US Remote (East/Central) Remote (Country) Full-time USD 165,000 – 199,000 / year

Obsidian Security is hiring a Head of Customer Support

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.

Requirements

  • 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.

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.
About company
Obsidian Security
Obsidian Security builds a complete SaaS security platform to reduce risk, detect and respond to threats, and prevent breaches at the source, securing platforms like Microsoft 365, Salesforce, and hundreds more. The company focuses on securing SaaS applications in the era of agentic AI and is trusted by global enterprises including Snowflake, T-Mobile, and Pure Storage.
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Posted 2 hours ago