Chief of Staff

3 days, 3 hours ago
Full-time
Lead
Operations
Trail of Bits

Trail of Bits

Trail of Bits is a leading company specializing in computer and network security. Since 2012, they have been helping secure the world's most targeted organizations and products by combining high-end security research with a real-world attacker mentalit...

Internet Software & Services
51-250
Founded 2012

Description

  • Act as a credible proxy for the CEO in prep meetings, briefings, and stakeholder conversations.
  • Manage the CEO’s inbound communications across email and Slack by triaging, responding, or routing as appropriate.
  • Protect and prioritize the CEO’s time and attention on the highest-value activities.
  • Build and maintain accountability systems that track commitments and ensure follow-through across the organization.
  • Draft reports, communications, presentations, and briefing materials on behalf of the CEO.
  • Lead annual strategic planning and coordinate cross-departmental projects and stakeholders.
  • Drive progress and decisions on the company’s most complex challenges.
  • Handle difficult performance and expectation conversations clearly while maintaining trust and collaboration.
  • Propose systems and metrics to streamline the office of the CEO and improve executive operations.

Requirements

  • 8+ years of experience with a strong engineering or technical foundation.
  • Demonstrated desire to transition from engineering into business and leadership.
  • Strong bias toward action and comfort moving quickly with practical, timely decisions.
  • Excellent organization, detail orientation, and follow-through across many priorities.
  • Strong written and verbal communication skills for sensitive topics and senior or external audiences.
  • Ability to operate as an extension of the CEO with real authority.
  • Low ego, high ownership, and strong trustworthiness with confidential information.
  • Fluency with AI tools and automation for operational efficiency.
  • Familiarity with scaling frameworks like EOS is a plus.

Benefits

  • Base salary of $175,000 to $250,000, excluding benefits and potential bonuses.
  • Performance-based bonuses.
  • Fully company-paid health, dental, vision, disability, and life insurance.
  • 401(k) plan with a 5% company match.
  • 20 days of paid vacation with flexibility for more, subject to local regulations.
  • 4 months of parental leave.
  • $10,000 relocation assistance for candidates moving to NYC.
  • $1,000 work-from-home stipend and a $750 annual learning and development stipend.
  • Company-sponsored all-team celebrations with travel and accommodation covered.
  • Philanthropic contribution matching up to $2,000 annually.

Interested in this position?

Apply directly on the company website

Apply Now

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