Head of GTM Enablement

# Head of GTM Enablement Obsidian Security On-site United States Product & Operations Posted Sep 25, 2026
• Obsidian Security is the leading SaaS security platform, trusted by global enterprises like Snowflake, T-Mobile, and Algolia. We protect 200+ organizations across North  
• America, Europe, the Middle East, Southeast  
• Asia, Australia, and New Zealand, including many of the world’s largest Fortune 1000 and Global 2000 companies.
Founded in 2017 and backed by top investors like Greylock, Obsidian was built to close a critical gap: securing SaaS apps where business happens—Microsoft 365, Salesforce, and hundreds more. The company does this by offering a complete SaaS security platform to reduce risk, detect and respond to threats, and prevent breaches at the source. Obsidian was built by leaders who redefined endpoint and identity security at Crowd Strike, Okta, Cylance, and Carbon Black.

Now, they’re transforming how SaaS is secured.
With AI driving rapid SaaS growth and complexity, agentic AI tools gain privileged access to sensitive data through integrations, creating new risks most security tools miss. Obsidian uniquely detects anomalous OAuth token activity and manages integration risks. Major announcements are on the horizon. Recognizing that SaaS security needs to evolve, Obsidian enables growing organizations to start with a lightweight, prevention-focused browser extension and expand coverage over time.
With global momentum, a growing partner ecosystem including Sentinel One, Databricks, and Google Cloud, and a major fundraise ahead, 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 Rev Ops 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.
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