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

• 8+ years in consulting, program management, or operational roles in tech companies, with a track record of helping executives and teams hit ambitious goals.
• Exceptional at writing and presenting to senior audiences, with experience giving board-level presentations and drafting communications that are clear, accurate, and appropriate for sensitive topics.
• Comfortable working with engineering teams and technical decision-making; you can learn what makes technical work valuable and earn credibility in an engineer-led culture.
• Organized and detail-oriented with strong project management skills; you build systems to make sure nothing falls through the cracks, even when juggling multiple priorities.
• Able to operate as an extension of the CEO with real authority; when you tell someone something needs to happen, they know it carries the same weight as hearing it directly from the CEO.
• Low ego and high ownership mentality; no task is too small, you process feedback well, and you're trustworthy with confidential information.
• Familiarity with scaling frameworks like EOS (rhythm of business, accountability structures, systematic execution) is a major plus; experience with AI tools and automation for operational efficiency is also valuable.

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:

• 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.

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.