Chief of Staff

Trail of Bits

Chief of Staff driving strategic initiatives at Trail of Bits, managing CEO's workflow and strategic planning. Act as a credible proxy for CEO with authority in daily operations.

Posted 6/4/2026full-timeRemote • 🇺🇸 United StatesLead💰 $175,000 - $250,000 per yearWebsite

About the role

Key responsibilities & impact

Act as a credible proxy for the CEO: attend prep meetings, briefings, and stakeholder conversations on his behalf.
Manage the CEO's inbound communications with judgment, triaging email and Slack.
Manage the CEO's time and attention as a precious resource.
Build and maintain accountability systems that track commitments across the organization.
Draft reports, communications, and presentations on behalf of the CEO.
Lead annual strategic planning and oversee cross-departmental projects.
Take ownership of difficult conversations about performance and expectations.
Propose systems to streamline the office of the CEO and identify critical metrics for business performance.

Requirements

What you’ll need

8+ years of experience, with a strong engineering or technical foundation.
A clear desire to transition from engineering into business and leadership.
A strong bias toward action over deliberation.
Organized and detail-oriented with strong follow-through.
Strong written and verbal communication, with the judgment to handle sensitive topics.
Able to operate as an extension of the CEO with real authority.
Low ego and high ownership.
Fluency with AI tools and automation for operational efficiency.

Benefits

Comp & perks

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 if moving 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.

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

engineeringtechnical foundationoperational efficiencymetrics identificationstrategic planningproject oversight

Soft Skills

communicationjudgmentorganizationdetail-orientedfollow-throughownershipbias toward actionability to handle sensitive topics