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

About the Role

At Obsidian, we relentlessly pursue clarity in a landscape defined by complexity. We’re looking for Security Research Engineers who thrive at the intersection of security research and product engineering. You’ll dig deep into SaaS platforms, craft high-impact product features, and help shape the defensive strategies that protect our customers at scale.

This role is for someone who loves gaining a deep understanding of complex systems, who enjoys thinking like an attacker, and who wants to create category-leading security solutions for Obsidian's customers.

What You’ll Do

• Gain an in-depth understanding of major SaaS or AI platforms to identify critical security insights. 
• Explore and prototype solutions to integrate data across SaaS and AI platforms to identify toxic combinations of risks that can lead to high blast-radius compromises.
• Identify and respond to new attacker techniques against SaaS and AI platforms to build novel approaches to detect or mitigate future attacks.
• Leverage AI to turbo-charge research into SaaS and AI platform security.

What We’re Looking For

Minimum Qualifications

• 5-7 years of experience in the cybersecurity industry with either a research or data focus.
• Experience with data pipelines (dbt, dagster, clickhouse).
• Proficiency in Python/Go and SQL.
• Experience with log processing and anomaly detection.
• Fluency in using AI agents to assist in building prototype solutions.
• Ability to analyze logs and signals from IdPs, cloud, or SaaS apps.

Preferred Qualifications

• Experience with core SaaS platforms such as Google Workspace, Microsoft Office 365, Salesforce, or Workday in a security context.
• Strong understanding of identity systems (Okta, Azure AD/Entra, Google Workspace, etc.) and authentication flows.

Why Join Us

• Protect some of the world's largest organizations 
• Become an expert in SaaS security by learning from the industry’s leader.
• Have a direct impact immediately, and experience Silicon Valley pace from the UK.

About the Role - as a Senior Engineer at Obsidian, you’ll:

• Build or extend data pipelines that power Obsidian’s Agentic AI and supply chain risk products.
• Maintain, improve, and evolve existing systems to ensure performance, resilience, and scalability
• Design and implement APIs and backend services, including multithreaded applications
• Collaborate with product and engineering teams to support key product themes and ensure delivery of high-impact features
• Apply strong software engineering practices to requirements gathering, system design, and code reviews
• Contribute to a fast-moving, collaborative environment where adaptability and teamwork are essential.
• Identify and proliferate best practices in data pipeline design between both the UK and US teams.

What’s in It for You

• You will have direct impact on the core product used by enterprises worldwide
• Work alongside a talented, friendly team in a supportive and collaborative culture
• Grow your skills with opportunities to learn new technologies and engineering practices
• Be part of an innovative, fast-paced environment where your contributions are valued
• Enjoy a hybrid working, with supported remote working and great office spaces in Cheltenham and Manchester

Required Skills & Experience

• 5-7 years of experience in a software engineering role
• Proficiency in one or more modern programming languages such as Python, Go, or SQL
• Experience building backend services, APIs, and multithreaded applications
• Familiarity with containerization and orchestration technologies such as Docker and Kubernetes
• Strong knowledge of relational databases (e.g., Postgres)
• Experience collaborating in team environments and adapting to changing requirements
• Understanding of software design principles and engineering best practices
• Experience with cloud platforms (AWS, GCP), object storage (S3), or event/streaming systems (Kafka, Redis)
• Familiarity with Git for version control and deployment tooling, such as GitLab CI/CD
• Experience in influencing design patterns based on best practices.
• Experience assessing alternative data architecture designs to produce accurate and unbiased recommendations.

Desirable Experience

• Experience with system monitoring and observability tools such as Grafana, Prometheus, or similar platforms
• Understanding of quality engineering (QE) practices across development and testing lifecycles
• Exposure to large-scale distributed systems and performance optimisation
• Experience in forming strong stakeholder relationships to help promote joint working between teams.
• Experience of working alongside both UK and US development teams.

AI Skills & AI-Native Engineering Expectations: As an AI-forward engineering organization, we expect senior engineers to effectively leverage AI tools and understand foundational AI concepts to enhance development efficiency and build AI-ready systems.

AI Engineering Capabilities:

• Leverage AI tools effectively to improve development efficiency and build AI-ready systems.
• Proficient with AI-powered developer tools; able to critically evaluate and refine AI-generated outputs.
• Strong understanding of core AI/ML concepts (LLMs, embeddings, vector databases, inference, evaluation).
• Experience integrating AI/ML APIs and building AI-ready data infrastructure (e.g., for RAG).
• Ensure data quality, governance, observability, reliability, security, and performance in AI-driven systems.

Team Description

The Data Engineering team is responsible for developing and maintaining the company’s data ingestion and processing pipelines. This role collaborates with data scientists, software engineers, business analysts, and technical leads to build reliable data infrastructure that supports decision-making for apparel brands and retailers. The position reports to the Technical Lead within the Data Engineering function.

Your Impact

• Contribute to the development and enhancement of data ingestion and processing pipelines
• Partner with product managers, data scientists, and engineers to build and maintain accurate and robust data infrastructure managing first- and second-party data
• Collaborate with technical leads and senior engineers on data architecture decisions and implementation strategies
• Support the team in delivering scalable solutions while learning and growing your expertise
• Work as part of a collaborative team that values creativity and continuous improvement
• Help build and maintain data pipelines that support AI and decision-making tools

Your Qualifications

• Commercial & proven experience in data engineering or related technical roles
• Proficiency in SQL and Python for data processing and pipeline development
• Experience with data warehousing concepts and ETL/ELT processes
• Hands-on experience with modern data platforms such as Snowflake, Databricks, or Redshift
• Familiarity with data orchestration tools like Apache Airflow, Prefect, or DBT
• Experience working with columnar formats like Parquet and Avro
• Understanding of data modeling, database optimization, and performance tuning
• Experience integrating data from various sources including APIs, FTP, and cloud storage

Preferred Skills

• Knowledge of streaming data processing and data APIs
• Knowledge of cloud platforms, particularly AWS
• Familiarity with infrastructure as code and CI/CD practices
• Experience with time series data

About Prophecy 

The leader in AI-native data preparation and analysis, Prophecy is revolutionizing how the world’s top enterprises turn data chaos into reliable insights. We introduce the AI-native data lifecycle (generate, refine, deploy) where our industry leading AI agents and humans work hand-in-hand in visual and document interfaces to analyze, transform and prepare data, to ship trusted insights at enterprise scale. To learn more, visit us on LinkedIn.

About the Role

As a Forward Deployed Solution Engineer, you will be a critical part of the go-to-market team owning the technical journey from initial customer engagement through to production go-live.This is a unique opportunity to operate at the intersection of engineering, sales, and customer delivery at a high-growth startup.

You are not just designing solutions you are building and shipping them. You will partner closely with Account Executives to win strategic deals, then lead hands-on implementation to ensure customers realize value quickly. This role is ideal for someone who thrives in fast-paced environments, enjoys solving ambiguous problems, and takes pride in delivering real-world impact through production systems.

What You’ll Do

• Own the Technical Win: Partner with Account Executives to lead deep technical discovery, shape solution design, and directly influence deal outcomes
• Translate Requirements into Solutions: Turn complex, ambiguous business needs into clear technical architectures, scoped plans, and executable project roadmaps
• Build & Ship Production Systems: Develop integrations, write scripts, configure APIs, and manage data flows to deliver production-ready implementations
• Drive Time-to-Value: Lead end-to-end deployments, ensuring customers reach their initial value milestones within the first 60–90 days
• Bridge Pre-Sales to Delivery: Own the transition from sales to implementation, including scoping, SOW creation, and execution
• Act as a Strategic Technical Advisor: Guide customers on architecture decisions, best practices, and long-term scalability
• Identify Expansion Opportunities: Partner with customers to uncover additional use cases and drive continued adoption and growth
• Close the Product Feedback Loop: Surface recurring challenges and contribute to product improvements through technical insights and specifications
• Operate with Ownership: Manage multiple high-impact projects simultaneously, maintaining a high bar for quality and execution

What You’ll Need

• 5+ years of experience in technical pre-sales (Solutions Engineering, Sales Engineering)
• 5+ years in a customer-facing role (Forward Deployed Engineering, Implementation Engineering, or Software Engineering)
• Strong hands-on experience building and shipping production systems in customer environments
• Proficiency in SQL and at least one scripting language (Python, JavaScript, or similar)
• Experience working with APIs, webhooks, and system integrations
• Familiarity with modern data stacks (e.g., Snowflake, Databricks, BigQuery) and ETL workflows
• Experience in cloud environments (AWS, Azure, or GCP)
• Ability to translate complex technical concepts into clear business outcomes for both technical and non-technical stakeholders

Preferred Qualifications

• Experience in a high-growth startup or fast-paced environment
• Background in solution architecture or technical pre-sales
• Experience authoring Statements of Work (SOWs) and scoping customer implementations
• Familiarity with data modeling, data pipelines, and large-scale data systems
• Comfort working across the full customer lifecycle, from pre-sales through post-deployment

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