Chief of Staff

About the Role

You will act as the CEO's right-hand partner, managing their day-to-day workflow and serving as a thought partner on company strategy. You will build and maintain accountability systems, conduct after-action reviews of critical incidents, draft reports and presentations, prepare the CEO for key meetings, and lead annual strategic planning. You will own difficult performance conversations, coordinate cross-departmental projects, design process improvements and training, and define metrics to track business performance.

Requirements

  • 8+ years in consulting, program management, or operational roles in tech companies
  • Experience supporting executives and helping teams hit ambitious goals
  • Exceptional writing and presentation skills for senior and board audiences
  • Comfortable working with engineering teams and technical decision-making
  • Strong project management, organization, and attention to detail
  • Ability to operate as an extension of the CEO with real authority
  • High ownership mentality and trustworthiness with confidential information
  • Familiarity with EOS or similar scaling frameworks; experience with AI tools for operational efficiency is a plus

Responsibilities

  • Manage the CEO's day-to-day workflow
  • Act as a thought partner on company strategy
  • Build and maintain accountability systems
  • Conduct after-action reviews and propose process improvements
  • Draft reports, speeches, and presentations for the CEO
  • Prepare the CEO for meetings with research and materials
  • Lead annual strategic planning and oversee cross-departmental projects
  • Own difficult performance and expectation conversations
  • Coordinate training sessions and propose systems to streamline operations
  • Identify and track key business performance metrics

Benefits

  • Performance-based bonuses
  • Company-paid health, dental, vision, disability, and life insurance
  • 401(k) with 5% match
  • 20 days paid vacation
  • 4 months parental leave
  • $10,000 relocation assistance to New York City
  • $1,000 working-from-home stipend
  • $750 annual learning and development stipend
  • Company-sponsored all-team celebrations with travel and accommodation
  • Philanthropic contribution matching up to $2,000 annually

Skills

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Chief of Staff at Trailofbits. | JobStash