GTM Enablement Leader for Cybersecurity

Obsidian Security; United States; Remote; USD 180,000 - 230,000; Full time

Benefits offered by this job

Competitive compensation with equity

401k

Healthcare (dental and vision)

Flexible PTO & holidays

Gen-12 weeks new parent/family leave

Personal and professional development

Job summary

Obsidian Security is seeking a Head of GTM Enablement to own how our customer-facing teams learn, apply, and win. Lead enablement across sales, technical pre/post sale, and BDR, shrinking ramp time and improving win rates.

You will build the enablement operating system, measure impact by ramp progress and pipeline quality, and partner with Product Marketing, Product, and RevOps to stay ahead in AI security.

Qualifications

• Experience building and scaling enablement in a high-growth tech company.
• Ability to design onboarding and ramp programs for multiple roles (AE, SE, TAM, BDR).
• Fluency with AI-enabled workflows and data-driven coaching.

Responsibilities

• Build the enablement operating system with onboarding, ramp, and ongoing development.
• Sharpen field skills and deal execution through role-based training and coaching.
• Coach using real conversations and deal data to drive impact.
• Lead AI-first enablement initiatives and personalize learning paths.
• Hire and lead the enablement team and align with GTM leadership.

Skills

Enablement strategy

Onboarding design

Systemic enablement

Coaching

AI-driven enablement

Cross-functional leadership

Tools

GTM tooling

Job description

Obsidian Security is seeking a Head of GTM Enablement to own how our customer-facing teams learn, apply, and win. Lead enablement across sales, technical pre/post sale, and BDR, shrinking ramp time and improving win rates.

You will build the enablement operating system, measure impact by ramp progress and pipeline quality, and partner with Product Marketing, Product, and RevOps to stay ahead in AI security.