Trail of Bits

Trail of Bits secures some of the world's most targeted organizations—from tech giants like Facebook to government agencies like DARPA. Since 2012, this cybersecurity research and consulting firm has specialized in reverse engineering, cryptography, and software security audits. Their team of around 100 security engineers doesn't just find vulnerabilities—they build custom tools, develop security features, and train engineering teams to write safer code. Recent wins include second place in DARPA's AI Cyber Challenge ($3M prize) and recognition as a leader in The Forrester Wave for cybersecurity consulting.

Remote-first since founding, the team spans 30+ countries across every time zone. Work is asynchronous by design: engineers collaborate through Slack, Google Docs, and GitHub rather than constant meetings. The culture emphasizes cross-team learning—security engineers regularly join projects outside their specialty to pick up new skills. With four weeks of PTO, 15 company holidays, and twice-yearly offsites, the company balances deep technical work with connection time. Engineers own projects end-to-end and contribute to Trail of Bits' extensive open-source security tooling, from static analyzers to fuzzing frameworks.

Trail of Bits offers comprehensive benefits including health insurance with no monthly premiums, 5% 401k match, four months paid parental leave, and annual learning stipends. Engineers receive work-from-home stipends, fitness allowances, and bonuses for continuing education, conference speaking, and internal research. The company maintains flexible hours to accommodate the distributed team and provides relocation assistance for those who prefer proximity to the NYC headquarters.