Demo

Head of Operations

Trail of Bits
New York, NY Full Time
POSTED ON 2/5/2025
AVAILABLE BEFORE 8/3/2025
Who We Are

Founded in 2012 by 3 expert hackers with no investment capital, Trail of Bits is the premier place for security experts to boldly advance security and address technology's newest and most challenging risks. It has helped secure some of the world's most targeted organizations and devices. Our combination of novel research with practical solutions reduces the security risks that our clients face from emerging technologies. Our work helps drive the security industry and the public understanding of the technology underlying our world.

Cybersecurity preparedness is a moving target. Companies like ours are the tip of the spear in the fight against attackers. Our research-based and custom-engineering approach ensures that our client's capabilities are at the forefront of what's available. For companies and technologies that live and die by their security, a proactive, tailored approach is required to keep one step ahead of attackers.

Democratizing security information is essential. As part of our business, we provide ongoing informational support through blogs, whitepapers, newsletters, meetups, and open-source tools. The more the community understands security, the more they'll understand why a company like ours is so unique and valuable.

Role

Trail of Bits seeks an experienced and dynamic Head of Operations adept at balancing traditional operational excellence with a robust entrepreneurial spirit. Based in our New York City headquarters, this leader will bring strong financial acumen while overseeing our operational functions. In this vital role, you will orchestrate the annual goal-setting process, align initiatives with our strategic objectives, and drive successful execution across finance, people, IT, and program management.

Operations at Trail of Bits support four distinct consulting organizations, and we're looking for a Head of Operations who understands the unique financial dynamics of professional services firms while maintaining operational excellence at scale. We want to redefine operations within a fast-paced, innovative tech environment while fostering a supportive, inclusive, and growth-minded culture.

This unique position, ideal for a leader who thrives in dynamic environments, offers the opportunity to optimize our financial performance while scaling internal processes for growth. Your role is pivotal in building a culture where financial discipline meets operational efficiency, steering Trail of Bits towards new heights in operational excellence and commercial success.

The Head of Operations will be critical in supporting Trail of Bits' mission of being the premier place for security experts to advance security by creating an efficient business operations organization that creates efficiencies at every turn. This role will genuinely define being a multiplier in the workplace, multiplying our ability to serve our clients.

This role is hybrid but must be based in NYC.

What You'll Achieve

A successful candidate will be able to reduce the operational costs and bandwidth required by the CEO, executive team, and all client-facing stakeholders. Marrying seamless operations and expert talent will allow us to unlock revenue growth with marginal financial and operational cost increases.

  • Financial Leadership: Lead financial planning, analysis, and reporting while overseeing Finance, People, and IT. Your leadership will be instrumental in optimizing profitability, managing cash flow, and driving commercial success across all departments.
  • Tactical Performance Oversight: Develop and implement a comprehensive performance management framework that aligns with our tactical goals. This framework should track and assess performance and integrate insights across the organization to inform strategic decision-making and operational adjustments
  • Cross-functional Collaboration: Work to build and refine cross-functional processes, focusing on increasing support to our consulting arms and efficiency in decision-making. Your role will ensure that different departments work cohesively towards common organizational objectives
  • Support and Guidance: Represent and communicate strategic, operational perspectives to our leaders across the company. Your guidance will ensure that these projects and team efforts align with the company's goals and strategic direction
  • Competitive Insight: Monitor industry trends and the competitive landscape. Leverage this insight to identify and capitalize on new business opportunities, ensuring Trail of Bits remains at the forefront of the industry


What You'll Bring

  • 12 years of experience in operational leadership and program management, demonstrating your ability to navigate and succeed in a global, diverse setting
  • Based in New York City
  • Strong background in financial planning and analysis, budgeting, and strategic financial management in a professional services environment
  • Proven track record of optimizing utilization rates, project profitability, and operational efficiency in professional services firms.
  • Strong familiarity with essential tools such as GitHub, Twitter, Google Suite, and Slack, reflecting your ability to leverage technology for efficient operation and communication
  • Demonstrated ability to set, monitor, and achieve ambitious quarterly and annual goals, showcasing your results-driven approach and commitment to continuous improvement
  • Experience in dynamically building and scaling teams and systems, particularly in fast-paced and evolving environments, indicating your adaptability and growth-oriented mindset
  • Expertise in crafting and implementing effective operational strategies, demonstrating your skill in scaling business operations to meet evolving demands
  • Experience in strategic financial planning, budgeting, and analysis, demonstrating the ability to align financial resources with business and operational objectives in a professional services environment


Reporting Manager: CEO

The base salary for this full-time position ranges from $250,000 to $300,000, excluding benefits and potential bonuses. Various factors influence our salary ranges, including the specific role, level of seniority, geographic location, and the nature of the employment contract. An individual's specific work location, unique skills, experience, and relevant educational background will determine the final offer within this range. The presented salary range encompasses the starting salaries for all U.S. locations. For a precise salary estimate tailored to your preferred location, please discuss it with your recruiter during the hiring process.

Trail of Bits, Inc. participates in E-Verify, the US federal electronic employment eligibility verification program. Learn more.

Benefits

Benefits, Perks & Wellness

Trail of Bits is our people, not a place. With over 100 employees working from every time zone across the globe, our remote-first culture is built on autonomy and trust (and backed by smile-worthy benefits) for full-time employees:

Empowered Living:

  • 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


Nurturing New Beginnings:

  • 4 months of parental leave to cherish the arrival of new family members
  • Our team is global and remote-first. However, if you are interested in moving to NYC, we offer $10,000 in relocation assistance to support your transition


Work & Life Enrichment:

  • $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


Community Impact:

  • Philanthropic contribution matching up to $2,000 annually

Dedication to Diversity, Equity, Inclusion & Belonging (DEIB)

Trail of Bits is a community of innovators, risk-takers, and trailblazers who celebrate individual differences and recognize that unique perspectives make us stronger, smarter, and more successful. We actively seeks applicants who can bring a variety of experiences, perspectives, and backgrounds to the team. We provide equal employment opportunities to all employees and applicants for employment without regard to race, color, ancestry, national origin, gender, sex, pregnancy, pregnancy-related condition, sexual orientation, marital status, religion, age, disability, qualified handicap, gender identity, results of genetic testing, military status, veteran status, or any other characteristic protected by applicable law. Our team values diversity in experience and backgrounds—we do our best work when we create space for different voices and perspectives. Whatever unique experiences or skill sets you bring, we look forward to learning from each other.

Salary : $250,000 - $300,000

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