VP of Operations

Remote /
Operations – Operations /
About Trail of Bits
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.

Reporting to the CEO, this role will lead the operational function of the company. The VP of operations will be responsible for the annual goal-setting process, aligning initiatives to those goals, and driving the successful execution of cross-functional programs. The focus of this role stretches across the organization and will oversee the breadth of program planning and management in the areas of IT, Finance, and Legal. 

Trail of Bits is looking for a highly motivated, analytical, objective, and operational manager to mature and improve our internal processes. The VP of operations is a newly created leadership role and will bring together operations excellence, change management, and business operations. We are looking for a strong leader to ensure effective scale and growth for Trail of Bits.


    • Lead the operations of the IT, Finance, and Legal teams. 
    • Create, implement and manage a strategic plan for the operations team.
    • Identify procedural gaps in existing workflows and work to resolve them with optimization, automation, and data.
    • Mature our business operations function to maximize the impact to our business and ensure we are building processes that allow us to scale and can be successfully measured.
    • Build and optimize cross-functional processes and practices to drive increased transparency and quick action.
    • Outline a process to produce, review and aggregate performance metrics for Trail of Bits operations.
    • Partner closely with leadership to evolve our company OKR goals process.
    • Translate practical needs into technical and/or business requirements.
    • Work closely with People Operations to create, implement and refine company policies and procedures.
    • Guide and support the work of leadership team members and cross-functional projects.
    • Support and collaborate on the creation of internal and external materials. 
    • Monitor the competitive landscape recommend business opportunities based on trends.


    • 10 - 15 years of managerial experience demonstrating a strong ability in operational leadership and program management in a global capacity.
    • Demonstrated experience building and leading a high-performance, globally distributed cybersecurity team.
    • GitHub, Twitter, Google Suite, Slack, and Culture Amp experience required.
    • Demonstrated experience setting, monitoring and meeting quarterly and annual goals.
    • Experience building and scaling teams and systems.
    • Expertise in defining and crafting operational strategy and scaling business operations.
    • Proven strategic planning and budgeting experience.
    • Excellent interpersonal, public speaking and problem-solving skills

Company Perks

    • Before, during and after COVID-19, our workforce works flexibly. Many employees choose to work from home around the globe. As long as 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 professional growth with working at Trail of Bits.
    • We routinely highlight the amazing work our employees do via our blog, product offerings, and conference talks. We celebrate you!
    • We're at the forefront of a number of 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 Eligible 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: $5k one-time
    • Charitable donation matching up to $2,000
    • 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

Benefits for Eligible 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 & inclusion
Trail 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.