Technical Chief of Staff

1 month, 1 week ago
Full-time
Lead
Project and Program Management
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 meetings, briefings, and stakeholder conversations.
  • Manage the CEO’s inbound communications across email and Slack, triaging and responding as appropriate.
  • Protect and prioritize the CEO’s time and attention for the highest-value decisions and activities.
  • Build and maintain accountability systems to track commitments, deadlines, and follow-through across the organization.
  • Draft reports, communications, presentations, and meeting materials on behalf of the CEO.
  • Lead annual strategic planning and coordinate cross-departmental projects and key stakeholders.
  • Own difficult conversations about performance and expectations while maintaining trust and collaboration.
  • Propose systems and cross-functional processes that improve the office of the CEO and business execution.
  • Identify and track the metrics needed to monitor executive and business performance.

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 making progress quickly without over-deliberating.
  • Highly organized and detail-oriented with strong follow-through.
  • Strong written and verbal communication skills, including judgment for sensitive topics and senior/external audiences.
  • Ability to operate as an extension of the CEO with real authority.
  • Low ego, high ownership, and comfort handling confidential information.
  • Fluency with AI tools and automation for operational efficiency.
  • Familiarity with scaling frameworks like EOS is a plus.
  • Experience building real things and earning credibility in an engineer-led culture.

Benefits

  • Base salary of $175,000 to $250,000, excluding benefits and potential bonuses.
  • Competitive salary with 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 where permitted.
  • 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.

Interested in this position?

Apply directly on the company website

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