AI Systems Engineer

Trail of Bits is a premier security consulting firm founded in 2012 by expert hackers. As an AI Systems Engineer, you will work directly with the CEO to design and implement internal tools that enhance operational efficiency and leverage AI capabilities across the organization. Responsibilities 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 Skills 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 Experience with Slack apps, AI APIs (OpenAI, Anthropic), web scraping, data processing, or cybersecurity tools Benefits 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. 4 months of parental leave to cherish the arrival of new family members. $10,000 in relocation assistance to support your transition. $1,000 Working-from-Home stipend to create a comfortable and productive home office. $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. Philanthropic contribution matching up to $2,000 annually. Company Overview Since 2012, Trail of Bits has helped secure some of the world’s most targeted organizations and products. It was founded in 2012, and is headquartered in New York, New York, USA, with a workforce of 51-200 employees. Its website is