• Support the data engineering team in managing workflow orchestration tools (e.g., Apache Airflow or AWS Step Functions) for production-grade data pipelines. • Design, build, and maintain robust CI/CD pipelines (utilizing GitLab) to ensure seamless, automated software delivery and data pipeline deployments. • Design and deploy scalable, secure, cloud infrastructure leveraging Infrastructure as Code (IaC) best practices to support high-availability healthcare applications. • Implement comprehensive monitoring, logging, and alerting systems to ensure platform reliability and performance, providing visibility into both application health and data processing speeds. • Act as a primary defender of our environment; ensure all infrastructure remains compliant with strict healthcare data regulations, specifically HIPAA and HITRUST. • Work closely with software and data engineers to optimize system architecture and performance of databases (PostgreSQL, Snowflake) and workflow orchestration tools (e.g., Apache Airflow or AWS Step Functions). • Evaluate and implement emerging tools and technologies that improve the developer experience and system resilience.

Trail of Bits is a cybersecurity firm of ~100 people across 14+ countries, fully remote since our founding in 2012. We conduct security audits, build research tools, and set standards the industry adopts. Our clients include the largest tech companies, financial institutions, and government agencies. The Role Trail of Bits seeks an IT Operations Engineer to own and evolve our internal IT infrastructure, security compliance, and employee technology experience. Here's what makes this different from IT at most companies: our workforce is security researchers and engineers. They audit the cryptographic protocols that protect financial infrastructure, build open-source security tools used across the industry, and assess the security of systems trusted by millions of users. They have strong, specific opinions about how corporate IT should be configured -- and they're usually right. Your job is to listen to that expertise, implement it reliably, and build the automation and tooling that keeps our systems in a state that matches the standards we set for our clients. You'll take technical direction from people who deeply understand the threat landscape, and you'll exercise your own initiative to build, improve, and automate everything you touch. Our IT infrastructure has scaled with the company over 14 years, and like any growing organization, it needs someone who can assess what's in place, strengthen the foundations, and build from there. Your first priority will be understanding the environment end-to-end -- auditing what's deployed against what's documented, establishing operational discipline across our toolchain, and closing gaps. Once the foundation is solid, you'll build the automation and self-service tooling that takes our operations to the next level. This is a builder role with high accountability. You'll write production-quality code -- not just scripts that work, but tools that scale. You'll automate repetitive tasks, build self-service tooling, and promote consistent, seamless experiences for a fully remote and globally distributed team. You'll also be responsible for endpoint management, SaaS administration, security compliance, and cloud infrastructure. The ideal candidate possesses a "no task too small, no task too big" attitude, proactively owns and solves problems, and thrives working autonomously as the primary IT person for a deeply technical team. You should be comfortable balancing initiative -- you see the gap and close it -- with the discipline to take direction, document transparently, and never cut corners on process. This role is open to candidates authorized to work in the United States. What You'll Achieve Endpoint Device Management - Test, deploy, and maintain MDM solutions (Jamf Pro) and endpoint security tools (CrowdStrike Falcon, iVerify) - Our fleet is primarily macOS (~100 devices), with additional Windows and Linux endpoints driven by the diversity of our client and research work. Expert-level macOS management is the foundation; candidates with multi-OS experience will thrive given the breadth of our engagements. - Maintain strict parity between the configuration repository and what is deployed across the fleet. The repo is the source of truth -- drift between documented and deployed state is unacceptable. - Manage Apple Business Manager, device lifecycle (ordering, provisioning, recovery), and automated onboarding/offboarding workflows - Enforce macOS update policies and patch management across the fleet Identity & Access Management - Manage identity and access across the SaaS ecosystem including Google Workspace (with Context-Aware Access), 1Password, Microsoft Entra, GitHub, Slack, and other platforms - Set up and integrate new systems with SSO (SAML, OIDC, OAuth 2.0) - Enforce account lifecycle hygiene: provisioning on day one, prompt suspension on departure, regular audits of authorized devices and access - Maintain organizational systems for credential management -- vaults, naming conventions, cross-references Security & Compliance - Maintain SOC 2 compliance posture and manage compliance automation platforms (Vanta) - Respond to client security questionnaires and provide compliance documentation for engagements across government, defense, and enterprise sectors - Manage endpoint detection and response (CrowdStrike Falcon), network canaries (Thinkst), email security (Material Security), and mobile device verification (iVerify) - Proactively maintain security posture through vulnerability scanning, configuration audits, and patch management - Monitor for and respond to supply chain threats -- package manager attacks, extension supply chain risks, dependency vulnerabilities -- with real-time detection where possible - Write and maintain security policies, runbooks, and documentation Cloud Infrastructure - Manage and rationalize cloud infrastructure across GCP and other providers -- understand what's running, why, what it costs, and whether it should still exist - Maintain accurate inventory, eliminate waste, and enforce least-privilege access for service accounts and cloud IAM - Develop reporting to monitor fleet health, compliance state, and infrastructure costs Automation & Tooling - Automate repetitive tasks across the company through scripting and custom tooling - Build internal tools to improve employee self-service - Maintain and extend workflow automation and internal tooling infrastructure - Manage developer tooling governance: Claude API access, VS Code extension security, GitHub organization administration and Advanced Security - Evaluate and implement new technologies to improve operational efficiency -- with rigorous vetting. In an era of AI-generated and AI-adjacent tooling, we hold ourselves to a higher standard for what enters our environment. Every tool, integration, and dependency must be evaluated for security posture before adoption. Documentation & Transparency - Document every configuration, script, and policy change in GitHub and public Slack channels. Anyone in the organization should be able to understand what is running on their machine at any given time. - Work visibly. Planned changes announced in advance, coverage gaps flagged early, status always obvious. Leadership should never have to ask what's happening in IT. - Maintain the IT scripts and configuration repository as the single source of truth for what is deployed across the fleet. Technical Support & Availability - Provide technical support and guidance to employees in a remote-first environment via Slack - Provide coverage for critical issues outside standard business hours -- password resets, account lockouts, and urgent security events cannot always wait for Monday - Review code contributions to IT repositories and provide meaningful technical feedback - Identify security events and integrate alerting processes into Slack Why This Role Matters At most companies, IT security is a checkbox exercise. At Trail of Bits, our internal security posture is an extension of our reputation. Our employees audit critical infrastructure for the world's most targeted organizations -- they notice when their own company's systems fall short. Nation-state adversaries have real reasons to target a firm like ours. The IT Operations Engineer is the person who ensures that our internal systems are as resilient as the standards we set for our clients. When you do this well, 100 people across 14 countries work without friction, leadership never has to intervene in IT, and our own house is in order -- visibly, provably, and at all times.

