Enterprise Account Executive

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 Enterprise Account Executive to join our Sales team  reporting to the RVP, Sales Enterprise. This role is a remote role based in The United States of America.

In this role, you'll play a key role in driving enterprise revenue growth by identifying new business opportunities, managing complex sales cycles, and building lasting customer relationships through a consultative approach. This is a great opportunity for someone who thrives in a fast-paced, entrepreneurial sales environment and enjoys working cross-functionally with teams like Customer Success, Professional Services, Pre-Sales, and Product Management. The ideal candidate brings strong skills in C-suite relationship building, value-based selling, and pipeline management.

What You'll Do: 

• Achieve sales quota for assigned territory and/or accounts

• Maintain appropriate proactive sales development activity to ensure healthy pipeline management

• Execute a thorough discovery process understanding customer requirements

• Articulate value messaging related to driving customer outcomes

• Manage complex, multithreaded sales cycles across all stakeholders

• Overcome technical and business objections of prospective customers as necessary

• Conduct online or onsite product demonstrations to qualified prospects as necessary

• Respond to RFPs for qualified business opportunities where Gainsight is a fit

• Work with Gainsight’s Professional Services organization to evaluate training and consulting needs to support implementations

• Develop and maintain industry and competitive product and market knowledge

• Maintain a thorough understanding of the Gainsight product and services offered

• Gain an understanding of Gainsight’s use in the industry, as well as best practices

• Be a subject matter expert for your designated industries and territory

• Work with Business/Sales Development Representatives to define and support prospecting efforts within assigned territory

• Enter new leads, contact data, log calls and other sales information into SFDC for prospects, partners and customers

• Prepare formal proposals, produce price quotes, work with management on contract negotiations, and coordinate the gathering of all necessary paperwork to process orders

• Investigate and resolve customer problems with releases, payments, product use or implementation (as required)

• Provide feedback (customer/prospect needs, industry trends, market perceptions, competitive intelligence, etc.) to company management, Marketing and Product Management teams

• Conduct online webinars as a means of generating qualified leads 

• Plan, promote and conduct round table events in key locations within your territory

• Travel to and attend customer and prospect meetings, trade shows, conferences and round tables; 40-50% travel per year

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: 

• 5+ years of relevant experience selling Enterprise Solutions (SaaS and services) into Fortune 1000 companies and a Bachelor's degree (or equivalent combination of education and experience), required.

• Comfort and expertise calling on and presenting to C-Suite level contacts, six figure deal sizes and 6-12 month sales cycles

• Experience in the Customer Success and Product Experience fields working with key decision makers such as Chief Revenue Officers, Chief Customer Officers, leaders in Customer Success and Product Management and Marketing strategizing to drive for mutual success.
   

Nice-to-have skills:

• Proven track record of identifying business issues and creating value while managing multiple stakeholders and decision makers in a complex sales cycle

• Highly competitive, entrepreneurial and self-driven with history of quota achievement/overachievement

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 $130,000 to $150,000 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.