Enterprise Account Executive, Chicago

Glean; Chicago, Northern (IL, KY); Hybrid; USD 250,000 - 300,000; Full time

Benefits offered by this job

Medical Insurance

Vision Insurance

Dental Insurance

401k plan

Home office stipend

Education stipend

Wellness stipend

Lunch benefits

Job summary

Glean is seeking an Enterprise Account Executive for a high-impact, remote role focused on landing new logos and expanding relationships within large enterprise accounts across North America.

You will navigate complex organizations, lead multi-million dollar deals, and deliver measurable business impact by leveraging Glean’s AI-powered knowledge graph. You’ll collaborate with SEs, BDRs, PMs, and executives to drive ARR and strategic growth.

Qualifications

• 6+ years closing experience in sales, with a track record of top performance.
• Experience selling to C-level executives in complex organizations.
• Ability to learn, pitch, and demonstrate a highly technical product in a fast-growing environment.
• Knowledge of MEDDIC, Challenger, and solution selling methodologies is a plus.

Responsibilities

• Source and close net new logos within a given territory.
• Identify executive sponsors and champions in complex organizations.
• Research customer objectives and drive value through the sales cycle.
• Collaborate with internal teams to move deals forward and ensure customer success.
• Deliver ARR targets and drive predictable bookings.

Skills

Closing deals

C-level selling

SaaS sales

MEDDIC

Challenger

Executive relationships

Tech product sense

CRM proficiency

Tools

Salesforce

HubSpot

MS Excel

Job description

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

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.