Senior Director, Pricing & Packaging

Gainsight

1d•Remote

About The Position

Gainsight is building the AI-driven future of customer success, from retention to growth, with its AI-powered retention engine and CustomerOS platform. The platform orchestrates the customer journey and is trusted by over 2,000 companies. This full-time Senior Director, Pricing and Packaging role joins the Sales team, reporting to the EVP, GTM Strategy & Operations. It is a remote role based in The United States. The position is crucial for 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. It's an opportunity for someone who thrives in a strategic, data-driven SaaS environment and enjoys cross-functional collaboration with teams like Product, Sales, Finance, Marketing, and Customer Success. The ideal candidate should possess strong skills in pricing strategy, financial modeling, and executive stakeholder communication.

Requirements

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 Haves

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

Responsibilities

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
Occasional travel for team meetings, training, or company events