Senior Director, Pricing & Packaging

About the 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.

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

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

Qualifications

• 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

  • Experience with Salesforce CPQ

Benefits

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.