Enterprise Account Executive, Chicago

About This Opportunity

We are representing a confidential enterprise AI technology company in their search for an Enterprise Account Executive based in Chicago. Our client is a rapidly growing organization that has developed a sophisticated platform used by over 100 major enterprises across 50+ industries worldwide.

This is a high-impact sales role focused on landing new enterprise logos and building strategic relationships with Fortune 1000 accounts. You'll be selling transformative technology that integrates deeply into how large organizations access and leverage their knowledge and data.

Responsibilities

• Source and close net new enterprise accounts within your assigned territory, managing complex, multi-million dollar sales cycles
• Navigate sophisticated organizational structures to identify executive sponsors, champions, and key decision-makers
• Research customer business objectives and execute value-driven sales cycles that demonstrate measurable ROI
• Collaborate with Solutions Engineers, Business Development Representatives, Product Managers, and executive stakeholders to advance opportunities
• Consistently deliver against ARR revenue targets through a metrics-based approach
• Develop and execute territory strategies to build pipeline, drive opportunities, and deliver predictable bookings
• Create data-driven business justification and ROI analyses for enterprise buyers
• Manage tight proof-of-concept processes aligned to customer success criteria
• Provide strategic market feedback to internal product and go-to-market teams

What We're Looking For

• 6+ years of enterprise sales closing experience with a proven track record as a top performer
• Demonstrated success closing complex deals into large, matrixed organizations
• Ability to learn, pitch, and demonstrate highly technical products in fast-changing environments
• Experience building greenfield territories and uncovering new opportunities using repeatable methodologies
• Strong track record of face-to-face selling and relationship building with C-level executives
• Knowledge of enterprise software ecosystems including integrations, APIs, infrastructure, security, and analytics
• Experience selling technical SaaS and cloud-based solutions at the enterprise level
• Familiarity with solution selling frameworks such as MEDDIC, Challenger, or similar methodologies (preferred)
• Understanding of search infrastructure or enterprise knowledge management (a plus)
• Must be based in or willing to relocate to Chicago (this is a remote role with local territory focus)

How We Work With You

When you apply through Get A Job.ai, our recruiting team will review your background and schedule an initial screening call. We'll discuss your enterprise sales experience, approach to complex deals, and alignment with this opportunity. If there's a strong match, we'll submit your profile to our client for consideration and guide you through their interview process.

Important: Please apply exclusively through Get A Job.ai. Do not contact the client company directly, as all candidate submissions are managed through our talent team.

Pay

The target on-target earnings (OTE) for this role is $250,000 - $300,000 annually, consisting of base salary plus variable commission. Our client offers comprehensive benefits including medical, vision, and dental coverage, generous PTO, 401(k), home office stipend, and professional development support.

Get A Job.ai is an equal opportunity recruiting firm. We welcome applications from candidates of all backgrounds and do not discriminate based on gender, ethnicity, sexual orientation, religion, civil or family status, age, disability, or race.