Staff Site Reliability Engineer

Staff Site Reliability Engineer

As a Staff SRE at Obsidian, you will define and drive the company-wide reliability vision for a complex, multi-tenant SaaS platform serving enterprise and financial customers. You will operate as a strategic partner to DevOps and Platform Engineering leadership, shaping a unified reliability strategy that scales across the organization.

Your core mandate: ensure Obsidian detects, diagnoses, and communicates system issues before customers are impacted—consistently and predictably.

This is a hands-on technical role that involves architecting and leading the implementation of systems that handle real-world complexity, including upstream SaaS dependencies, sparse and noisy signals, and mission-critical enterprise workloads.

Key Responsibilities

• Reliability Strategy & Architecture - Define and lead long-term reliability strategy across services. Establish end-to-end system visibility frameworks and guide architecture for observability, detection, and resilience.


• Cross-Org Leadership - Partner across teams to embed reliability, standardize SLI/SLOs, and serve as a technical escalation expert.


• Detection & Observability - Build intelligent detection systems (anomaly detection, connector health models) and enable self-service observability.


• Incident Management - Define and evolve a tiered incident communication strategy, improve response practices, and lead postmortems to strengthen reliability and customer trust.


• Execution - Contribute hands-on to system design, monitoring, and debugging across distributed systems and data pipelines.

Required Qualifications

• 5+ years in SRE, Production Engineering, or related roles


• 3+ years operating at a senior or technical leadership level (Staff or equivalent scope)


• Deep expertise in:




• AWS and/or GCP


• Kubernetes and Helm


• Observability stacks (Prometheus, Grafana, or equivalent)


• CI/CD systems (GitLab CI/CD, ArgoCD, etc.)




• Proven experience designing and scaling reliability systems for multi-tenant SaaS platforms


• Strong debugging and systems thinking across distributed microservices and legacy systems


• Demonstrated ability to lead initiatives that improve incident detection, response, and system resilience


• Hands-on engineering approach with a track record of building—not just configuring—reliability systems

Preferred Qualifications

• Experience in B2B SaaS serving enterprise or financial customers


• Familiarity with third-party SaaS connector architectures and ingestion patterns


• Experience building anomaly detection or intelligent alerting systems


• Experience designing customer-facing status pages and incident communication frameworks

Why This Role

• Drive org-wide reliability strategy


• Own and build new detection & observability systems


• Tackle complex distributed systems challenges


• Safeguard critical infrastructure for financial customers

What Success Looks Like

• Issues caught and resolved before customer impact


• Reliability is measurable and continuously improving


• Teams self-serve observability with scalable tools


• Clear, proactive incident communication builds trust


• Reliability becomes a competitive advantage