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 seeking an entrepreneurial, high-performing Regional Director (RD) to lead our Central expansion. As the RD, you will initially act as a player-coach, driving your own enterprise pipeline while laying the foundation to hire, mentor, and scale your regional team of Account Executives (AEs). This is a critical leadership role in a well-funded, fast-growing Series A startup where drive, resilience, and executive presence are paramount.

About the role

• Drive & Close: Source, navigate, and close complex Enterprise SaaS deals within the Fortune 500 network, primarily selling to CISOs, CIOs, and Infrastructure leaders.
• Build the Team: Partner closely with the VP of Sales to recruit, onboard, and lead a high-performing team of Central Account Executives.
• Collaborate Cross-Functionally: Work hand-in-hand with the SE Leader, SDR teams, Marketing, and Post-Sales to build a repeatable, scalable revenue engine.
• Pipeline Generation: Own and execute a personal pipeline generation strategy while fostering a high-velocity sales culture within the region.

Requirements

• 7+ years of enterprise software sales experience, with a proven track record selling into Fortune 500 companies. 
• 3+ years of frontline leadership experience. 
• Deep experience selling to CISOs and/or CIOs (Cybersecurity or Enterprise Infrastructure background highly preferred).
• Prior experience in a Series A or B startup environment; comfortable navigating ambiguity and building from scratch.
• Strong command of structured sales methodologies (preference for Command of the Message / MEDDPICC).
• Proven ability to generate a personal pipeline with referenceable enterprise clients for back-channel checks.
• High drive, exceptional resilience, and a hands-on, collaborative mindset.
• Willingness to travel on an as-needed basis.

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:

• Competitive compensation 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.