VP, Sales

Job Description:

Job Description:

Why Gainsight?

At Gainsight, our mission is to be living proof you can win in business while being human first.

Our industry-leading platform helps companies of all sizes and industries achieve durable growth through customer-led growth strategies (Gainsight CS), product-led growth strategies (Gainsight PX), and community-led growth strategies (inSided). With Gainsight, it’s never been easier for customer success, product, and community engagement teams to scale efficiently, create alignment, and have a holistic view of their customers—all of which help increase product adoption, prevent churn, and grow customer communities. Our software is used by hundreds of companies, including nearly 200 publicly traded organizations and industry leaders such as GE Digital, SAP Concur, and Box.

Gainsight joined the Vista Equity Partners portfolio in 2020. In 2021, we won their Excellence in Engineering award in recognition for our product and engineering advancements.

A remote-friendly company, we have offices in the US, UK, Netherlands, Israel, and India. Gainsight was certified as a Great Place to Work in 2021. It has also been named as one of the top 100 private cloud companies in the world by Forbes, one of the fastest-growing private companies in America by Inc. Magazine, and one of 20 Great Workplaces in Tech by Fortune Magazine.

With diversity and inclusion at the forefront of our core values, we promote a culture that celebrates diversity and inclusiveness regardless of, but not limited to, race, gender, sexual orientation, family status, religion, ethnicity, national origin, physical disability, veteran status, or age.

Vice President of Sales

Location: [Remote]

About the Role

Gainsight is seeking a dynamic Vice President of Sales to lead our high-performing sales team and drive strategic revenue growth. In this critical role, you will define and execute the sales strategy for our customer success solutions, ensuring alignment with our mission to help businesses retain customers and grow revenue through exceptional customer success practices. You will lead a talented team of sales professionals, foster cross-functional collaboration, and engage directly with C-level executives to close complex deals and build lasting partnerships.

What You’ll Do

Sales Strategy and Leadership

• Develop and implement a scalable sales strategy to drive new customer acquisition and expand existing accounts.

• Define and execute on a go-to-market plan that aligns Gainsight’s solutions with market opportunities and customer needs.

• Lead and inspire a team of sales professionals across key segments, including Commercial, Enterprise, and Strategic

• Establish clear goals, metrics, and KPIs to monitor team performance and ensure consistent revenue growth.

Team Development and Coaching

• Recruit, train, and mentor a high-performing sales team, fostering a culture of collaboration, accountability, and innovation.

• Implement best practices for sales process management, pipeline development, and forecasting.

• Provide regular coaching and professional development to drive individual and team success.

Customer and Market Engagement

• Personally engage in high-value sales opportunities, leveraging your expertise to close six- and seven-figure SaaS deals.

• Build relationships with C-suite executives, establishing Gainsight as a trusted partner in customer success.

• Analyze market trends, competitive landscape, and customer feedback to inform product positioning and strategic planning.

Collaboration and Cross-Functional Alignment

• Partner with Marketing, Product, Customer Success, and other internal teams to ensure seamless customer experiences.

• Align sales efforts with company goals, driving innovation and operational excellence across the organization.

• Serve as a key member of Gainsight’s executive team, contributing to overall company strategy and growth initiatives.

What We’re Looking For

Experience and Expertise

• 10+ years of proven success in sales leadership roles within the SaaS or technology sector, with a strong emphasis on customer success solutions, and at least 2+ years as a 2nd line Sales Leader.   Demonstrated ability to lead teams in selling complex, enterprise-level SaaS products, with deal sizes ranging from six to seven figures.

• Experience scaling a sales organization in a complex environment, from defining strategy to execution.

Leadership and Management

• A track record of building, coaching, and retaining top-tier sales talent.

• Strong operational skills, including expertise in pipeline management, forecasting, and CRM tools (e.g., Salesforce).

• A collaborative mindset, with the ability to work cross-functionally and align teams around shared goals.

Customer-Centric Mindset

• Deep understanding of the customer success industry and the challenges businesses face in improving retention, driving NRR, and scaling growth.

• Exceptional communication and presentation skills, with the ability to influence C-level executives and decision-makers.

• A consultative selling approach that prioritizes delivering value and building long-term partnerships.

Why You’ll Love It Here

Your job should never be a barrier to your happiness—it should be an avenue to achieve it. At Gainsight, we’re passionate about achieving our goals—at the office and everywhere—and we work every day to create an environment that nurtures our best selves.

Here are our 5 core values: 

• Golden Rule: We try to practice the Golden Rule by exercising reliability, trust and giving back to each other and our community.

• Success for All: We believe in success for our stakeholders—whether our teammates, clients, or shareholders—comes with a sincere focus on continuous learning, selfless teaching, and making a difference in each other’s lives.

• Child-like Joy: We aspire to experience child-like joy in our work and lives, injecting a spirit of passion, optimism, and laughter into everything that we do.

• Shoshin: We believe in a beginner’s mind. Don’t surround yourself with people like you--diversity breeds creativity. 

• Stay Thirsty, My Friends: We believe in a totally internally-driven strive for greatness.  The solution is to think more, not do more.

Some other reasons that Gainsters love working here:

• Our Customers: 700+ happy customers. ‘Nuff said.

• Our Pulse Community: Some of the brightest and nicest professionals, colleagues, and friends make up our 20k+ strong Pulse community.

• Our Gainsters: 1200+ (and growing!) smart and friendly teammates around the world.

• Our Pulse Impact program: We are committed to advancing an equitable, human-first industry culture by addressing professional barriers to success and promoting an inclusive community that reflects the diverse world around us.

• Our Parody Videos: No explanation needed, just watch them here!

By joining the Gainsight team, you’ll have a unique opportunity to make your mark at a high-growth company and have loads of fun doing it. Come join us!

Job Description Summary

Gainsight is seeking a dynamic Vice President of Sales to lead our high-performing sales team and drive strategic revenue growth. In this critical role, you will define and execute the sales strategy for our customer success solutions, ensuring alignment with our mission to help businesses retain customers and grow revenue through exceptional customer success practices. You will lead a talented team of sales professionals, foster cross-functional collaboration, and engage directly with C-level executives to close complex deals and build lasting partnerships.

About Us

Gainsight helps you grow your business faster and more efficiently with a single product suite that enables you to deliver value to today’s always-on customer at every moment of their journey. With Gainsight’s Customer Communities, Product Experience, Customer Success, and Customer Education products, it’s never been easier to scale your business, grow your revenue, and retain your customers.

Winning The Human Way

Leading the industry with award-winning software is rewarding. But the best moments—the ones we tell our moms about—happen when we’re together with our customers, colleagues, and partners. Our mission is to prove that you can win in business by being Human-First. For us, that means cultivating innovative ideas, nourishing a deep connection to our communities, introducing industry-defining products, and never saying no to a moment of childlike joy.