Chief of Staff

2 days ago

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Trail of Bits

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Cybersecurity • SaaS • Blockchain

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.

51 - 200 employees

Founded 2012

🔒 Cybersecurity

☁️ SaaS

📋 Description

• Manage the CEO's day-to-day workflow and act as a thought partner on company strategy, ensuring focus on the right priorities to achieve organizational goals. • Build and maintain accountability systems that track commitments across the organization so that when the CEO asks for something important, it gets captured, scheduled, and completed on a predictable timeline. • Conduct after-action reviews following critical incidents (customer escalations, PR issues, operational failures), gathering context from multiple sources and proposing documented process improvements. • Draft reports, speeches, and presentations on behalf of the CEO; prepare the CEO for meetings by researching and creating materials that facilitate productive engagement. • Lead annual strategic planning, oversee cross-departmental projects, and coordinate key stakeholders to drive progress and decision-making on the company's most complex challenges. • Take ownership of difficult conversations about performance and expectations, communicating firmly and clearly across the organization while building trust and maintaining collaborative relationships. • Coordinate training sessions on new processes, propose systems to streamline operations, and identify metrics that matter for tracking business performance.

🎯 Requirements

• 8+ years in consulting, program management, or operational roles in tech companies, with a track record of helping executives and teams hit ambitious goals. • Exceptional at writing and presenting to senior audiences, with experience giving board-level presentations and drafting communications that are clear, accurate, and appropriate for sensitive topics. • Comfortable working with engineering teams and technical decision-making; you can learn what makes technical work valuable and earn credibility in an engineer-led culture. • Organized and detail-oriented with strong project management skills; you build systems to make sure nothing falls through the cracks, even when juggling multiple priorities. • Able to operate as an extension of the CEO with real authority; when you tell someone something needs to happen, they know it carries the same weight as hearing it directly from the CEO. • Low ego and high ownership mentality; no task is too small, you process feedback well, and you're trustworthy with confidential information. • Familiarity with scaling frameworks like EOS (rhythm of business, accountability structures, systematic execution) is a major plus; experience with AI tools and automation for operational efficiency is also valuable.

🏖️ 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 interested in 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.