VP, Sales

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. 

We’re looking for a full-time Vice President, Sales - North America to join our sales team reporting to the Chief Revenue Officer. This is a remote role based in the United States, with a preference for candidates in the Eastern or Central time zones.

The Vice President, Sales Sales will lead the North America sales organization, overseeing a team spanning pre- and post-sales functions, including frontline sales managers, Account Executives, Solution Consultants, and Customer Account Managers. This role is accountable for driving new business, expansion, and select renewals for a multi-product portfolio, aligning closely with Marketing, Customer Success, and RevOps to execute a high-velocity, insights-driven GTM motion. The VP, Sales will build a strong leadership bench and position Gainsight at the forefront of the market shift to Revenue-as-a-Service, leveraging AI-driven customer success solutions.

• Define and execute a scalable sales strategy that drives ARR growth (net new, expansion, and renewals) across Commercial, Enterprise, and Strategic segments.

• Strengthen forecast accuracy, pipeline coverage, and rep productivity while maintaining operational excellence.

• Drive predictable, scalable growth by shifting from annual renewals to multi-year, high-value agreements.

• Take a hands-on role in high-value, complex deals, selling AI-enabled SaaS solutions to C-level executives.

• Expand wallet share in strategic accounts by leveraging Gainsight’s full portfolio of solutions.

• Lead, coach, and develop a high-performing team across multiple sales and solutions functions.

• Attract, retain, and mentor top talent, fostering a culture of collaboration, accountability, and results.

• Build leadership capability at all levels, from first-time managers to seasoned leaders.

• Establish repeatable partner-led co-sell motions with strategic partners to accelerate large, multi-product deals.

• Collaborate closely with peers across the executive team to advance company-wide growth initiatives.

• Leverage customer and competitive insights to evolve sales strategy and product positioning.

• Act as a strategic advisor to the executive team, contributing insights on market trends and customer behavior to inform broader company planning.

• Partner cross-functionally with Marketing, Product, and Customer Success to ensure alignment across the full customer lifecycle and deliver a seamless go-to-market experience.

• Champion a value-based, consultative sales approach, building long-term partnerships with customers.

This is not a complete list of responsibilities, and the scope of the role may evolve with the needs of the team and business.

• 10+ years in sales leadership roles, including at least 2+ years as a second-line leader managing multiple managers, and a Bachelors degree.

• Scaled revenue in high-growth environments, such as from $50M to $200M or from $200M to $500M+, balancing strategic vision with hands-on execution.

• Directed a $130M+ book of business, driving results across SMB, Enterprise, and Strategic segments.

• Achieved success selling to both new business and expansion accounts, with renewals experience considered a plus.

• Demonstrated success selling AI-enabled and other complex SaaS solutions to senior decision-makers.

• Inspires high-performing teams with a respected leadership presence, coaching and developing talent while balancing strategic foresight with hands-on execution, and communicating with influence and brevity at the C-suite level.

• Built operational discipline through deep expertise in forecasting, pipeline management, and data-driven sales processes.

• Makes confident decisions with imperfect information, demonstrating agility in fast-changing conditions.

• Partners closely with cross-functional peers to drive customer-centric growth initiatives.

• Understands Customer Success and recurring revenue models, including Net Revenue Retention (NRR), expansion, and churn mitigation.

• Leverages modern enterprise sales tech stacks (e.g., Salesforce, Clari, Gong, Outreach, etc.).

• Influences product and marketing strategy by sharing customer insights and field intelligence.

• Maintains flexibility to travel up to 50% of the time, typically one to two days per week.

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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 base salary range for this role is $175,000-$250,000 USD annually. This role is also eligible for commission, with on-target earnings (OTE) in the range of $350,000-$500,000 USD annually, 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.​

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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.

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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 contact [email protected]. 

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.