Head of Customer Support

✨ What you’ll be working on

Obsidian Security is a SaaS security company helping organizations protect the applications and identity systems they rely on every day. Its platform is trusted by more than 200 organizations across North America, Europe, the Middle East, Southeast Asia, Australia, and New Zealand, including major Fortune 1000 and Global 2000 companies.

Founded in 2017, Obsidian was built by security leaders with experience at companies including CrowdStrike, Okta, Cylance, and Carbon Black. The company focuses on securing SaaS environments such as Microsoft 365 and Salesforce while helping businesses detect threats, reduce risk, and prevent breaches.

About the role

Obsidian Security is rethinking how technical customer support operates as the company grows. Instead of scaling support mainly by adding more people as ticket volume increases, the company wants to build a technology-led support model powered by automation and agentic AI.

As Head of Customer Support, you will lead that transformation. You will redesign the support operation so that more customer issues can be handled through automated and AI-powered systems while maintaining strong service quality for a technical cybersecurity customer base.

This is a hands-on, systems-focused leadership role. Traditional support management experience is useful, but the company is particularly interested in someone who has already built and operated technology-driven support at scale.

What you’ll do

• Own and redesign the customer support operating model around automation and agentic AI.
• Build and improve AI-powered support systems covering triage, resolution, escalation, and follow-up.
• Develop the knowledge bases, retrieval systems, data pipelines, and telemetry needed to support automation.
• Track key support metrics including deflection, automated resolution, cost-to-serve, time-to-resolution, and CSAT.
• Connect support tools with product systems, internal platforms, and customer telemetry to improve automated resolution.
• Work closely with Product and Engineering to turn recurring customer issues into product improvements and self-service solutions.
• Maintain support quality and service-level commitments throughout the transition.
• Lead a small, high-impact team focused on support engineering and automation.

What they’re looking for

• Proven experience putting AI or automation into production within a technical support environment.
• A strong technical and systems mindset, with comfort working with APIs, integrations, data pipelines, LLM tools, and support platforms.
• Experience supporting a technical B2B SaaS product.
• Cybersecurity, identity, or SaaS security experience is highly valued.
• Strong understanding of support economics, operational metrics, and cost-to-serve.
• Ability to own the technical roadmap for a support organization from strategy through execution.

What this role is not

This isn’t a traditional support leadership role focused primarily on growing a large team.

Obsidian is looking for someone who can scale support through technology, automation, and better systems rather than simply increasing headcount alongside ticket volume. Additional hiring may be needed, particularly for strategic work and tier-three escalations, but the goal is to build a support operation that becomes more efficient as it grows.

Nice to have

• Engineering or technical individual contributor experience.
• Hands-on experience building or integrating LLM or agent frameworks.
• Support engineering experience in cybersecurity or infrastructure products.

Employee benefits

US-based employees receive a competitive benefits package that includes:

• Competitive compensation, equity, and 401(k)
• Medical, dental, and vision coverage
• Flexible paid time off and paid holidays
• 12 weeks of new parent or family leave
• Personal and professional development resources

Note: This position is listed as US Remote with an East/Central time-zone preference. Candidates should confirm eligibility and location requirements with Obsidian Security before applying.