Senior Support Engineer

✨ What you’ll be working on

Obsidian Security is a SaaS security company helping organizations protect the applications and identity systems they depend on. 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 created by security leaders with experience at companies such as CrowdStrike, Okta, Cylance, and Carbon Black. The company focuses on securing SaaS environments such as Microsoft 365 and Salesforce, helping businesses reduce risk, detect threats, and prevent breaches.

About the role

The Senior Support Engineer sits at the technical center of Obsidian’s customer support operation.

You’ll have two main responsibilities. First, you’ll take ownership of the most complex and high-severity customer issues, working through deep technical problems before they reach Engineering. Second, you’ll help build the systems that allow the support team to scale through technology, automation, and agentic AI rather than simply adding headcount.

This is a hands-on individual contributor role. The ideal person enjoys solving difficult technical problems but also looks for ways to turn those solutions into automation, playbooks, and reusable knowledge.

What you’ll do

• Own complex, high-severity, and escalated support cases from investigation through resolution.
• Act as the top technical escalation point before issues are handed to Engineering.
• Troubleshoot problems involving APIs, identity and authentication, integrations, telemetry, and product data flows.
• Work with the Head of Customer Support to build and improve agentic support systems for automated triage, resolution, and knowledge retrieval.
• Turn your troubleshooting experience into reusable automation, playbooks, and documentation that can reduce future manual work.
• Find gaps in automated and agentic support workflows and improve their accuracy and effectiveness.
• Work with Product and Engineering on root-cause analysis, bug reports, and permanent fixes.
• Help establish the technical quality standard for the support organization and mentor other support engineers.

What they’re looking for

• Strong hands-on experience in technical support or support engineering for a B2B SaaS product.
• Solid knowledge of APIs, authentication and identity, logs, telemetry, integrations, and systematic troubleshooting.
• Experience building or improving automation, agentic systems, or LLM-powered support tools—or a strong interest and ability to develop these skills.
• Ability to turn complicated, one-off customer problems into repeatable and automatable solutions.
• Comfortable working in an environment where the support function is being actively redesigned around technology.
• Cybersecurity, identity, or SaaS security experience is strongly preferred.

Nice to have

• Scripting or coding experience, particularly with Python, and confidence debugging at the API level.
• Experience with LLM or agent frameworks, retrieval-augmented generation, or workflow automation.
• Familiarity with identity provider and SaaS administration APIs, including Microsoft Graph and Microsoft Entra, or similar platforms.

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.