Head of Customer Support
Obsidian Security is the leading SaaS security platform, trusted by global enterprises like Snowflake, T-Mobile, and Algolia. We protect 200+ organizations across North America, Europe, the Middle East, Southeast Asia, Australia, and New Zealand, including many of the world’s largest Fortune 1000 and Global 2000 companies. Founded in 2017 and backed by top investors like Greylock, Obsidian was built to close a critical gap: securing SaaS apps where business happens—Microsoft 365, Salesforce, and hundreds more. The company does this by offering a complete SaaS security platform to reduce risk, detect and respond to threats, and prevent breaches at the source. Obsidian was built by leaders who redefined endpoint and identity security at CrowdStrike, Okta, Cylance, and Carbon Black. Now, they’re transforming how SaaS is secured. With AI driving rapid SaaS growth and complexity, agentic AI tools gain privileged access to sensitive data through integrations, creating new risks most security tools miss. Obsidian uniquely detects anomalous OAuth token activity and manages integration risks. Major announcements are on the horizon. Recognizing that SaaS security needs to evolve, Obsidian enables growing organizations to start with a lightweight, prevention-focused browser extension and expand coverage over time. With global momentum, a growing partner ecosystem including SentinelOne, Databricks, and Google Cloud, and a major fundraise ahead, Obsidian is scaling rapidly toward long-term growth and IPO readiness.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 ti...