IT Operations Engineer

Trail of Bits

11d•Remote

About The Position

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.

Requirements

Significant experience in IT Operations, DevOps, or Systems Administration -- we care more about what you can demonstrate than how many years you've been doing it
Strong background in endpoint management using MDM systems or open-source tools
Previous experience as the primary or solo IT person at a company
Experience inheriting and improving existing infrastructure -- not just greenfield builds
Strong programming skills in Python and Bash
Comfortable writing production-quality scripts and tools that scale, not just code that works
Experience automating workflows and building internal tooling
Able to review others' code and provide constructive, technically grounded feedback
Expert-level macOS administration experience with deep familiarity with MDM, system configuration, and endpoint management
Experience managing Windows and Linux devices
Experience with authentication and access control protocols including OAuth 2.0, SAML, FIDO/U2F, TOTP/HOTP, and other multi-factor authentication methods
Experience with Google Workspace administration, 1Password or similar credential management, and identity providers (Entra or similar)
Experience managing cloud infrastructure on AWS, Azure, or GCP
Demonstrated ability to audit, rationalize, and optimize cloud environments -- not just provision new resources
SOC 2 compliance knowledge required
Experience responding to client security questionnaires and providing compliance documentation
Familiarity with NIST SP 800-171, NIST SP 800-53, CMMC, or FedRAMP is a plus
Experience with vulnerability scanning and patch management processes
Familiarity with zero-trust security architectures is a plus
Excellent written communication skills -- you'll write documentation, runbooks, and security policies that others rely on
Strong organizational skills and ability to manage multiple priorities independently
Comfortable providing support and guidance to a remote, technical workforce
Systems thinker: you diagnose root causes, not just symptoms, and build processes that prevent recurrence

Nice To Haves

Background working at a cybersecurity or security-focused organization
Experience with infrastructure-as-code
Experience inheriting and stabilizing IT environments during periods of organizational growth or transition

Responsibilities

Test, deploy, and maintain MDM solutions (Jamf Pro) and endpoint security tools (CrowdStrike Falcon, iVerify)
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
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
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
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
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.
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.
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