Sales Regional Director - Central

Gambit Security • Houston, TX

22h • Remote

About The Position

Gambit is seeking an entrepreneurial, high-performing Regional Director (RD) to lead our West Coast 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.

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.

Responsibilities

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

Benefits

• 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

What This Job Offers

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