Head of Customer Support

Company Overview

Obsidian Security is a SaaS security platform used by enterprise customers worldwide, including well-known organizations such as Snowflake, T-Mobile, and Algolia. The company protects more than 200 organizations across North America, Europe, the Middle East, Southeast Asia, Australia, and New Zealand, and serves many Fortune 1000 and Global 2000 businesses.

Established in 2017 and supported by investors including Greylock, Obsidian set out to address a major gap in SaaS protection: securing the applications where core business operations take place, such as Microsoft 365 and Salesforce. Its platform is designed to lower risk, identify and respond to threats, and stop breaches before they start. The leadership team includes veterans who helped shape endpoint and identity security at companies such as CrowdStrike, Okta, Cylance, and Carbon Black.

As AI accelerates SaaS expansion and complexity, new exposure is created through integrations and privileged access to sensitive information. Obsidian focuses on identifying abnormal OAuth token behavior and managing integration-related risk. The business is growing quickly, has a strong partner ecosystem that includes SentinelOne, Databricks, and Google Cloud, and is moving toward a major fundraise and long-term public-market readiness.

Role Summary

This position owns the next evolution of technical customer support at Obsidian Security. The company is intentionally shifting support away from a model that scales only by adding more people. Instead, the goal is to build a support organization powered by systems, automation, and agentic AI.

The selected leader will redesign the support operating model so that most customer issues are resolved through automated and agent-driven workflows rather than manual intervention. Prior people leadership experience is welcome, but the core requirement is proven success in building and running technology-led support at scale.

What You Will Do

• Take ownership of the support operating model and reshape it so automation and agentic AI drive scale instead of linear hiring.
• Design, launch, and refine end-to-end agentic support workflows covering triage, resolution, escalation, and follow-up.
• Develop the knowledge and data foundations that support automation, including documentation systems, retrieval layers, and telemetry inputs.
• Set up and track the operating metrics that show whether the model is working, such as deflection rate, automated resolution rate, cost to serve, resolution time, and CSAT.
• Connect support tools with product systems, internal platforms, and customer telemetry so more issues can be resolved automatically over time.
• Work with Product and Engineering to turn repeated support patterns into product improvements and self-service options.
• Preserve service quality and SLA performance for a technically sophisticated cybersecurity customer base during the transition.
• Guide a lean, high-impact team of support and automation engineers, with hiring focused on technical depth and systems thinking.

What We Are Looking For

• Proven experience putting agentic AI or automation into practice within a technical support environment, with clear gains in deflection and cost efficiency.
• A strong engineering mindset and comfort working with APIs, integrations, data flows, LLM-based tools, and support platform setup.
• Background supporting a technical B2B SaaS product; experience in cybersecurity, identity, or SaaS security is especially valuable.
• Understanding of support economics and the metrics used to manage cost to serve and operational scale.
• Ability to own the support technology roadmap and drive execution from start to finish.

What This Role Is Not

This is not a conventional support leadership position focused mainly on managing a growing headcount. The emphasis is on scaling through automation and systems rather than expanding the team in direct proportion to ticket volume. The role does allow the addition of headcount when needed, but that hiring is meant to strengthen the support model strategically and manage tier-three escalations, not to simply absorb more tickets. Traditional support management experience is useful, but it is secondary to demonstrated technical and automation expertise.

Nice to Have

• An engineering background or prior experience as a technical individual contributor.
• Hands-on experience creating or integrating LLM and agent frameworks.
• Experience building or supporting infrastructure or security products in a hands-on support engineering capacity.

Benefits

Employees in the US receive a competitive benefits package designed to support well-being at work and at home. Benefits include competitive compensation with equity and a 401(k), full healthcare coverage with dental and vision, flexible paid time off plus paid holidays, 12 weeks of new parent or family leave, and resources for personal and professional growth.

Equal Opportunity and Compliance

The company is an equal opportunity employer and hires based on talent, passion, and compassion. Candidates who receive an offer must provide proof of identity and legal work authorization in accordance with federal law. If an accommodation is needed, candidates may contact the company directly. Any information submitted during the application process is handled according to the company’s applicant privacy policy.

Compensation

The base salary range for this role is $165,000 to $199,000 per year. The final offer may vary depending on work location and the candidate’s experience, skills, and knowledge. In addition to base pay, the role is eligible for equity awards and may also include sales commission or incentive compensation depending on the function.