[Remote] Head of Customer Support

Note: The job is a remote job and is open to candidates in USA. Obsidian Security is a leading SaaS security platform that protects organizations against threats across their SaaS and identity environments. The Head of Customer Support role focuses on re-architecting the support operating model around technology, automation, and agentic AI to resolve customer issues efficiently. This position involves designing and improving support systems, integrating support tooling, and leading a small team of support engineers.ResponsibilitiesOwn the support operating model and redesign it around automation and agentic AI rather than linear headcount growthDesign, deploy, and continuously improve agentic support systems across the full lifecycle: triage, resolution, escalation, and follow-upBuild the knowledge and data infrastructure these systems depend on, including knowledge bases, retrieval systems, and the telemetry that feeds themDefine and instrument the metrics that prove the model works: deflection rate, automated resolution rate, cost-to-serve, time-to-resolution, and CSATIntegrate support tooling with the product, internal systems, and customer telemetry so that resolution becomes increasingly automated over timePartner with Product and Engineering to convert recurring support signals into product fixes and self-service capabilitiesMaintain support quality and SLAs for a technical cybersecurity customer base throughout the transitionLead a small, high-leverage team of support and automation engineers, hiring for technical and systems capabilitySkillsA demonstrated track record of operationalizing agentic AI or automation in a technical support environment, with measurable deflection and cost-to-serve outcomesA strong systems and engineering orientation. You are comfortable with APIs, integrations, data pipelines, LLM-based tooling, and support platform configurationExperience supporting a technical B2B SaaS product. Cybersecurity, identity, or SaaS security context is strongly preferredFluency in support of economics and the metrics that govern cost-to-serve and scaleThe ability to own and execute the technical roadmap for the support function end-to-endAn engineering or technical IC backgroundDirect experience building or integrating LLM and agent frameworksPrior hands-on support engineering experience in a security or infrastructure productBenefitsCompetitive compensation with equity and 401kComprehensive healthcare with dental and vision coverageFlexible paid time off and paid holiday time off12 weeks of new parent or family leavePersonal and professional development resourcesIn addition to a competitive base salary, this position is eligible for equity awards and may be eligible for sales commission or incentive compensation based on the role or function within the company.Company OverviewObsidian Security is a threat detection and posture management for business-critical saas applications. It was founded in 2017, and is headquartered in Newport Beach, California, USA, with a workforce of 51-200 employees. Its website is https://www.obsidiansecurity.com.