Head of AI-Driven Support & Automation

DaParrot Ltd; Northern (KY); Hybrid; USD 165,000 - 199,000; Full time

Benefits offered by this job

Equity and 401k

Healthcare including dental/vision

Flexible PTO and holidays

12 weeks parental leave

Professional development

Job summary

Obsidian Security seeks a technically led Head of Support to scale our service through automation and agentic AI. You will own the operating model, design end‑to‑end processes, and partner with Product/Engineering to convert signals into product fixes and self‑service capabilities.

The role emphasizes systems engineering, API integrations, and data telemetry to drive deflection, faster resolutions, and cost efficiencies while maintaining strong SLAs for a cybersecurity customer base.

Qualifications

• Proven track record of operationalizing agentic AI or automation in a technical support setting.
• Strong systems mindset with experience in APIs, integrations, and data pipelines.
• Experience supporting a technical B2B SaaS product, preferably in cybersecurity or SaaS security.

Responsibilities

• Own the support operating model and redesign it around automation and agentic AI.
• Build and improve agentic support systems across triage, resolution, escalation, and follow-up.
• Define metrics (deflection rate, automated resolution rate, cost-to-serve) and instrument telemetry.
• Lead a small team of support and automation engineers, hiring for technical capability.

Skills

Agentic AI

Automation

APIs & integrations

LLM tooling

Support platform configuration

Technical leadership

Education

Engineering background

Tools

LLM frameworks

Data pipelines

Job description

Obsidian Security seeks a technically led Head of Support to scale our service through automation and agentic AI. You will own the operating model, design end‑to‑end processes, and partner with Product/Engineering to convert signals into product fixes and self‑service capabilities.

The role emphasizes systems engineering, API integrations, and data telemetry to drive deflection, faster resolutions, and cost efficiencies while maintaining strong SLAs for a cybersecurity customer base.