Head of Customer Support
obsidiansecurity • US Remote (East/Central)
Posted: June 18, 2026
Job Description
About the role
Obsidian Security protects organizations against threats across their SaaS and identity environments. As we scale, we are deliberately rethinking how technical support is delivered. We are not looking to grow this function by adding headcount in proportion to ticket volume. We are looking to scale it through systems, automation, and agentic AI.
This role owns that transition. You will re-architect the support operating model around technology to resolve the majority of customer issues through automated and agentic systems rather than human effort. Traditional people-management experience is welcome, but is not what we are optimizing for. We are looking for an operator who has already built and run technology-led support at scale.
What you'll do
- 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.
What we're looking for
- 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.
What this role is not
This is not a traditional people-management or org-scaling role. We are explicitly optimizing for someone who scales the function through systems and automation rather than linear headcount growth. The role has full autonomy to add headcount, but the purpose of that headcount is to improve the strategic delivery of the support model and to handle tier-three escalation management, not to absorb ticket volume. Conventional support-leadership experience is valued but secondary to demonstrated technical and automation capability.
Nice to have
- 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.
Additional Content
About the role
Obsidian Security protects organizations against threats across their SaaS and identity environments. As we scale, we are deliberately rethinking how technical support is delivered. We are not looking to grow this function by adding headcount in proportion to ticket volume. We are looking to scale it through systems, automation, and agentic AI.
This role owns that transition. You will re-architect the support operating model around technology to resolve the majority of customer issues through automated and agentic systems rather than human effort. Traditional people-management experience is welcome, but is not what we are optimizing for. We are looking for an operator who has already built and run technology-led support at scale.
What you'll do
- 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.
What we're looking for
- 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.
What this role is not
This is not a traditional people-management or org-scaling role. We are explicitly optimizing for someone who scales the function through systems and automation rather than linear headcount growth. The role has full autonomy to add headcount, but the purpose of that headcount is to improve the strategic delivery of the support model and to handle tier-three escalation management, not to absorb ticket volume. Conventional support-leadership experience is valued but secondary to demonstrated technical and automation capability.
Nice to have
- 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.