[All remote jobs](https://jobicy.com/jobs.md)Open role[![Obsidian Security logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/3c84d813-221.jpeg)](https://jobicy.com/company/obsidian-security.md)Remote opportunity at[Obsidian Security](https://jobicy.com/company/obsidian-security.md) # Head of Customer Support Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/obsidian-security.md)Share26 Aug 2026Published41Listing views2Application actions25 Sep 2026Apply before Opportunity details ## About this role. AI SummaryObsidian Security is hiring a Head of Customer Support to transform technical support for its B2B SaaS security platform through automation and agentic AI. The role owns the end-to-end support operating model, including AI-assisted triage, resolution, escalation, knowledge infrastructure, telemetry, and service metrics. This leader will partner closely with Product and Engineering to turn recurring customer issues into product improvements and self-service capabilities. The position leads a small technical team while prioritizing scalable systems over linear support headcount growth. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis is a senior transformation role requiring demonstrated results deploying agentic AI and automation in a technical support environment. Success depends on combining support operations, systems engineering, B2B SaaS domain knowledge, and cross-functional executive-level influence. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job medianMarket rate$182,000US market range$160k–$220k0$242k AI insightThe disclosed US yearly base-salary range is $165,000 to $199,000 USD, producing an offer median of $182,000. A competitive US market base-salary range for a Head of Technical Customer Support with AI automation, cybersecurity SaaS, and operational leadership responsibilities is estimated at $160,000 to $220,000 annually; equity and incentive compensation may be additional. ## Core skills Skills and capabilities most closely associated with this opportunity. [Technical Support Leadership](https://jobicy.com/jobs?search_keywords=Technical%20Support%20Leadership.md)[Customer Support Operations](https://jobicy.com/jobs?search_keywords=Customer%20Support%20Operations.md)[Agentic AI](https://jobicy.com/jobs?search_keywords=Agentic%20AI.md)[LLM Integration](https://jobicy.com/jobs?search_keywords=LLM%20Integration.md)[Support Automation](https://jobicy.com/jobs?search_keywords=Support%20Automation.md)[B2B SaaS](https://jobicy.com/jobs?search_keywords=B2B%20SaaS.md)[Cybersecurity](https://jobicy.com/jobs?search_keywords=Cybersecurity.md)[Knowledge Management](https://jobicy.com/jobs?search_keywords=Knowledge%20Management.md)[API Integrations](https://jobicy.com/jobs?search_keywords=API%20Integrations.md)[Support Analytics](https://jobicy.com/jobs?search_keywords=Support%20Analytics.md) Sample interview questionsDescribe a support automation or agentic AI program you built and the measurable business outcomes it produced.I would outline the initial support bottleneck, the workflows automated, and the systems integrated, such as the CRM, support platform, knowledge base, and product telemetry. I would quantify outcomes including automated resolution rate, ticket deflection, reduced time-to-resolution, CSAT impact, and cost-to-serve improvement, while explaining the governance used to protect quality and escalation paths. How would you determine which customer issues are appropriate for agentic resolution versus human escalation? I would segment issues by risk, repeatability, data quality, customer impact, and required technical judgment. High-volume, low-risk, well-documented requests are strong candidates for automation, while security-sensitive, ambiguous, or high-severity incidents should have controlled escalation paths with human review and complete auditability. How would you build the knowledge and telemetry foundation for an AI-led support model? I would establish governed knowledge sources, structured product documentation, support-case taxonomies, and retrieval quality standards. I would connect these sources to ticket, product-usage, and incident telemetry, then continuously evaluate answer accuracy, containment, escalation reasons, and knowledge gaps to improve the system. What metrics would you use to demonstrate that the new support operating model is successful? I would track deflection rate, automated resolution rate, first-contact resolution, time-to-resolution, SLA attainment, reopen rate, escalation rate, CSAT, and cost-to-serve. I would pair these with quality measures such as AI answer accuracy, incident severity handling, and the rate at which recurring issues are eliminated through product or self-service changes. How would you work with Product and Engineering when recurring support issues indicate a product problem? I would provide a prioritized, evidence-based feedback loop that links issue volume, customer impact, revenue or retention risk, telemetry, and root-cause findings. Together, we would decide whether the appropriate fix is a product change, improved observability, documentation, workflow automation, or a new self-service capability, then measure the reduction in future demand. 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 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. Employee Benefits Our competitive benefits packages are designed to support our employees’ well-being, both at work and at home. Our US based employees enjoy: * 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 For more details on our US benefits, or for information on our international benefits, please see [here](https://app.rippling.com/benefits/preview/76xr7qaxl1xvkd3z). Pay Transparancy Please note that the base pay range is a guideline and for candidates who receive an offer, the base pay will vary based on factors such as work location, as well as the knowledge, skills and experience of the candidate. In 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. At Obsidian, we are proud to be an equal-opportunity employer. We value diversity and hire for talent, passion, and compassion. In compliance with federal law, all persons hired will be required to submit satisfactory proof of identity and legal authorization. If you have a need that requires accommodation, please contact accommodations@obsidiansecurity.com Information collected and processed as part of any job applications you choose to submit is subject to Obsidian’s [Applicant Privacy Policy](https://www.obsidiansecurity.com/privacy-policy/). Base Salary Range $165,000—$199,000 USD Show more [Apply now >](https://jobicy.com/jobs/151667-head-of-customer-support-2.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. 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