Account Executive | Enterprise | North Central

Cast AI • Chicago, IL

1d • Remote

About The Position

Cast AI is hiring an Account Executive to develop new business across the North Central US. This is a pure new-logo role: the Account Executive will own a large territory, prioritize target accounts, generate their own pipeline, and manage opportunities from first conversation through negotiation and close. The role is not focused on growing existing accounts.

The Americas sales team is growing under new sales leadership, and people joining now will help shape how Cast AI sells across the region. The Account Executive will work with Sales Engineering, Customer Success, and Marketing to advance deals and ensure customers realize the value of the product. The position is based in the US North Central region and operates in a flexible, remote-first global environment.

Cast AI is an automation platform for cloud-native and AI infrastructure. It embeds autonomous decision-making into Kubernetes and cloud environments to continuously optimize production performance, reliability, and efficiency. The company reports serving more than 2,100 companies and operating across 34 countries.

Requirements

• Proven success winning new logos in B2B SaaS; experience must include hunting rather than only managing existing accounts.
• History of meeting or exceeding quota, with attainment figures the candidate can discuss.
• Demonstrated ownership of pipeline generation and a consistent weekly prospecting rhythm.
• Experience running deals using MEDDPICC or another structured sales qualification methodology.
• Experience selling technical products, such as cloud infrastructure, DevOps, observability, platform engineering, or data, and translating them into clear business ROI.
• Success navigating complex deals involving multiple technical and financial stakeholders.
• Strong territory-planning skills, including identifying suitable accounts in a large territory and prioritizing effectively.
• Willingness to learn a new product quickly, receive feedback on sales pitches, and iterate.
• Based in the US North Central region.

Nice To Haves

• Experience with Kubernetes, cloud cost optimization, or the cloud-native ecosystem.
• Experience selling to software-first, digital-native companies with large cloud bills, including customers in commercial or mid-market segments.
• Experience at a company with a strong sales playbook and enablement culture, ideally during an earlier high-growth hunting phase.

Responsibilities

• Build and source a pipeline independently, maintaining a regular prospecting rhythm and dedicating significant weekly time to outbound activity.
• Prioritize a large territory by identifying and focusing on the highest-fit target accounts.
• Win new customers end to end, from initial conversation through negotiation and close.
• Run disciplined sales opportunities, including opportunity assessment, value discovery, value demonstration, and mutual close plans.
• Build relationships with multiple stakeholders, including CTOs, VPs of Engineering, FinOps, Finance, and Procurement, and develop champions within accounts.
• Develop account-specific business cases and ROI narratives based on cloud spend and engineering maturity.
• Maintain accurate forecasts and clean CRM records, and confidently present pipeline reviews to leadership.
• Partner with Sales Engineering, Customer Success, and Marketing to advance deals and help customers realize the value they purchased.

Benefits

• 401(k) retirement plan with a 100% company match on employee contributions up to 6% of pay, available after three months of employment.
• UnitedHealthcare medical, dental, and vision coverage.
• Equity options.
• Learning budget for professional and personal growth.
• Team-building budget and company events.
• Equipment budget.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed