About this role.
Obsidian Security is seeking a Senior Support Engineer to resolve complex, high-severity SaaS security support escalations and serve as the final technical escalation point before Engineering. The role requires deep troubleshooting across APIs, authentication and identity, integrations, telemetry, and product data flows. A major component is designing and improving agentic, LLM-enabled support automation, converting successful resolutions into reusable playbooks and automated workflows. The engineer will collaborate closely with Support leadership, Product, and Engineering while mentoring peers and raising the technical quality bar. This is a senior individual-contributor role in a rapidly evolving support organization with substantial ownership and ambiguity.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
Skills and capabilities most closely associated with this opportunity.
Sample interview questions
I would first establish impact, severity, scope, and a reproducible timeline. I would use logs, API traces, configuration details, and controlled testing to isolate the failure domain, maintain clear customer updates, and engage Engineering with concise evidence when a product defect is suspected. After resolution, I would document the root cause and create a playbook or automation opportunity to prevent recurrence.
I would validate the integration configuration, permissions, token lifecycle, scopes, tenant settings, and relevant identity-provider audit logs. I would compare expected and observed API responses, identify whether the issue is authorization, authentication, network, data-ingestion, or product-processing related, and test the smallest safe correction. I would then clearly explain both the immediate remediation and preventative configuration guidance to the customer.
I identify repeated decision patterns in ticket investigations, standardize the required inputs and validation steps, and build a reliable workflow around them. For example, an automation can collect diagnostic context, validate common configuration errors, retrieve approved knowledge, and either provide a safe resolution or route the case with complete evidence. I measure outcomes such as deflection, resolution accuracy, escalation rate, and customer satisfaction before expanding use.
I would use curated, version-controlled knowledge sources; constrain the agent to approved actions; and require confidence thresholds and human escalation for high-risk or uncertain cases. Sensitive customer data should be minimized, access-controlled, and logged appropriately, while responses should cite supporting evidence where possible. I would continuously test for hallucinations, unsafe recommendations, data exposure, and poor routing behavior using representative support scenarios.
I would provide a concise escalation package containing business impact, severity, reproduction steps, timestamps, logs, API evidence, expected versus actual behavior, and any workarounds already attempted. I would remain accountable for customer communication while partnering on prioritization and validation of the fix. Once resolved, I would update internal documentation and review whether monitoring, product changes, or automation can detect the issue earlier.
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 New Zealand, 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—Microsoft 365, 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.
Senior Support Engineer
Team: Global Services & Delivery Location: [Remote / Hybrid – specify] Reports to: Head of Customer Support
About the role
Obsidian Security protects organizations against threats across their SaaS and identity environments. This role sits at the technical center of how we deliver support. It has two mandates. First, you own our hardest problems: complex, high-severity, and escalated tickets that require deep technical diagnosis. Second, you help build the systems that will let us scale support through technology rather than headcount, partnering directly with the Head of Customer Support to design and operationalize our agentic support capability.
This is a hands-on individual contributor role for someone who is equally comfortable resolving the toughest customer issue in the queue and turning that resolution into automation that prevents the next one.
What you’ll do
- Own complex, high-severity, and escalated tickets end to end, acting as the top technical escalation point before engineering.
- Diagnose deep technical issues across APIs, identity and authentication, integrations, telemetry, and product data flows.
- Partner with the Head of Customer Support to design, build, and continuously tune agentic support systems, including automated triage, resolution, and knowledge retrieval.
- Convert your own resolution work into reusable automation, playbooks, and knowledge that agentic systems can execute without human involvement.
- Identify where automation and agentic resolution fail, then close those gaps to raise deflection and automated resolution quality.
- Interface with Product and Engineering on root cause analysis, bug escalation, and permanent product fixes.
- Set the technical quality bar for the support function and mentor other engineers on it.
What we’re looking for
- A strong hands-on technical support or support engineering background for a technical B2B SaaS product. Cybersecurity, identity, or SaaS security context is strongly preferred.
- Depth across APIs, authentication and identity, logs and telemetry, integrations, and systematic debugging.
- Demonstrated experience building or tuning automation or agentic and LLM-based support tooling, or clear aptitude and appetite for doing so.
- The ability to translate messy, one-off escalations into repeatable, automatable solutions.
- Comfort operating with ambiguity in a function that is being actively rebuilt around technology.
Nice to have
- Scripting or coding ability, for example Python, and comfort debugging at the API level.
- Experience with LLM and agent frameworks, retrieval-augmented generation, or workflow automation.
- Familiarity with identity provider and SaaS administrative APIs, such as Microsoft Graph and Entra, or comparable platforms relevant to SaaS security.
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.
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 accommodations@obsidiansecurity.com
Information collected and processed as part of any job applications you choose to submit is subject to Obsidian’s Applicant Privacy Policy.
Base Salary Range
$100,000—$130,000 USD
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