Chief of Staff

About

Trail of Bits is a company that specializes in software security and assurance. Established in 2012, it has assisted some of the most targeted organizations worldwide in securing their systems.

Trail of Bits combines advanced security research with a practical attacker mindset to reduce risk and strengthen software code. The company offers services in software assurance, security engineering, and research and development, focusing on areas such as blockchain, cryptography, and mobile device security.

They also provide expert training courses to enhance understanding of various security aspects like penetration testing and threat modeling.

Description

• 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

• 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

• 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.