Engineering – AI Systems Engineer

Job Description: • 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. Requirements: • 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. 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 to NYC. • $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. • Philanthropic contribution matching up to $2,000 annually. Apply tot his job Apply To this Job