[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.

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