Skilljar Account Executive

Job Description:

Join Our Team at Gainsight

Who We Are
Gainsight is not just a software company – we’re the driving force behind the Customer Success movement. Our innovative platform helps businesses keep their customers happy and successful, fueling growth and loyalty. We proudly serve hundreds of companies worldwide and have earned our reputation as “The Customer Success Company.” Our people-first approach has even been recognized on the big stage – we clinched the #1 Best Place to Work on Glassdoor in 2023. Simply put, we believe businesses can win by putting people first, and we prove it every day.

Skilljar Account Executives are responsible for identifying and creating compelling business value in selling Gainsight solutions to prospective customers. Using a consultative sales approach, the successful candidate will create and cultivate relationships to build and maintain customers for life. The Skilljar Account Executive will work with all Gainsight stakeholders including Customer Success Managers, Professional Services, Pre-Sales - Solution Consultants, Product Support and Product Management to anticipate and meet customer expectations.

What a Gainsight Skilljar Account Executive will do

Follow and manage the Gainsight Sales Process

• 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

Sales Administration

•  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; 20-40% travel per year

What we're looking for

• Bachelor's degree or equivalent experience

• Minimum of five years experience selling Enterprise Solutions (SaaS and services) into Fortune 1000 companies

• Comfort and expertise calling on and presenting to C-Suite level contacts, six figure deal sizes and 3-6 month sales cycles

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

• Demonstrated history of quota achievement/overachievement

• Someone who is highly competitive, entrepreneurial and self-driven

• 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.

Why You Belong Here
You belong at Gainsight if you want your work to matter and your workplace to spark joy and growth. Here, you’ll have the freedom to innovate, the support to grow your career, and the chance to make a real impact on thousands of businesses and their customers. We welcome talented people from all backgrounds – whether you build products, close deals, delight clients, or drive strategy, you’ll find an open door and a community that has your back. If you’re ambitious, curious, and ready to bring your whole self to work, come make your mark with us. Let’s build something special together.
At Gainsight, we empower companies to deliver exceptional customer experiences and drive sustainable growth. Our suite of solutions helps businesses connect with their customers at every stage of their journey:
Customer Success (Gainsight CS) – Tools to help customer success teams drive retention, expand relationships, and turn customers into lifelong advocates.

Relationship Intelligence (Staircase AI, by Gainsight) – Insights that enable teams to proactively strengthen customer relationships and prevent churn.

Product Experience (Gainsight PX) – Solutions that help product teams improve onboarding, drive feature adoption, and create user experiences customers love.

Customer Communities – Dynamic spaces where customers can connect, collaborate, and find the resources they need to succeed.

Customer and Partner Education (Skilljar by Gainsight) – Scalable education platforms that help companies onboard, train, and engage their customers and partners.

At every step, we help businesses create deeper connections, deliver more value, and achieve greater growth.

Our Culture
Our culture is what truly sets us apart – we believe you can win in business by being human-first and never saying no to a moment of childlike joy. That means we put people at the heart of everything we do, treating each other with empathy, embracing diversity, and having fun along the way. Five core values guide us: Golden Rule (treat others as you want to be treated), Success for All (win together), Childlike Joy (bring your inner child to work), Shoshin (beginner’s mind, always learning), and Stay Thirsty (keep aiming higher). These values aren’t just posters on a wall – we live them daily, shaping how we build products, support our customers, and celebrate our wins. At Gainsight, we work hard, laugh a lot, and lift each other up every step of the way.

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