Enterprise Account Executive, Chicago

Enterprise Account Executive: Chicago 

We are seeking a high-performing Enterprise Account Executive to lead enterprise sales efforts within the Chicago/North Central US region, targeting large enterprise organizations above 2,000 employees. This is a pivotal role requiring a strong work ethic, relentless drive, and purposeful daily activity to build and maintain a robust pipeline and exceed revenue targets.

The ideal candidate thrives in a fast-paced, high-output environment, demonstrates ownership of their territory, and executes with precision and urgency. This individual will collaborate closely with senior sales leadership, channel partners, and cross-functional teams to drive value-based sales engagements that solve complex IT and security challenges for major customers.

Key Responsibilities

• Develop and execute a comprehensive regional strategy designed to deliver a 4x pipeline relative to quota.
• Operate with a bias for action and a focus on measurable outcomes, holding yourself accountable to activity goals and performance benchmarks.
• Build and nurture strong channel and security/IT vendor partnerships, leveraging their reach and influence to accelerate growth.
• Qualify and advance opportunities using value-based selling methodologies and frameworks such as MEDDPIC, ensuring clear business value alignment with customer needs.
• Maintain high-quality hygiene in Salesforce and Clari, including:
• Consistent and insightful Chatter posts
• Clear, strategic next steps for all active opportunities
• Up-to-date MEDDPIC criteria
• Accurate and timely forecasting with realistic close dates

Minimum Qualifications

• 7+ years of success in a closing role selling to Enterprise accounts, with a proven hunter mentality and consistent quota attainment.
• Experience managing and closing complex, multi-stakeholder sales cycles within large organizations.
• Demonstrated ability to build and execute a regional go-to-market strategy, coordinating effectively with channel partners, tech alliances, BDRs, SEs, Marketing, and Product.
• Strong working knowledge of enterprise IT and security environments, including solutions like endpoint protection, vulnerability management, SIEM, CMDB, Active Directory, firewalls, cloud platforms, and SaaS offerings.

Preferred Qualifications

• Strong negotiation skills with a history of driving value-based deals and minimizing discounting.
• Highly self-motivated and proactive, with the ability to work independently and efficiently in a remote, field-based environment.
• A disciplined operator who understands the importance of CRM hygiene, structured deal execution, and precision in forecasting.
• Demonstrates a strong work ethic, integrity, and a commitment to excellence in every customer interaction.
• Competitive spirit and a deep drive to win, not just against quota, but in delivering transformational outcomes for customers.
• Strategic thinker with resourcefulness and the ability to adapt and thrive in dynamic, fast-evolving conditions.

This is more than a sales job, this is a high-impact role for someone ready to own their business, execute at a high level, and be a key contributor to the company’s growth in a top-tier market.

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