Head of Customer Support

Obsidian Security

Head of Customer Support at Obsidian Security rethinking tech support through automation and agentic AI. Leading transition with a focus on operational excellence and measurable outcomes.

Posted 6/19/2026full-timeRemote • 🇺🇸 United StatesLead💰 $165,000 - $199,000 per yearWebsite

Tech Stack

Tools & technologies

Cyber Security

About the role

Key responsibilities & impact

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

What you’ll need

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.

Benefits

Comp & perks

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

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

agentic AIautomationAPIsdata pipelinesLLM-based toolingsupport platform configurationmetrics definitioncost-to-serve analysisdeflection rate measurementautomated resolution rate

Soft Skills

leadershipteam managementoperationalizationproblem-solvingcommunicationcollaborationstrategic thinkingexecutionadaptabilityquality maintenance