[Remote] Head of Customer Support
Note: The job is a remote job and is open to candidates in USA. Obsidian Security is a leading SaaS security platform that protects organizations against threats across their SaaS and identity environments. The Head of Customer Support role focuses on re-architecting the support operating model around technology, automation, and agentic AI to resolve customer issues efficiently. This position involves designing and improving support systems, integrating support tooling, and leading a small team of support engineers.
Responsibilities
- Own the support operating model and redesign it around automation and agentic AI rather than linear headcount growth
- Design, deploy, and continuously improve agentic support systems across the full lifecycle: triage, resolution, escalation, and follow-up
- Build the knowledge and data infrastructure these systems depend on, including knowledge bases, retrieval systems, and the telemetry that feeds them
- Define and instrument the metrics that prove the model works: deflection rate, automated resolution rate, cost-to-serve, time-to-resolution, and CSAT
- Integrate support tooling with the product, internal systems, and customer telemetry so that resolution becomes increasingly automated over time
- Partner with Product and Engineering to convert recurring support signals into product fixes and self-service capabilities
- Maintain support quality and SLAs for a technical cybersecurity customer base throughout the transition
- Lead a small, high-leverage team of support and automation engineers, hiring for technical and systems capability
Skills
- A demonstrated track record of operationalizing agentic AI or automation in a technical support environment, with measurable deflection and cost-to-serve outcomes
- A strong systems and engineering orientation. You are comfortable with APIs, integrations, data pipelines, LLM-based tooling, and support platform configuration
- Experience supporting a technical B2B SaaS product. Cybersecurity, identity, or SaaS security context is strongly preferred
- Fluency in support of economics and the metrics that govern cost-to-serve and scale
- The ability to own and execute the technical roadmap for the support function end-to-end
- 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
Benefits
- 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
- In addition to a competitive base salary, this position is eligible for equity awards and may be eligible for sales commission or incentive compensation based on the role or function within the company.
Company Overview