• Design, implement, and manage GCP-based infrastructure ensuring scalability, performance, and cost efficiency. • Build and maintain CI/CD pipelines that support reliable deployments and automated testing. • Implement Infrastructure as Code (IaC) and automate environment setup and configuration. • Establish and maintain observability frameworks : monitoring, logging, and alerting for uptime and performance. • Collaborate with Security and Engineering to enforce least privilege, compliance, and Zero Trust principles. • Troubleshoot and optimize system performance, ensuring high availability and disaster recovery readiness. • Contribute to DevOps best practices and mentor other engineers on automation, cloud, and reliability.

• Design, build, and maintain CI/CD pipelines across development, QA, training, and production environments • Standardize and optimize deployment processes for consistent, reliable, and scalable delivery • Administer and support Azure DevOps pipelines, including repositories, agent pools, environments, and service connections • Implement infrastructure-as-code (IaC) and reusable automation solutions for environment setup and application delivery • Configure and support cloud and on-premises environments to ensure performance, stability, and alignment with business needs • Drive adoption of automated testing, validation checks, and quality gates within CI/CD pipelines • Troubleshoot build, deployment, and environment issues and perform root cause analysis • Implement monitoring, alerting, and logging solutions to improve reliability and reduce risk • Leverage AI-assisted tools to enhance development workflows, code validation, and pipeline efficiency • Evaluate and recommend tools and process improvements to increase delivery performance and developer productivity • Partner with engineering teams throughout planning, design, and delivery processes • Provide guidance on DevOps best practices, deployment strategies, and pipeline design • Act as a liaison across development, infrastructure, security, networking, and data teams • Ensure delivery processes meet security and compliance standards, including access controls and audit requirements • Maintain documentation for systems, pipelines, and processes and identify improvement opportunities