Enterprise Account Executive, Chicago

Headquarters: Remote - US

About Glean: Glean is the Work AI platform that helps everyone work smarter with AI. What began as the industry’s most advanced enterprise search has evolved into a full-scale Work AI ecosystem, powering intelligent Search, an AI Assistant, and scalable AI agents on one secure, open platform. With over 100 enterprise SaaS connectors, flexible LLM choice, and robust APIs, Glean gives organizations the infrastructure to govern, scale, and customize AI across their entire business - without vendor lock-in or costly implementation cycles. At its core, Glean is redefining how enterprises find, use, and act on knowledge. Its Enterprise Graph and Personal Knowledge Graph map the relationships between people, content, and activity, delivering deeply personalized, context-aware responses for every employee. This foundation powers Glean’s agentic capabilities - AI agents that automate real work across teams by accessing the industry’s broadest range of data: enterprise and world, structured and unstructured, historical and real-time. The result: measurable business impact through faster onboarding, hours of productivity gained each week, and smarter, safer decisions at every level. Recognized by Fast Company as one of the World’s Most Innovative Companies (Top 10, 2025), by CNBC’s Disruptor 50, Bloomberg’s AI Startups to Watch (2026), Forbes AI 50, and Gartner’s Tech Innovators in Agentic AI, Glean continues to accelerate its global impact. With customers across 50+ industries and 1,000+ employees in more than 25 countries, we’re helping the world’s largest organizations make every employee AI-fluent, and turning the superintelligent enterprise from concept into reality. If you’re excited to shape how the world works, you’ll help build systems used daily across Microsoft Teams, Zoom, ServiceNow, Zendesk, GitHub, and many more - deeply embedded where people get things done. You’ll ship agentic capabilities on an open, extensible stack, with the craft and care required for enterprise trust, as we bring Work AI to every employee, in every company. About the Role: Glean is seeking an Enterprise Account Executive for a high-impact sales role focused on driving new business and expanding relationships within large enterprise accounts. AEs at Glean are responsible for landing and managing multi-million dollar, often global, accounts by leveraging Glean’s differentiated AI technology and foundational knowledge graph to deliver tangible business outcomes for customers. You will:

• Source and close net new logos within a given territory
• Have the ability to navigate complex organizational structures and identify executive sponsors and champions
• Research and understand the business objectives of your customers and have the ability to perform a value drive sales cycle
• Collaborate with internal partners to move deals forward and ensure customer success
• You will consistently deliver ARR revenue targets and drive success through a metric based approach
• Develop and execute sales strategies and tactics to generate pipeline, drive sales opportunities and deliver repeatable and predictable bookings
• Provide timely and insightful input back to other corporate functions
• Create ROI and business justification reports based off of a data driven approach
• Run tight POCs based off of business success criteria

About you:

• 6+ years of closing experience in Sales with a track record of being a top performer
• Ability to learn, pitch and demonstrate a highly technical product and have the ability to adapt in a fast growing and changing environment
• Have clear examples of closing complex deals and selling into complex organizations
• Effectively use a repeatable method for uncovering greenfield opportunities and building out a new territory
• Previous experience building relationships and selling face to face to C level executives
• Knowledge of best of breed softwares and a technical understanding of integrations, APIs, infrastructure management, security and analytics
• Experience selling technical SaaS and cloud based software solutions
• Basic understanding of search infrastructure is a plus
• You have previous experience working with multiple teammates including SEs, BDRs, PMs, Executives & Engineers
• Experience with target account selling, solution selling, and using MEDDIC and Challenger (or similar) methodologies is a plus.

Location:

• This role is remote (must be based in Chicago)

Compensation and Benefits: The OTE range for this role is $250,000 - $300,000 annually. Compensation offered will be determined by factors such as location, level, job-related knowledge, skills, and experience. Certain roles may be eligible for variable compensation, equity, and benefits. We offer a comprehensive benefits package including competitive compensation, Medical, Vision, and Dental coverage, generous time-off policy, and the opportunity to contribute to your 401k plan to support your long-term goals. When you join, you'll receive a home office improvement stipend, as well as an annual education and wellness stipends to support your growth and wellbeing. We foster a vibrant company culture through regular events, and provide healthy lunches daily to keep you fueled and focused. We are a diverse bunch of people and we want to continue to attract and retain a diverse range of people into our organization. We're committed to an inclusive and diverse company. We do not discriminate based on gender, ethnicity, sexual orientation, religion, civil or family status, age, disability, or race. #LI-REMOTE AI-First Mindset at Glean: At Glean, AI fluency is core to how we work and we're committed to ensuring every new hire feels confident integrating AI into their everyday work. As part of the interview process, you'll complete a brief AI-focused exercise or discussion so we can understand how you think about, design, and use AI to drive impact in your role. Feel free to reference any tools, platforms, or workflows you use today — prior Glean experience isn't required. Global Data Privacy Notice for Job Candidates and Applicants: Depending on your location, the General Data Protection Regulation (GDPR), California Consumer Privacy Act (CCPA), or other privacy laws may regulate the way we manage the data of job applicants. Our full notice outlining how data will be processed as part of the application procedure for applicable locations is available in our Privacy Policy. By submitting your application, you are agreeing to our use and processing of your data as required. US applicants and their applications are subject to arbitration of disputes as outlined in our Applicant Arbitration Agreement.
By clicking “Submit Application,” I confirm that I have read the Global Data Privacy Notice and the Applicant Arbitration Agreement, and I agree to the terms.

To apply: https://weworkremotely.com/remote-jobs/glean-enterprise-account-executive-chicago