Enterprise Account Executive - CST

Gambit Security; Chicago (IL); On-site; USD 300,000 - 350,000; Full time

Benefits offered by this job

OTE with uncapped commission

Medical, dental, and vision insurance

$350 work-from-home stipend

Collaborative team and growth mindset

Job summary

Gambit Security seeks an Enterprise Account Executive to drive adoption of its Cyber Resilience platform among large enterprises. You will own the full sales cycle, articulate value to CISOs, CIOs, SecDevOps, and DevOps leaders, and help map resilience outcomes to business goals.

This is a high-impact, Series A environment where personal pipeline generation and a relentless hunter mindset are essential. You will collaborate with SEs, SDRs, and Marketing to expand territories and deliver

Qualifications

• 7+ years of enterprise sales experience with quota attainment.
• Proven track record navigating complex multi-stakeholder deals in Fortune 500.
• Experience selling to CISOs or CIOs; cybersecurity/cloud infra knowledge is a plus.
• Experience in Series A/B startups and building momentum without established brand.
• Proven ability to generate personal pipeline, not just rely on inbound.
• Familiarity with Command of the Message methodology.
• Willingness to travel as required.

Responsibilities

• Manage the full sales cycle from prospecting to close.
• Persuade technical and executive stakeholders (CISOs, CIOs, SecDevOps, DevOps leaders).
• Collaborate with SEs, SDRs, and Marketing to maximize coverage.
• Deliver predictable revenue growth and accurate forecasting.

Skills

Enterprise sales

Multi-stakeholder deals

CISO/CIO selling

Series A startup experience

Pipeline generation

Command of the Message

Travel readiness

Tools

Kubernetes

Containers

Terraform

Data backup

Job description

About Us

Gambit is the AI-native resilience platform that ensures digital continuity never expires. It unifies governance across cloud, backups, security tools, and IaC, mapping applications, identifying gaps, and validating recovery paths in real time. Gambit turns resilience assumptions into business certainty before an incident ever occurs.

The Opportunity

We are looking for a relentless, consultative Enterprise Account Executive to help accelerate our market adoption. You will be responsible for introducing our groundbreaking Cyber Resilience platform to the world’s largest enterprises. If you thrive in fast-paced Series A environments, possess strong pipeline-generation DNA, and love selling complex, highly technical solutions to executive buyers, we want to talk to you.

About The Role

• Manage the entire sales cycle: from personal pipeline generation and qualification to technical evaluation, negotiation, and closing.
• Pitch effectively to technical and executive stakeholders, specifically CISOs, CIOs, SecDevOps, and DevOps leaders.
• Collaborate closely with Sales Engineers (SEs), SDRs, and Marketing to maximize regional territory coverage.
• Deliver predictable revenue growth and maintain high forecasting accuracy.

Requirements

• 7+ years of successful enterprise sales experience, consistently exceeding quota.
• Proven track record of navigating complex, multi-stakeholder deals in the Fortune 500 space.
• Strong experience selling into the CISO or CIO suite; understanding of cybersecurity, cloud infrastructure (Kubernetes, Containers, Terraform), or data backup is a major plus.
• Experience working in Series A/B startups - you know how to create momentum where there isn't an established brand name yet.
• Expertise in driving personal pipeline generation (not relying solely on inbound or marketing).
• Preference for candidates trained in Command of the Message methodology.
• Unwavering drive, grit, and resilience.
• Ability to travel as required to close deals.

Benefits - Why Gambit?

At Gambit, we believe great work starts with great people — and we’re building a team of smart, driven, genuinely great co-workers who enjoy doing big things together.

Here’s what you can expect when you join us:

• $300,000-$350,000 OTE with uncapped commission
• Competitive medical, dental, and vision insurance
• A $350 work-from-home stipend to create a setup that helps you do your best work
• Work alongside smart, supportive, and collaborative co-workers who are excited to build something meaningful together

Pay Transparency Disclosure

Job level and actual compensation will be decided based on factors including, but not limited to, individual qualifications objectively assessed during the interview process (including skills and prior relevant experience, potential impact, and scope of role), market demands, and specific work location. The listed range is a guideline, and the range for this role may be modified. For roles that are available to be filled remotely, the pay range is localized according to employee work location.

EEO

Gambit Security is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, genetic information, or any other characteristic protected by applicable federal, state, or local law.