Head of GTM Enablement

Obsidian Security · Remote - US

  • Senior
  • Full-time
  • $180,000 – $230,000
  • Posted 2026-07-10
  • Confirmed live on 25 September 2026

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Job description

Obsidian Security is a global leader in cyber security protecting the SaaS and non-human identity layer modern enterprises run on — from Salesforce and Snowflake to the AI agents now deployed inside them. The Obsidian Security platform gives unified visibility into every human and machine identity, app, and integration across their SaaS estate, detects identity-based and supply chain attacks in real time, and enforces least-privilege access before it's exploited. Trusted by major Fortune 500 companies T-Mobile, Workday, Snowflake, and S&P Global, Obsidian ranked No. 95 on the 2025 Deloitte Technology Fast 500™, growing nearly 1000% from 2021–2024 — helping CISOs turn an unmonitored attack surface into one they can govern with confidence. Obsidian has also been recognized by Forbes as America's Best Startup Employers in 2026.

In August 2026, Obsidian raised $85 million in Series D financing led by Crescent Cove Advisors, with participation from existing investors including Greylock Partners, Menlo Ventures, Norwest Venture Partners, IVP, Wing Ventures, and GV — pushing Obsidian's valuation to $1.1 billion, crossing into unicorn status. Obsidian is using the funding to deepen its R&D in agentic AI security and extend its platform as the standard for governing what AI agents can access and do inside third-party applications.

With global momentum, a growing partner ecosystem including SentinelOne, Databricks, and Google Cloud, and fresh capital from its Series D behind it, Obsidian is scaling rapidly toward long-term growth and IPO readiness.

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. Use call intelligence such as Gong and real customer conversations, rather than certification pass rates or content engagement dashboards, as your primary signal for what is working, where reps are stuck, and what to coach next.

• Turn those observations into specific coaching and interventions, and coach the frontline leaders so they reinforce the same behaviors.

Work AI first

• Bring fluency in AI-driven workflows to make enablement faster and more efficient, and to systematize routine practices instead of doing them by hand.

• Use AI and performance data to build personalized enablement tracks that meet each rep where they are, instead of one size fits all training.

Lead the function

• Hire, develop, and lead the enablement team, and set the standard by leading from the front.

• Drive cross-functional alignment proactively, anticipating what the field will need and getting ahead of it rather than reacting to inbound requests, and hold partners to clear commitments.

• Bring strong program management: named owners, clear timelines, refresh cadences, and follow through.

How You'll Be Measured

We measure enablement on outcomes, not activity. Your primary indicators are:

• Ramp time: how quickly new reps rea

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