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 storytelling

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
Salesforce CPQ experience

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 evolve with the needs of our customers. When people with diverse strengths, a strong sense of community, and true passion for our mission come together, they drive greater impact and create lasting value. What underpins it all is a culture that offers the stability, trust, and support that people need - not just to do the job, but to show up as themselves and feel connected to the work they do. Gainsters love working here for several reasons. Here are a few:

Our Compensation and Benefits: At Gainsight, we believe great work happens when teammates feel fully supported.

The starting base salary range for this role is $215,000 – $230,000 USD annually. This role is also eligible for commission based on performance and participation in Gainsight’s equity program. 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.

Our Core Values: We are guided by our values and our mission to be living proof you can win in business while being Human-First. Learn more here.

Our Growth Opportunities: From mentoring to career development opportunities, we’re passionate about helping our teammates learn, grow, and thrive.

Our Parody Videos: No explanation needed. Just watch them here!

If this sounds like the right role for you, we’d love to hear from you.

Additional Information:

We’re committed to creating an inclusive, fair, and transparent hiring process. As an equal opportunity employer, we celebrate diversity and are committed to creating a welcoming experience for all candidates.

If you require accommodations or have questions about how your personal data will be used during the hiring process, please let the recruiting team know.

If you are based in San Francisco, we will consider qualified applicants with arrest and conviction records, in accordance with the San Francisco Fair Chance Ordinance.

Senior Director, Pricing & Packaging