Enterprise Account Executive (Chicago)

Upwind Security; Chicago (IL); On-site; USD 120,000 - 180,000; Full time

Job summary

Upwind is seeking an experienced Enterprise Account Executive to drive new business with C-level executives and technical stakeholders in the Greater Chicago area. You will lead end-to-end sales cycles, develop strategic plans, and build trusted relationships with customers and channel partners to close enterprise deals.

You will partner with technical teams to ensure successful integration and deliver quantified ROI, while maintaining rigorous forecasting, pipeline management, and a data-driven

Qualifications

• Proven track record of driving and closing enterprise deals.
• Ability to sell to C-level executives and technical stakeholders in Cloud / Security / DevOps.
• Consistent achievement of quota and revenue targets with strong W2 history.
• Familiarity with qualification methodologies (e.g. MEDDPICC) and a disciplined sales process.
• Maintain accurate forecasting and reporting to leadership with data-driven SFDC hygiene.
• Excellent communication and presentation skills.

Responsibilities

• Develop and execute a comprehensive sales strategy to identify and generate new business pipeline, exceed revenue targets, and win new enterprise logos.
• Demonstrate understanding of customer needs and business objectives to position Upwind’s solution with executives and stakeholders.
• Partner with technical teams to ensure integration and time-to-value realization for clients.
• Lead end-to-end sales cycles from pipeline to ROI justification.
• Collaborate with channel partners to expand market reach and close deals.
• Lead contract negotiations to completion and closure.

Skills

Enterprise sales

C-level selling

Forecasting

Communication

Sales process

MEDDPICC

Tools

Salesforce (SFDC)

Job description

Description

Upwind is a next-generation Cloud Security Platform that leverages runtime context to identify and prioritize critical risks, providing precise insights and efficient cloud security management. Unlike traditional tools, Upwind uses runtime data proactively for risk prioritization and posture insights, ensuring teams focus on what truly matters. With industry-leading efficiency and eBPF-powered sensors, Upwind delivers comprehensive capabilities, including agentless cloud posture discovery, real-time threat protection, and integrated API security. From misconfigurations to malware defense, Upwind ensures end-to-end, cost-effective cloud infrastructure protection. At Upwind, you’ll have the opportunity to think creatively, explore new ideas, and use your skills to make a meaningful impact on our growth.

We are looking for an experienced Enterprise Account Executive to join our team of expert sellers that is deeply committed to building meaningful relationships with customers, focusing on their value and thinking strategically about bringing deals to close. This is a field sales role open to qualified candidates within the Greater Chicago area.

Responsibilities

• Develop and execute a comprehensive sales strategy to identify and generate new business pipeline, exceed revenue targets, and win new enterprise logos
• Demonstrate a thorough understanding of customer needs, challenges, and business objectives to effectively position Upwind’s solution with C-level executives and technical stakeholders
• Partner closely with technical teams to ensure seamless integration and implementation to accelerate the time-to-value realization for clients
• Lead and execute end-to-end sales cycles with excellence in all phases: from pipeline generation and opportunity qualification to the creation and delivery of a quantifiable business case / ROI justification
• Collaborate and build trusted relationships with Upwind channel partners and ecosystem to expand and optimize market reach
• Lead contract negotiations to completion and successful closure

Requirements

• Proven track record of driving and closing enterprise deals
• Ability to effectively sell to both C-level executives and technical stakeholders in Cloud / Security / DevOps
• Consistent achievement of quota and revenue targets with strong W2 history
• Familiarity and experience utilizing proven qualification methodologies (e.g. MEDDPICC) and a disciplined sales process
• Maintain accurate forecasting and reporting of the business to leadership and embrace a data-driven approach to SFDC hygiene
• Excellent communication and presentation skills.
• Self-motivated, results-driven, collaborative, and adaptable to keep up in a very fast-paced, rapidly changing, startup environment
• Strong understanding of cloud security concepts, technologies, and trends preferred