Head of Customer Support

Obsidian Security•Spokane, WA

5h•$165,000 - $199,000

About The Position

Obsidian Security is seeking a Head of Customer Support to lead a strategic transition in how technical support is delivered. This role is focused on re-architecting the support operating model around systems, automation, and agentic AI, rather than proportional headcount growth. The goal is to resolve the majority of customer issues through automated and AI-driven systems. This is an opportunity for an operator with experience in building and running technology-led support at scale to own and execute the technical roadmap for the support function end-to-end.

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 Haves

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.

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.