Head of GTM Enablement

About The Role

Obsidian is looking for a Head of GTM Enablement to own how our customer-facing teams learn, apply, and win. This role leads enablement across the full go-to-market motion: sales, technical (both pre and post sale), and BDR. The mandate is simple. Drive higher sales participation and faster revenue by shrinking ramp time, getting more reps into productive motion, making pipeline generation more efficient, and improving win rates.

This is not a content librarian or LMS administrator role. You will build and run the enablement operating system that turns strategy into consistent field execution, and you'll measure success in reps ramped, deals progressed, and quota attained rather than slides shipped or courses completed. You will report to leadership, be a trusted operating partner to the broader GTM leadership team, and partner closely with Product Marketing, Product, Sales Engineering, Customer Success, and RevOps to keep the field sharp as the market for AI Security evolves.

What You'll Do

Build the enablement operating system

• Own the strategy, structure, cadence, and execution of enablement across sales, technical, and BDR, covering onboarding, ramp, and ongoing development.
• Design and run onboarding and personalized, role-based ramp programs built to measurably shorten the time it takes new AEs, SEs, TAMs, and BDRs to become productive.
• Run enablement as a system with a consistent weekly, monthly, and quarterly rhythm, so the right people absorb the right knowledge at the right moment.

Sharpen field skills and deal execution

• Enable the field on the fundamentals that move deals: relevant security and product knowledge, persona-based pain discovery, new business meeting excellence (identifying use cases, bringing social proof, and quantifying pain), competitive positioning, and closing, including how to build durable champions inside accounts.
• Equip technical talent across pre and post sale to win the technical evaluation and drive successful proofs of value.
• Enable the BDR motion to generate more and better qualified pipeline.

Coach from real conversations

• Ground enablement in what is actually happening in deals.