Senior Director, Pricing & Packaging

Gainsight

. 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 .

Posted 4/22/2026full-timeRemote • California, Rhode Island, South Carolina, Tennessee, Texas • 🇺🇸 United StatesSenior💰 $215,000 - $230,000 per yearWebsite

About the role

Key responsibilities & impact

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

What you’ll need

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

Benefits

Comp & perks

fully covered medical premiums (employee-only)
flexible PTO
401(k) plan
dental and vision coverage
remote work options
$10,000 lifetime fertility stipend
access to coworking spaces around the globe
dedicated Recharge Holidays - one long weekend each quarter to relax and reset

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

pricing strategyfinancial modelingcompetitive researchmarket analysisdata insightsExcelBI toolsmonetization strategiespackaging designGTM strategy

Soft Skills

analytical skillsproblem-solvingcommunicationinfluence stakeholdersstorytellingcross-functional collaborationcustomer needs alignmentpresentation skillsleadershipstrategic thinking