Chief of Staff

Who We Are

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.

Role

The Chief of Staff drives key strategic initiatives and outcomes across Trail of Bits, serving as the CEO's right-hand person. You'll manage the CEO's day-to-day workflow, lead strategic planning, coordinate after-action reviews on critical incidents, and take ownership of the difficult conversations that keep the organization accountable.

Trail of Bits was built by engineers for engineers. Our culture is rooted in technical excellence, intellectual rigor, and deep respect for the craft of security research and engineering. You'll work alongside highly technical founders and team members who value substance, precision, and authentic understanding. You must be comfortable in this environment, bringing strategic and operational expertise while genuinely investing in learning what makes our technical work unique and valuable.

The Chief of Staff is a member of the leadership team, reporting directly to the CEO, and operates with real authority as an extension of the CEO.

What You'll Achieve

• Manage the CEO's day-to-day workflow and act as a thought partner on company strategy, ensuring focus on the right priorities to achieve organizational goals.
• Build and maintain accountability systems that track commitments across the organization so that when the CEO asks for something important, it gets captured, scheduled, and completed on a predictable timeline.
• Conduct after-action reviews following critical incidents (customer escalations, PR issues, operational failures), gathering context from multiple sources and proposing documented process improvements
• Draft reports, speeches, and presentations on behalf of the CEO; prepare the CEO for meetings by researching and creating materials that facilitate productive engagement.
• Lead annual strategic planning, oversee cross-departmental projects, and coordinate key stakeholders to drive progress and decision-making on the company's most complex challenges.
• Take ownership of difficult conversations about performance and expectations, communicating firmly and clearly across the organization while building trust and maintaining collaborative relationships.
• Coordinate training sessions on new processes, propose systems to streamline operations, and identify metrics that matter for tracking business performance.

What You'll Bring

Reporting Manager : CEO

The base salary for this full-time position ranges from $175,000 to $300,000, 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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Benefits

Benefits, Perks & Wellness

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 :

Nurturing New Beginnings :

Work & Life Enrichment :

Community Impact :

Dedication to Diversity, Equity, Inclusion & Belonging (DEIB)

Trail of Bits is a community of innovators, risk-takers, and trailblazers who celebrate individual differences and recognize that unique perspectives make us stronger, smarter, and more successful. We actively seeks applicants who can bring a variety of experiences, perspectives, and backgrounds to the team. We provide equal employment opportunities to all employees and applicants for employment without regard to race, color, ancestry, national origin, gender, sex, pregnancy, pregnancy-related condition, sexual orientation, marital status, religion, age, disability, qualified handicap, gender identity, results of genetic testing, military status, veteran status, or any other characteristic protected by applicable law. Our team values diversity in experience and backgrounds—we do our best work when we create space for different voices and perspectives. Whatever unique experiences or skill sets you bring, we look forward to learning from each other.