Senior Director, Pricing & Packaging

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