Technical Chief of Staff, Trail of Bits
$175-250k
+ Potential bonuses
Security engineering firm
Be an early applicant
Security engineering firm
101-200 employees
Be an early applicant
$175-250k
+ Potential bonuses
101-200 employees
Company mission
To help secure the world's most targeted organizations and products.
Role
Who you are
- 8+ years of experience, with a strong engineering or technical foundation. You have built real things and can earn instant credibility in an engineer-led culture because you are one
- A clear desire to transition from engineering into business and leadership. You are motivated by access, ownership, and understanding how a company runs, and you see this role as the path to developing a deeper understanding of how the executive level functions
- A strong bias toward action over deliberation. You move fast, prefer "good enough now" to "perfect later," and get impatient with slow processes. You are an executor
- Organized and detail-oriented with strong follow-through. You build systems so nothing falls through the cracks, even when juggling many priorities, and you are the person who circles back before anyone realizes a ball was dropped
- Strong written and verbal communication, with the judgment to handle sensitive topics and represent the CEO accurately to senior and external audiences
- 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. No task is too small, you process feedback well, and you are trustworthy with confidential information
- Fluency with AI tools and automation for operational efficiency. Familiarity with scaling frameworks like EOS (rhythm of business, accountability structures, systematic execution) is a plus
What the job involves
- The Chief of Staff drives key strategic initiatives and outcomes across Trail of Bits, serving as the CEO's right-hand person. You will act as a credible proxy for the CEO, manage his day-to-day workflow and communications, lead strategic planning, and take ownership of the follow-through that keeps the organization moving
- This role is built for an engineer who wants to move into business leadership. Trail of Bits was built by engineers for engineers, and our culture is rooted in technical excellence, intellectual rigor, and deep respect for the craft of security research and engineering. You already speak this language. What sets you apart from your peers is that you are drawn to the business: how decisions get made, how an organization scales, how a leader spends their time and attention. You would rather move an organization forward than go deeper on a single technical problem, and you are looking for a seat where you learn to operate a company from the inside
- This is a high-urgency, action-oriented role. You will be the executor in a thoughtful, deliberative organization, the person who turns intent into motion and makes sure things actually happen. You will operate with real authority as an extension of the CEO, reporting directly to him as a member of the leadership team
- Act as a credible proxy for the CEO: attend prep meetings, briefings, and stakeholder conversations on his behalf, then brief him with exactly what he needs so he shows up ready for the highest-stakes moments
- Manage the CEO's inbound communications with judgment, triaging email and Slack so that what needs a response gets one, what can be handled by you is handled, and what can be dropped is dropped, without everything routing through him
- Manage the CEO's time and attention as a precious resource, knowing what deserves his time and protecting his focus for what only he can do
- Build and maintain accountability systems that track commitments across the organization, so that when something important is asked for, it gets captured, scheduled, and completed on a predictable timeline
- Draft reports, communications, and presentations on behalf of the CEO, and prepare materials and research that make meetings productive
- Lead annual strategic planning, oversee cross-departmental projects, and coordinate key stakeholders to drive progress and decisions 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
- Propose systems to streamline the office of the CEO, coordinate new cross-functional processes, and identify the metrics that matter for tracking business and executive performance
- Reporting Manager: CEO
Our take
As more and more commercial activities go online, companies are increasingly exposed to cybersecurity threats. This requires organizations to get serious about their digital security infrastructure. As a result, the business of cybersecurity auditing has boomed.
Trail of bits is one such auditing firm with a signature method: combining its top-quality research in the cybersecurity field with the approaches of a real-world hacker. Distinguishing itself even further, the company has engaged in a new strategy fit for a new market - blockchain. The cybersecurity firm is now one of the world’s most prominent blockchain code auditors.
It's an exploding niche for which Trail of Bits has also been able to create an entirely new business line. While also auditing on behalf of blockchain software businesses, it is also expanding a service of engaging the government & large financial institutions for work on evaluating the risks of blockchain software.
Trail of Bits is well positioned as a result. Even if, as some commentators predict, the bottom falls out of the blockchain industry, the firm has used the momentum to reinforce its position as a thought leader on cutting-edge technology, establishing important partnerships that will last regardless.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
18% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Aug 2023
$4m
SEED
Jan 2018
$0.2m
GRANT
Total funding: $5.4m
Company benefits
- Health Insurance with no-monthly-premiums
- Vision, Dental, Life & Disability Insurance
- Access to Kindbody for gynecology and fertility care
- Access to HealthAdvocate, Teledoc & OneMedical
- 401k with 5% company matching
- Competitive salaries
- Ongoing bonus opportunities
- ConnectYourCare Flex Spending Account (FSA)
- Commuter Benefits
- Fitness stipends
- Four weeks of PTO
- Fifteen company holidays
- 4 months paid parental leave
- End-of-year performance bonus
- Continuing education, public presentations and blog posts
- Recruiting & referrals
- Conferences & off-sites
- Company & team outings
- Virtual events
- Continuing education
- Training sessions & learning courses
- Internal research & development Projects
- Charitable donation matching
- Relocation assistance
- 1Password subscription
- Work from home stipend
- Remote work friendly
Company HQ
Midtown East, New York, NY
Leadership
Dan Guido
(Co-Founder & CEO)Previously a Senior Security Consultant at iSEC Partners. Also worked as Threat Intelligence Lead for the U.S. Federal Reserve System. Former NSA Analyst.
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