Head of AI-Driven Customer Support Operations

United States Digital Space LLC; United States; Remote; USD 165,000 - 199,000; Full time

Benefits offered by this job

Health insurance

401k

Paid time off

Parental leave

Development resources

Job summary

Obsidian is seeking an operator who has built and run technology-led support at scale, re-architecting the support model around automation and agentic AI. You will own the transition and drive it end-to-end with a focus on automation-driven outcomes.

You will lead a small, high-leverage team of support and automation engineers, partner with Product and Engineering to turn signals into product fixes and self-service capabilities, and ensure SLAs for a technical cybersecurity customer base during

Qualifications

• Track record of operationalizing agentic AI or automation in a technical support environment.
• Strong systems orientation; comfortable with APIs, data pipelines, and support platform configuration.
• Experience supporting a technical B2B SaaS product, preferably cybersecurity or SaaS security.

Responsibilities

• Own the support operating model and redesign it around automation and agentic AI.
• Design and deploy agentic support systems across triage, resolution, escalation, and follow-up.
• Build knowledge bases and data infrastructure these systems depend on.

Skills

Automation in support

Agentic AI

APIs

LLM tooling

Support platform

Tools

LLM frameworks

Automation tooling

Job description

Obsidian is seeking an operator who has built and run technology-led support at scale, re-architecting the support model around automation and agentic AI. You will own the transition and drive it end-to-end with a focus on automation-driven outcomes.

You will lead a small, high-leverage team of support and automation engineers, partner with Product and Engineering to turn signals into product fixes and self-service capabilities, and ensure SLAs for a technical cybersecurity customer base during