Head of Customer Support

DaParrot Ltd; Northern (KY); Hybrid; USD 165,000 - 199,000; Full time

Benefits offered by this job

Equity and 401k

Healthcare including dental/vision

Flexible PTO and holidays

12 weeks parental leave

Professional development

Job summary

Obsidian Security seeks a technically led Head of Support to scale our service through automation and agentic AI. You will own the operating model, design end‑to‑end processes, and partner with Product/Engineering to convert signals into product fixes and self‑service capabilities.

The role emphasizes systems engineering, API integrations, and data telemetry to drive deflection, faster resolutions, and cost efficiencies while maintaining strong SLAs for a cybersecurity customer base.

Qualifications

• Proven track record of operationalizing agentic AI or automation in a technical support setting.
• Strong systems mindset with experience in APIs, integrations, and data pipelines.
• Experience supporting a technical B2B SaaS product, preferably in cybersecurity or SaaS security.

Responsibilities

• Own the support operating model and redesign it around automation and agentic AI.
• Build and improve agentic support systems across triage, resolution, escalation, and follow-up.
• Define metrics (deflection rate, automated resolution rate, cost-to-serve) and instrument telemetry.
• Lead a small team of support and automation engineers, hiring for technical capability.

Skills

Agentic AI

Automation

APIs & integrations

LLM tooling

Support platform configuration

Technical leadership

Education

Engineering background

Tools

LLM frameworks

Data pipelines

Job description

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 NewZealand, 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—Microsoft365, 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.

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.

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.

Base Salary Range

$165,000—$199,000 USD

Equal‑Opportunity Employer Statement

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 [e-mail]

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