RVP, Strategic Accounts

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 RVP, Strategic Accounts to join the Sales team  reporting to the Senior Vice President, Sales. This role is a remote role based in the USA. 

In this role, you'll play a key role in driving Gainsight's enterprise growth by leading a team of Strategic Account Executives to land major new logos, expand multi-product footprint, and build long-term platform relationships with the world's largest companies. This is a great opportunity for someone who thrives in a high-velocity, competitive enterprise sales environment and enjoys working cross-functionally with teams like Customer Success, Solution Consulting, RevOps, and Marketing. The ideal candidate brings strong skills in new business acquisition, executive relationship building, and data-driven pipeline and forecast management.

What You'll Do: 

• Own and deliver the strategic segment’s annual bookings plan, with primary emphasis on new logo acquisition, competitive displacement, and multi-product expansion into the world’s largest enterprise accounts

• Build and lead a team of Strategic Account Executives focused on winning new business, recruiting, coaching, and developing sellers who thrive on opening new relationships, closing complex deals, and growing Gainsight’s footprint

• Drive pipeline generation and maintain strong forward-looking coverage across the team, setting the pace for outbound prospecting, account-based engagement, and executive relationship development

• Personally engage as an executive sponsor on the largest and most complex opportunities, including C-level prospecting, deal strategy, competitive positioning, and negotiation on high-value transactions

• Build and execute account-level strategic plans for every named account, identifying whitespace, mapping decision-makers, positioning against competitors, and connecting the full Gainsight portfolio to customer priorities

• Orchestrate multi-product selling across Gainsight’s solution portfolio including customer success, community, education, AI agents, and conversational intelligence to land larger initial deals and drive platform-level adoption

• Collaborate cross-functionally with Customer Success, Solution Consulting, RevOps, Product, Marketing, and Professional Services to accelerate deal cycles, ensure strong post-sale handoffs, and deliver customer outcomes that fuel expansion and advocacy

• Manage the full commercial lifecycle for your segment, including renewals, ensuring the team protects revenue while staying focused on growth

• Deliver accurate, rigorous forecasts through structured deal reviews and pipeline inspection, providing clear visibility to senior leadership on segment performance, risks, and opportunities

• Attract, retain, and develop top sales talent, building a team culture where high performers are recognized, coached, and challenged to grow

This role requires travel (~40%) for customer meetings, executive briefings, team events, and company onsites. 

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

What We're Looking For: 

Must-have skills or experience:

• 10+ years of enterprise SaaS sales experience with at least 5 years of sales management experience leading teams of Enterprise Account Executives.

• Consistent track record of meeting or exceeding bookings targets, with a strong emphasis on new logo acquisition and winning in competitive enterprise environments.

• Proven ability to build and lead high-performing sales teams creating pipeline, opening new accounts, securing renewals and closing large deals.

• Proven experience owning retention outcomes for high-value enterprise accounts

• Experience leading multi-product sales motions across a portfolio of solutions, 

• Demonstrated ability to personally engage in and close complex, high-value enterprise deals involving multiple stakeholders, long sales cycles, and executive-level relationships

• Brings disciplined operating practices around pipeline generation, forecasting, and performance management in a data-driven sales culture. 

Nice-to-have skills or experience:

• Experience adopting and leveraging AI to improve productivity gains and efficiency for deal development, internal communications and operational rigor.

• Experience operating in a PE-backed B2B SaaS environment

• Familiarity with the Customer Success platform landscape and the competitive dynamics in post-sale enterprise software

• Comfort articulating the value of AI and intelligent automation to executive stakeholders 

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 $200,000 - $215,000 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 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.