Pricing & Packaging Specialist

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 Pricing and Packaging Strategist 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 shaping and scaling Gainsight’s monetization strategy by defining pricing and packaging frameworks that drive growth across a multi-product SaaS portfolio. This is a great opportunity for someone who thrives in a highly analytical, fast-growing SaaS environment and enjoys working cross-functionally with teams like Product, Sales, Marketing, Customer Success, Finance, and GTM Operations. The ideal candidate brings strong skills in pricing and packaging strategy, financial modeling and analysis, and translating market and customer insights into clear, actionable recommendations. 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 based on customer value and market dynamics. Partner cross-functionally with Product, Sales, RevOps and Finance to ensure monetization strategies are aligned with customer needs and company goals. 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 Customer Success and usage-based models. Contribute to GTM planning for new products and launches, including positioning, packaging, segmentation, and initial pricing hypotheses. 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. 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: 8+ years of experience in pricing strategy, business operations, or GTM strategy, ideally in B2B SaaS or tech Strong analytical and financial modeling skills, comfortable in Excel/Sheets, and with BI tools (e.g., Looker, 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, value-based pricing, and product-led or AI-driven GTM strategies Nice-to-have skills: Experience working in a PE-backed company or high-growth SaaS environment Exposure to product launches, packaging changes, or monetization experimentation Salesforce CPQ experience Consulting or MBA background is a plus, but not required 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 evol ... (truncated, view full listing at source)