Technical Chief of Staff
About the 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.
Responsibilities
- 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
Requirements
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
Qualifications
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.