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 Customer Support at Obsidian Security will lead the transition to a technology-driven support model, focusing on automation and agentic AI to resolve customer issues. This role involves redesigning the support operating model, building necessary infrastructure, and integrating support tools with product systems. The position requires a strong background in operationalizing automation within technical support environments, while maintaining service quality and metrics throughout the transition.
- benefits
- 3/5
- freshness
- 1/5
- career value
- 4/5
- role clarity
- 4/5
- 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
- Demonstrated track record of operationalizing agentic AI or automation in a technical support environment
- Strong systems and engineering orientation, comfortable with APIs, integrations, data pipelines, and support platform configuration
- Experience supporting a technical B2B SaaS product, preferably in cybersecurity or SaaS security
- Fluency in support economics and metrics governing cost-to-serve and scale
- Ability to own and execute the technical roadmap for the support function end-to-end
Nice to have
- An engineering or technical IC background
- Direct experience building or integrating LLM and agent frameworks
- Prior hands-on support engineering experience in a security or infrastructure product
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 salary listed in the main job description, but a range is provided separately
- Role emphasizes automation over traditional people management, which may not suit all candidates
- Experience in cybersecurity or SaaS security context is strongly preferred, which may limit candidates without this background
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.
More roles at Obsidian Security
- Enterprise Account Executive - CentralUS Remote (Central)
- Software Engineer - AI Security ProductPalo Alto, California, USA
- Staff IT Systems EngineerPalo Alto, CA
- Enterprise Account Executive - UKLondon, UK
- Enterprise Account Executive - San Francisco Bay AreaPalo Alto, CA
- Senior Support EngineerUS Remote (East/Central)
- Head of GTM EnablementRemote - US
- Sr Channel Account Manager (EMEA)UK - Remote