Note: The job is a remote job and is open to candidates in USA. Obsidian Security is the leading SaaS security platform, trusted by global enterprises like Snowflake, T-Mobile, and Algolia. The Head of Customer Support will re-architect the support operating model around technology, focusing on automation and agentic AI to resolve customer issues efficiently. This role involves leading a team, designing support systems, and integrating tools to enhance service delivery.
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
Skills
- 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
- 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
Benefits
- 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
- Equity awards
- May be eligible for sales commission or incentive compensation based on the role or function within the company
Company Overview