Chief of Staff

Trail of Bits

9h•$175,000 - $250,000•Remote

About The Position

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.

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.

Nice To Haves

Familiarity with scaling frameworks like EOS (rhythm of business, accountability structures, systematic execution) is a plus.

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.

Benefits

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.
4 months of parental leave to cherish the arrival of new family members.
$10,000 in relocation assistance to support your transition to NYC.
$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.
Philanthropic contribution matching up to $2,000 annually.