or apply directly on Obsidian Security's site. We never take the application ourselves.
Is this posting real?
- This role has been open
- 80 days Obsidian Security's roles stay open a median of 80 days
- Reposted
- No
- Salary listed
- No 0% of Obsidian Security's roles list one
- Ghost-job risk at Obsidian Security
- high 25 stale, 0 reposted of 25 open
- Hiring momentum
- 43 roles opened in the last 90 days ↑ up vs. the prior 90 days
- Last confirmed on the employer's board
- 2026-10-22
Measured from postings appearing on and disappearing from Obsidian Security's own greenhouse board since 2026-08-03. Full hiring picture for Obsidian Security.
About this role
The Head of GTM Enablement at Obsidian Security will lead the enablement efforts for customer-facing teams, focusing on sales, technical, and BDR functions. This role involves building and executing a comprehensive enablement operating system, designing onboarding programs, and coaching teams based on real deal data. The goal is to enhance sales participation, reduce ramp time, and improve overall win rates through effective training and alignment with various departments.
- benefits
- 3/5
- freshness
- 1/5
- career value
- 4/5
- role clarity
- 5/5
- pay transparency
- 0/5
Scored from the posting itself — how clearly the role is described, how much it says about pay and benefits, and how recently it was listed. Not a judgement of Obsidian Security as an employer.
What you need
- Experience building and scaling a GTM or revenue enablement function in a high-growth technology company
- Deep experience enabling customer-facing organizations including AEs, technical pre and post sale, and BDR teams
- Fluency in modern sales methodologies such as MEDDIC or MEDDPICC
- Metrics-driven approach with the ability to set baselines and manage to indicators
- Proven leadership skills in hiring, developing, and retaining enablement talent
- Strong program management skills with a track record of timely execution
Nice to have
- Knowledge of the cybersecurity industry and understanding of the security buyer
- Experience with AI-driven workflows in enablement
What you get
- Competitive compensation with equity and 401k
- Comprehensive healthcare with dental and vision coverage
- Flexible paid time off and paid holiday time off
- 12 weeks of new parent or family leave
- Personal and professional development resources
Worth weighing
- No specific mention of remote work flexibility beyond being remote in the US
- The role emphasizes metrics and outcomes over traditional training methods, which may not suit all candidates
- The position requires a proactive approach to enablement, which may involve significant initiative and self-direction
Summarised from Obsidian Security's posting. Read the full original.
Listed by Obsidian Security on their greenhouse job board, last confirmed open on 2026-10-22. PitchMeAI is not the employer.
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