Technical 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 will act as a credible proxy for the CEO, manage his day-to-day workflow and communications, lead strategic planning, and take ownership of the follow-through that keeps the organization moving.

This role is built for an engineer who wants to move into business leadership. Trail of Bits was built by engineers for engineers, and our culture is rooted in technical excellence, intellectual rigor, and deep respect for the craft of security research and engineering. You already speak this language. What sets you apart from your peers is that you are drawn to the business: how decisions get made, how an organization scales, how a leader spends their time and attention. You would rather move an organization forward than go deeper on a single technical problem, and you are looking for a seat where you learn to operate a company from the inside.

This is a high-urgency, action-oriented role. You will be the executor in a thoughtful, deliberative organization, the person who turns intent into motion and makes sure things actually happen. You will operate with real authority as an extension of the CEO, reporting directly to him as a member of the leadership team.

What You'll Achieve

• Act as a credible proxy for the CEO: attend prep meetings, briefings, and stakeholder conversations on his behalf, then brief him with exactly what he needs so he shows up ready for the highest-stakes moments.
• Manage the CEO's inbound communications with judgment, triaging email and Slack so that what needs a response gets one, what can be handled by you is handled, and what can be dropped is dropped, without everything routing through him.
• Manage the CEO's time and attention as a precious resource, knowing what deserves his time and protecting his focus for what only he can do.
• Build and maintain accountability systems that track commitments across the organization, so that when something important is asked for, it gets captured, scheduled, and completed on a predictable timeline.
• Draft reports, communications, and presentations on behalf of the CEO, and prepare materials and research that make meetings productive.
• Lead annual strategic planning, oversee cross-departmental projects, and coordinate key stakeholders to drive progress and decisions 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.
• Propose systems to streamline the office of the CEO, coordinate new cross-functional processes, and identify the metrics that matter for tracking business and executive performance.

What You'll Bring

• 8+ years of experience, with a strong engineering or technical foundation. You have built real things and can earn instant credibility in an engineer-led culture because you are one.
• A clear desire to transition from engineering into business and leadership. You are motivated by access, ownership, and understanding how a company runs, and you see this role as the path to developing a deeper understanding of how the executive level functions.
• A strong bias toward action over deliberation. You move fast, prefer "good enough now" to "perfect later," and get impatient with slow processes. You are an executor.
• Organized and detail-oriented with strong follow-through. You build systems so nothing falls through the cracks, even when juggling many priorities, and you are the person who circles back before anyone realizes a ball was dropped.
• Strong written and verbal communication, with the judgment to handle sensitive topics and represent the CEO accurately to senior and external audiences.
• 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. No task is too small, you process feedback well, and you are trustworthy with confidential information.
• Fluency with AI tools and automation for operational efficiency. Familiarity with scaling frameworks like EOS (rhythm of business, accountability structures, systematic execution) is a plus.

Reporting Manager: CEO

The base salary for this full-time position ranges from $175,000 to $250,000, 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 120+ 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.