Chief of Staff

at Trail of Bits

294 d. ago
About the Job

Trail of Bits helps secure the world’s most targeted organizations and products. We combine high-end security research with a real-world attacker mentality to reduce risk and fortify code.As a cybersecurity research and consulting firm, we serve clients in the defense, tech, finance, and blockchain industries. We help with their most difficult security challenges by designing and building new technology, researching new techniques to advance the state of practice, and reviewing the security of the latest available technology products before they hit the market.Our team consumes, produces, and presents research as a natural part of doing business. When we make new discoveries or developments, we strive to share our knowledge and release our tools as open-source. It’s a practice that’s earned us industry accolades and helped contribute to our double-digit bottom-line growth.Trail of Bits is seeking a Chief of Staff. The Chief of Staff is a key role on the leadership team. This individual will report to the CEO, interface with the executive team, support strategic initiatives, and drive accountability for goals across the company. The ideal candidate is a proven leader with a blend of strategic, operational, project management, and leadership skills. Additionally, they should possess exceptional attention to detail, initiative, and critical thinking skills. They are curious, adaptable, and comfortable managing change and ambiguity. They enjoy solving complex problems, are highly collaborative, and have a strong bias toward action and results. They exercise exceptional discretion with confidential information.Responsibilities for this role focus on: 1) Executive Team Leadership and Company Strategy, 2) Operations, and 3) Communications.


    • Assist the CEO in day-to-day operational management of the business and ensure the CEO’s priorities are effectively executed.
    • Own prioritization and execution of key company strategic initiatives by partnering with the executive team and internal functions.
    • Enhance the effectiveness of key meetings by setting effective agendas and driving high-quality content and output, including preparation and meeting follow-ups.
    • Support the development of and drive scorecard success metrics and KPIs. Monitor key metrics and flag areas of concern.
    • Own and continuously improve company operating cadence (e.g., executive team meetings, leadership offsites, quarterly OKRs reviews, quarterly board meetings).
    • Seek areas for improvement and innovation to make the overall business run more smoothly and drive growth.
    • Assist with communications between and from leadership to the broader team.
    • Lead the preparation and development of all executive presentations, including but not limited to reviews, all-hands meetings, internal and external speaking engagements, offsites, and events.


    • 8+ years of management consulting experience
    • Proven experience at a fast, high growth startup in a Chief of Staff or business operations leadership
    • Experience building software or managing a software developer team
    • Exposure to Cybersecurity-relevant work
    • 5+ years of project and change management expertise
    • Demonstrate analytical and logic skills with a focus problem solving frameworks
    • Excellent communication skills, both verbal and written
    • Excellent GSuite skills

Company Perks

    • Before, during, and after COVID-19, our workforce works flexibly. Many employees choose to work from home around the globe. If you deliver against your goals, we encourage you to harness your personal working style to let you work best.
    • Liberal expense policy for acquiring the equipment and software that help you do your job. If we need hardware to work effectively, we buy it. 
    • We offer exceptional and tailored technical, leadership, and organizational training for our team members. Everyone is encouraged to identify additional opportunities for personal and professional growth with working at Trail of Bits.
    • We routinely highlight our employees' fantastic work via our blog, product offerings, and conference talks. We celebrate you!
    • We're at the forefront of several markets and have the internal expertise and the ambition to capitalize on those opportunities. Our employees see their work in use and valued by many others.

Benefits for US Employees

    • Multiple generous health, vision, and dental insurance plans including no-monthly-premium options supporting individuals and families through JustWorks.
    • Ancillary benefits including life and disability insurance, pre-tax commuter benefits, free Citi Bike membership, access to a HealthAdvocate, a healthcare Flexible Spending Account (FSA), and a free One Medical membership.
    • 4 months paid parental leave.
    • 401k with 5% company matching through Betterment.
    • Moving expenses: $5,000 one-time.
    • Charitable donations matching up to $2,000.
    • One time $1,000 at home office expense stipend.
    • $500/year personal learning & development budget. 
    • Executive coaching for managers and above.
    • Options for coworking space (some restrictions may apply). 
    • Bonuses for recruiting, public speaking, tool releases, blog posts, academic posters, proposals, and whitepapers, and end-of-year bonuses based on company, team, and personal performance.
    • 20 days of Paid Time Off (PTO) per year.
    • 14 company holidays per year.
    • Carbon offsets for your personal and corporate carbon emissions through Project Wren.
    • Manage your student loans right alongside your 401(k) in Betterment.
Dedication to diversity, equity & inclusionTrail of Bits is committed to creating and maintaining a diverse and inclusive workplace where our employees can thrive and be themselves! We welcome all persons into our community. We embrace the diversity of gender, gender identity or expression, race, color, religious creed, national origin, ancestry, age, physical and mental disabilities, medical condition, genetic characteristic, sexual orientation, marital status, family care or medical leave status, military or veteran status, or perceived membership in any of these groups.