AI-Driven Customer Support Lead

Obsidian; United States; Remote; USD 165,000 - 199,000; Full time

Benefits offered by this job

Equity

401k

Healthcare (dental & vision)

PTO & holidays

Parental leave

Development resources

Job summary

Obsidian Security is redefining how technical support is delivered by leveraging agentic AI and automation to drastically reduce human effort. The role focuses on re-architecting the support operating model, building data-driven knowledge and telemetry, and delivering self-service capabilities across the lifecycle.

You will lead a small, skilled team to scale support while maintaining high standards. The ideal candidate brings a strong systems orientation, practical experience with APIs, data

Qualifications

• Demonstrated track record of operationalizing agentic AI or automation in a technical support environment, with measurable deflection and cost-to-serve outcomes.
• Strong systems and engineering orientation with experience in APIs, integrations, data pipelines, and support tooling.
• Experience supporting a technical B2B SaaS product; cybersecurity or SaaS security context preferred.
• Fluency in support economics and the metrics that govern cost-to-serve and scale.
• Ability to own and execute the technical roadmap end-to-end.

Responsibilities

• Own the support operating model and redesign it around automation and agentic AI rather than linear headcount growth.
• Design, deploy, and improve agentic support systems across triage, resolution, escalation, and follow-up.
• Build knowledge bases, retrieval systems, and the telemetry needed by these systems.
• Define metrics: deflection rate, automated resolution, cost-to-serve, time-to-resolution, CSAT.
• Integrate support tooling with product and internal systems and customer telemetry.
• Partner with Product and Engineering to convert signals into product fixes and self-service.
• Maintain support quality and SLAs for a technical cybersecurity customer base.
• Lead a small, high-leverage team of support and automation engineers.

Skills

Agentic AI

Automation

APIs

Data pipelines

LLM tooling

Support platform configuration

Job description

Obsidian Security is redefining how technical support is delivered by leveraging agentic AI and automation to drastically reduce human effort. The role focuses on re-architecting the support operating model, building data-driven knowledge and telemetry, and delivering self-service capabilities across the lifecycle.

You will lead a small, skilled team to scale support while maintaining high standards. The ideal candidate brings a strong systems orientation, practical experience with APIs, data