Head of Customer Support

Company Overview

Obsidian Security is a premier SaaS security platform trusted by industry leaders such as Snowflake, T-Mobile, and Algolia. With protection extended to over 200 organizations worldwide including top Fortune 1000 and Global 2000 companies, Obsidian secures critical SaaS applications like Microsoft 365 and Salesforce. Founded in 2017 with backing from premier investors including Greylock, the company specializes in reducing risk, detecting threats, and preventing breaches directly at the source. Founded by experts from CrowdStrike, Okta, Cylance, and Carbon Black, Obsidian is pioneering the evolution of SaaS security.

Amid the rise of AI in SaaS, Obsidian addresses emerging risks introduced by AI tools accessing sensitive data via integrations by uniquely monitoring OAuth token anomalies and integration exposures. The company is expanding rapidly with a growing ecosystem of partners such as SentinelOne, Databricks, and Google Cloud, and is positioned for long-term growth and IPO preparation.

Role Overview

This role is pivotal in transforming Obsidian's customer support by shifting from traditional growth based on increasing team size towards leveraging automation and agentic AI to resolve customer issues efficiently. The successful candidate will lead redesigning the support framework emphasizing technology-driven solutions over linear headcount growth, focusing on building scalable automated systems and reducing manual intervention.

Key Responsibilities

• Lead the redesign and ownership of the support operating model, prioritizing automation and agentic AI to limit dependence on expanding personnel.
• Develop, implement, and iteratively improve intelligent support systems covering all stages including triage, issue resolution, escalation, and follow-up processes.
• Create and maintain critical knowledge bases, data infrastructures, and telemetry systems that power automated solutions.
• Establish and track performance metrics such as deflection rate, automated resolution rate, cost-to-serve, average time-to-resolution, and customer satisfaction scores (CSAT) to validate model efficacy.
• Integrate support tools with product systems and customer telemetry to continuously increase automation in issue resolution.
• Collaborate closely with Product and Engineering teams to translate recurring support issues into permanent product improvements and enhanced self-service resources.
• Ensure high-quality support adhering to service level agreements (SLAs) for a technically sophisticated cybersecurity customer base throughout the transition.
• Lead and grow a focused team of support and automation engineers with a strong emphasis on technical expertise and systems innovation.

Qualifications

• Proven experience successfully implementing agentic AI or automation strategies that yield measurable decreases in manual support workload and cost-to-serve.
• Strong systems and engineering mindset with proficiency in APIs, system integrations, data pipelines, large language model (LLM) tools, and configuration of support platforms.
• Experience supporting complex technical B2B SaaS products, preferably in cybersecurity, identity management, or SaaS security sectors.
• In-depth understanding of support operations economics, including key metrics that influence cost efficiency and scalability.
• Capability to independently lead and execute the comprehensive technical roadmap for the support function.

Additional Preferred Skills

• Background as a software engineer or technical individual contributor is advantageous.
• Hands-on experience in building or integrating LLM and agent-based automation frameworks.
• Previous support engineering expertise within security or infrastructure-related products.

Role Clarification

This position is distinct from conventional people management roles focused on expanding team size proportional to ticket volume. Instead, the emphasis is on driving growth through technological innovation and strategic headcount optimization aimed at enhancing system delivery and handling complex escalations.

Employee Benefits

• Competitive salary with equity participation and 401(k) plans.
• Comprehensive medical benefits including dental and vision coverage.
• Flexible paid time off along with holidays.
• Generous parental and family leave of 12 weeks.
• Access to personal and professional growth resources.

Compensation & Employment Details

The base salary range for this role is between $165,000 and $199,000 USD. Actual salary offers will vary depending on factors such as location, skills, and experience. The role may also include equity awards and incentive compensation based on function.

Diversity & Inclusion

Obsidian Security is committed to equal opportunity employment, valuing diverse talent, passion, and empathy. Candidates will be required to verify identity and legal work eligibility. Reasonable accommodations are available upon request.