Chief of Staff, Assurance

Trail of Bits


About Trail of BitsTrail 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.RoleWorking closely with the assurance practice director, the chief of staff, assurance practice will serve as a key problem-solver for the assurance practice. They will support the assurance practice director in the organization, management and execution of projects. The chief of staff, assurance practice will be responsible for ensuring key initiatives are delivered in a timely fashion with a high level of accuracy. The mission of this role is to be project focused and operate effectively so that initiatives are all broken into timelines, milestones, and deliverables. This is a critical role on the team; to drive the success of the assurance team’s operations. The chief of staff, assurance practice needs to be technically minded to understand the specifics of each project; e.g., the assignment, feedback from our SMEs (project managers, technical editors, finance, people operations etc.) and accurate project implementation. The assurance practice chief of staff also needs to be strategically minded to fit each project  into the big picture of the organization’s growth plan. 


    • Responsible for the day to day workflow of all assurance practice operations. 
    • Oversee cross-departmental projects and initiatives by bringing together key stakeholders to drive process, progress, and decision-making. 
    • Be a strategic planning partner to the assurance practice director when supporting the strategy and goals of the practice. 
    • Assist the assurance practice director in strategically aligning projects with key priorities, milestones, deadlines, and decisions to maximize execution.
    • Drive best practices, communication, and coordination between the assurance practice director and other key leaders to enable effective collaboration across the organization.
    • Propose the creation of new systems and processes to streamline operations.
    • Identify and track key performance indicators for the practice.
    • Manage internal and external team communications, projects and priorities.
    • Engage and manage applicable external relationships; research and identify potential new partners, maintain ongoing communication and arrange meetings to support ongoing relationship building. 


    • At least 8 years of experience in technical consulting and/or an operational role within the cybersecurity industry.
    • Strong technical background with degree in computer science or related field, or equivalent industry experience:
    • Deep familiarity with CI/CD pipelines and Agile methodologies.
    • Deep familiarity with modern software development frameworks and languages; cloud-native development.
    • Solid foundation in information security, verification driven testing, code audits.
    • Experience with operation and management of blockchain technologies, application security.
    • Understanding of cryptographic principles and implementations.
    • Demonstrated excellence in consulting and consulting management. 
    • Demonstrated excellence guiding high-performing executives/teams of executives in working together to achieve company and team goals.
    • Exceptional organization skills and work ethic with impeccable attention to detail.
    • Strong influencing skills as well as ability to communicate directly to drive accountability where required.
    • Experience and comfort interacting across all levels of an organization, from management and partners to entry-level professionals.
    • Well-honed project management skills with the ability to manage multiple disparate projects.
    • Systems thinking and the ability to imagine and drive the creation of new structures or processes required for business success.
    • Agility to multitask and prioritize in a rapidly changing environment in the face of many competing priorities.

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.
    • 3-4 months paid parental leave.
    • 401k with 5% company matching through Betterment.
    • Moving expenses: $5,000k 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.

Benefits for Canadian Employees

    • Premium health, vision, and dental insurance plans.
    • Life/AD&D Insurance options, as well as short- and long-term disability insurance plans.
    • RRSP plan with 5% company matching.
    • Charitable donation matching up to USD $2000.
    • 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.
    • 10 days of Paid Time Off (PTO) and 10 days of sick time per year.
    • 14 company holidays including provincial statutory holidays and select US holidays per year.
    • Carbon offsets for your personal and corporate carbon emissions through Project Wren.

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.