AI Systems Engineer

Founded in 2012 by 3 expert hackers with no investment capital, Trail of Bits is the premier place for security experts to boldly advance security and address technology’s newest and most challenging risks. It has helped secure some of the world's most targeted organizations and devices. Our combination of novel research with practical solutions reduces the security risks that our clients face from emerging technologies. Our work helps drive the security industry and the public understanding of the technology underlying our world.

Cybersecurity preparedness is a moving target. Companies like ours are the tip of the spear in the fight against attackers. Our research-based and custom-engineering approach ensures that our client’s capabilities are at the forefront of what’s available. For companies and technologies that live and die by their security, a proactive, tailored approach is required to keep one step ahead of attackers.

Democratizing security information is essential. As part of our business, we provide ongoing informational support through blogs, whitepapers, newsletters, meetups, and open-source tools. The more the community understands security, the more they’ll understand why a company like ours is so unique and valuable.

Are you a builder who sees opportunities to automate, streamline, and enhance how teams work? As our AI Systems Engineer, you will work directly with our CEO at our NY office to design and ship internal tools that transform how Trail of Bits operates. In this high-impact role, you will identify friction points across the organization and build practical solutions that leverage AI, automation, and modern development practices.

You will own projects from conception to deployment, working in our Slack-first culture where ideas move fast and impact is measured by what you ship. Your work will become part of the operational infrastructure that powers a world-class security consulting firm.

This is a full-time role based in our NYC office with remote flexibility.

• Build and deploy internal tools that solve real operational challenges across engineering, operations, and go-to-market teams.
• Design AI-powered workflows that enhance team productivity, knowledge management, and decision-making.
• Create automation systems that eliminate manual processes and unlock team efficiency.
• Integrate AI capabilities (like Claude) into existing workflows and communication platforms like Slack.
• Collaborate directly with the CEO and senior leadership to identify high-impact opportunities and iterate rapidly on solutions.
• Ship production-ready code that becomes part of Trail of Bits' operational infrastructure.

• Recently completed a degree in Computer Science, Engineering, or a related technical field.
• Strong software development skills with a track record of shipping projects—whether personal, academic, or professional.
• Proficiency in modern programming languages (Python, JavaScript/TypeScript, or similar) and enthusiasm for learning new technologies quickly.
• Experience or strong interest in AI integration, API development, and workflow automation.
• Builder mindset: you see a problem and your instinct is to code a solution.
• Comfort working in fast-paced, loosely-structured environments where you define your own projects.
• Excellent communication skills—you can translate technical work into business impact.
• Bonus: Experience with Slack apps, AI APIs (OpenAI, Anthropic), web scraping, data processing, or cybersecurity tools.
• Extra bonus: Experience with Capture the Flag (CTF) challenges or other engineering/development competitions.

Reporting Manager: Dan Guido, CEO 

The base salary for this full-time position ranges from $125,000 to $250,000, excluding benefits and potential bonuses. Various factors influence our salary ranges, including the specific role, level of seniority, geographic location, and the nature of the employment contract. An individual's specific work location, unique skills, experience, and relevant educational background will determine the final offer within this range. The presented salary range encompasses the starting salaries for all U.S. locations. For a precise salary estimate tailored to your preferred location, please discuss it with your recruiter during the hiring process.

Trail of Bits, Inc. participates in E-Verify, the US federal electronic employment eligibility verification program. Learn more.

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Trail of Bits is our people, not a place. With over 100+ employees working from every time zone across the globe, our remote-first culture is built on autonomy and trust (and backed by smile-worthy benefits) for full-time employees:

Empowered Living:

• Competitive salary complemented by performance-based bonuses.
• Fully company-paid insurance packages, including health, dental, vision, disability, and life.
• A solid 401(k) plan with a 5% match of your base salary.
• 20 days of paid vacation with flexibility for more, adhering to jurisdictional regulations.

Nurturing New Beginnings:

• 4 months of parental leave to cherish the arrival of new family members.
• Our team is global and remote-first. However, if you are interested in moving to NYC, we offer $10,000 in relocation assistance to support your transition.

Work & Life Enrichment:

• $1,000 Working-from-Home stipend to create a comfortable and productive home office.
• Annual $750 Learning & Development stipend for continuous personal and professional growth.
• Company-sponsored all-team celebrations, including travel and accommodation, to foster community and recognize achievements.

Community Impact:

• Philanthropic contribution matching up to $2,000 annually.