Enterprise Account Executive - CST

Gambit Security•Chicago, IL

About The Position

Gambit is seeking a consultative Enterprise Account Executive to accelerate adoption of its AI-native Cyber Resilience platform among the world’s largest enterprises. The role involves selling complex technical solutions to executive and technical buyers in a fast-paced Series A environment. The Account Executive manages the full sales cycle, from generating and qualifying personal pipeline through technical evaluation, negotiation, and closing. The role works with Sales Engineers, SDRs, and Marketing to expand regional territory coverage, deliver predictable revenue growth, and maintain accurate forecasts. The position requires travel as needed to close deals.

Requirements

  • At least 7 years of successful enterprise sales experience, consistently exceeding quota.
  • Proven ability to navigate complex, multi-stakeholder deals in the Fortune 500 space.
  • Strong experience selling to the CISO or CIO suite.
  • Expertise in generating personal pipeline rather than relying solely on inbound leads or marketing.
  • Unwavering drive, grit, and resilience.

Nice To Haves

  • Understanding of cybersecurity, cloud infrastructure (including Kubernetes, containers, or Terraform), or data backup.
  • Experience working at Series A/B startups.
  • Training in the Command of the Message methodology.

Responsibilities

  • Manage the entire sales cycle, including personal pipeline generation, qualification, technical evaluation, negotiation, and closing.
  • Present the platform effectively to technical and executive stakeholders, including CISOs, CIOs, SecDevOps, and DevOps leaders.
  • Collaborate with Sales Engineers, SDRs, and Marketing to maximize regional territory coverage.
  • Deliver predictable revenue growth and maintain high forecasting accuracy.
  • Travel as required to close deals.

Benefits

  • $300,000–$350,000 OTE with uncapped commission.
  • Competitive medical, dental, and vision insurance.
  • $350 work-from-home stipend.
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