag data quality issues and support improvements to our core sales tools (Salesforce, Gainsight, Gong.io). Run ad hoc analyses to support annual planning inputs such as territory design and quota distribution. Identify, evaluate, and implement new AI technologies that improve seller productivity and pipeline visibility (Notion, Claude, Gong.io, Gainsight). Cross-Functional Collaboration Build working relationships with teams like Demand Gen, Customer Success, and Product by sharing pipeline updates and helping coordinate on shared go-to-market initiatives. Communicate cross-functional requests clearly and follow up to keep shared work on track. Identify process gaps that slow down sellers or create unnecessary friction, and raise them with the right teams. Proactively identify ways to make day-to-day work easier for frontline sellers and sales managers, using provided tech stack and AI. Sales Planning & Execution Assist with annual planning activities such as pulling territory data, organizing quota inputs, and maintaining headcount tracking lists. Track sales incentive plan performance and flag discrepancies or anomalies to Sales Comp, Finance, and leadership for follow-up. Help maintain the NA Sales team’s process documentation and operating playbook, keeping it current and easy to use. Strategic Partnership Support the North America Sales leader with day-to-day operational needs, helping turn priorities into action. Help coordinate recurring sales meetings and reviews by preparing agendas, taking notes, and following up on action items for QBRs, pipeline reviews, and weekly forecast calls. Draft internal communications and meeting materials (e.g. summaries, recaps, follow-up notes) on behalf of the NA Sales leader. Track open action items and key initiatives, helping keep the sales leadership team on schedule and accountable. This role may require occasional travel up to 15% for team meetings, training, or company events. 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: Must-have skills or experience: 4+ years of relevant experience and MBA or equivalent combination of education and experience), required. Synthesize complex information into clear, concise narratives for senior audiences. Juggle multiple priorities, manage stakeholders, and drive to closure without being asked twice. Intellectual curiosity and a bias toward data; you ask 'why' before drawing conclusions. Comfortable with a fast-paced, high-growth SaaS environment where priorities shift Nice-to-have skills or experience: High executive presence and comfort operating in ambiguity with autonomy. Low ego, high collaboration: you elevate others and get things done behind the scenes. What Success Looks Like: Success in this role will be measured by outcomes such as Meeting & Cadence Execution of recurring meetings (QBRs, forecast calls, pipeline reviews) delivered on time with agenda and pre-read distributed in advance. Reporting Timeliness & Accuracy On-time delivery rate of weekly/monthly dashboards and reports Impact positively the NA GTM execution, Pipeline growth and health, deal review, forecasting accuracy, performance management, and GRR. 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 $110,000 - $120,000 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 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.

Lead pricing and packaging strategy to drive monetization and revenue growth across product portfolio. | 10+ years in pricing strategy or GTM strategy in B2B SaaS, strong financial modeling, executive communication, and cross-functional leadership. | 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 Director, Pricing and Packaging to join our Sales team reporting to the EVP, GTM Strategy & Operations. This role is a remote role based in The United States. In this role, you’ll play a key role in driving Gainsight’s monetization strategy and long-term revenue growth by leading the evolution of pricing and packaging across its product portfolio, including the transition to usage- and value-based models. This is a great opportunity for someone who thrives in a highly strategic, data-driven SaaS environment and enjoys working cross-functionally with teams like Product, Sales, Finance, Marketing, and Customer Success. The ideal candidate brings strong skills in pricing strategy, financial modeling, and executive stakeholder communication. What You'll Do: 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 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: 10+ years of experience in pricing strategy, business operations, or GTM strategy, ideally in B2B SaaS or technology Strong analytical and financial modeling skills, comfortable in Excel/Sheets, and with BI tools (e.g., Sigma) Experience conducting competitive and market research with the ability to turn insights into clear recommendations Ability to communicate clearly and influence stakeholders across teams, from Product to Sales to Finance Familiarity with SaaS business models, usage and outcome based pricing and product-led or AI-driven GTM strategies Exceptional analytical and problem-solving skills Ability to translate data insights into actionable pricing strategies Strong executive communication and storytelling Nice-to-have skills or experience: Experience working in a PE-backed company or high-growth SaaS environment Prior experience in pricing consulting or strategic pricing advisory strongly preferred (e.g., Simon-Kucher, Teneo, BCG, etc.) Experience leading pricing transformations at growth-stage or enterprise SaaS companies Pricing experience with leading product launches, packaging changes, or monetization experimentation Salesforce CPQ experience 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 $215,000 – $230,000 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. 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 complex sales cycles and pipelines, engage C-suite stakeholders, conduct product demos, respond to RFPs, collaborate with Customer Success, and achieve sales quotas. | Minimum 5 years enterprise SaaS sales experience, BA/BS degree or equivalent, proven quota achievement, ability to manage multi-stakeholder sales cycles, and strong communication skills. | 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. What You'll Do: Follow and manage the Gainsight Sales Process Achieve sales quota for assigned territory and/or accounts Maintain appropriate proactive sales development activity to ensure healthy pipeline management Execute a thorough discovery process understanding customer requirements Articulate value messaging related to driving customer outcomes Manage complex, multithreaded sales cycles across all stakeholders Overcome technical and business objections of prospective customers as necessary Conduct online or onsite product demonstrations to qualified prospects as necessary Collaborate with Gainsights Customer Success department to drive renewals Respond to RFPs for qualified business opportunities where Gainsight is a fit Work with Gainsight’s Professional Services organization to evaluate training and consulting needs to support implementations Develop and maintain industry and competitive product and market knowledge Maintain a thorough understanding of the Gainsight product and services offered Gain an understanding of Gainsight’s use in the industry, as well as best practices Be a subject matter expert for your designated industries and territory Sales Administration Work with Customer Success to define and support prospecting efforts within assigned territory Enter new leads, contact data, log calls and other sales information into SFDC for prospects, partners and customers Prepare formal proposals, produce price quotes, work with management on contract negotiations, and coordinate the gathering of all necessary paperwork to process orders Investigate and resolve customer problems with releases, payments, product use or implementation (as required) Provide feedback (customer/prospect needs, industry trends, market perceptions, competitive intelligence, etc.) to company management, Marketing and Product Management teams Conduct online webinars as a means of generating qualified leads Plan, promote and conduct round table events in key locations within your territory Travel to and attend customer and prospect meetings, trade shows, conferences and round tables; 25-30% travel per year What We're Looking For: Bachelor's degree or equivalent experience Minimum of five years experience selling Enterprise Solutions (SaaS and services) into Fortune 1000 companies Comfort and expertise calling on and presenting to C-Suite level contacts, six figure deal sizes and 6-12 month sales cycles Proven track record of identifying business issues and creating value while managing multiple stakeholders and decision makers in a complex sales cycle Demonstrated history of quota achievement/overachievement Someone who is highly competitive, entrepreneurial and self-driven Experience in the Customer Success and Product Experience fields working with key decision makers such as Chief Revenue Officers, Chief Customer Officers, leaders in Customer Success and Product Management and Marketing strategizing to drive for mutual success. Job Benefits At Gainsight, we don't believe in doing things as a "means to an end." Life is too short to have anything short of a joyful work environment that we passionately believe in. We think that "work vs. life" is a false choice created by pundits, cynics and consultants. We also believe that any community (like a company) needs a ton of diversity and a very small number of things that bring us together. Here are Our 5 Values Golden Rule: We try to practice the Golden Rule ("Do unto others..." and that sort of thing) by exercising reliability, trust and giving back to each other and our community. Success for All: We believe that success for our stakeholders—whether our teammates, clients or shareholders—comes with a sincere focus on continuous learning, selfless teaching and making a difference in each other’s lives. Child-like Joy: We aspire to experience child-like joy in our work and lives, injecting a spirit of passion, optimism and laughter into everything that we do. Shoshin: We believe in a beginner’s mind. Don’t surround yourself with people like you--diversity breeds creativity. Stay Thirsty, My Friends: We believe in a totally internally-driven strive for greatness. The solution is think more, not doing more. Why You’ll Love It Here Our Attitude: We’ve created a new industry from scratch, and we’re on the fast track! Our Leadership: We offer the leading tech solution for driving Customer Success. Our ROI: Reduce customer churn, increase up-sell, and improve customer satisfaction. Our Technology: Best in class software, Deep Salesforce.com hook, predictive analytics, and a beautiful user interface. Our Impact: We help our customers make millions of dollars more per year. Our Clients: Big companies like Linkedin, Tableau, Box, Adobe, Marketo, and many others. Our Team: Tech all-stars from Facebook, SFDC, and others (and top consulting firms like BCG and McKinsey!). Our Values: They are unique - Golden Rule, Success for All, Child-like Joy, Shoshin, and Stay Thirsty, My Friends. 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.