Trail of Bits logo
Trail of Bits

Deepening the Science of Security

Technical Chief of Staff

Chief of StaffChief of StaffFull TimeRemoteLeadTeam 51-200Since 2012H1B No SponsorCompany SiteLinkedIn

Location

New York

Posted

9 days ago

Salary

$175K - $250K / year

Seniority

Lead

Bachelor Degree8 yrs expEnglish

Job Description

Technical Chief of Staff

Trail of Bits

• Act as a credible proxy for the CEO: attend prep meetings, briefings, and stakeholder conversations. • Manage the CEO's inbound communications with judgment. • 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.

Job 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 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.

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Technical Chief of Staff

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