Principal Security Engineer, Trail of Bits
Application Security
$200-235k
+ Performance-based bonuses
TypeScript
JavaScript
Python
Java
Go
Kotlin
Swift
C++
C
Rust
Objective-C
Senior and Expert level
Remote from US
Security engineering firm
Be an early applicant
Security engineering firm
21-100 employees
B2BEnterpriseSaaSCyber Security
Be an early applicant
$200-235k
+ Performance-based bonuses
TypeScript
JavaScript
Python
Java
Go
Kotlin
Swift
C++
C
Rust
Objective-C
Senior and Expert level
Remote from US
21-100 employees
B2BEnterpriseSaaSCyber Security
Company mission
To help secure the world's most targeted organizations and products.
Role
Who you are
- Deep Application Security Expertise: 8+ years of experience in application security with demonstrated mastery across web, mobile, cloud, and system-level security domains, including extensive experience identifying and mitigating sophisticated vulnerabilities in enterprise and security-critical software
- AI Security Assessment: Demonstrated interest and experience in leveraging AI for security workflows, whether through custom tooling, LLM-assisted code review, or automated vulnerability detection, with an understanding of both the opportunities and limitations of AI in security
- Leadership Experience: Proven track record of leading complex security engagements, mentoring engineers, and driving projects to successful completion while maintaining deep technical involvement and high-quality deliverables
- Advanced Assessment Capabilities: Extensive experience conducting comprehensive security assessments, including penetration testing, code review, architecture analysis, and threat modeling across diverse technology ecosystems with a track record of discovering critical vulnerabilities
- Low-Level Security Proficiency: Strong foundation in system internals, memory corruption vulnerabilities, binary analysis, and reverse engineering with the ability to move fluidly between application-layer and system-level security concerns
- Multi-Language Code Review Mastery: Expert-level proficiency in manual code review across JavaScript/TypeScript, Python, Go, and additional languages such as Rust, C/C++, Java/Kotlin, Swift/Objective-C, with deep understanding of language-specific security pitfalls and secure coding patterns
- SAST/DAST Expertise: Hands-on experience with static and dynamic analysis tools, including customization, rule development, and integration into security assessment workflows, with ability to evaluate tool effectiveness and build custom solutions where needed
- Threat Modeling Excellence: Proven ability to lead sophisticated threat modeling exercises for complex systems, applying frameworks like STRIDE, PASTA, or custom approaches while facilitating productive sessions with diverse stakeholder groups
- Consulting Excellence: Strong client-facing skills with ability to communicate complex technical findings to both technical and executive audiences, build lasting client relationships, and translate security research into business value
What the job involves
- Trail of Bits seeks a Principal Security Engineer, Application Security to lead our Software Assurance practice's most complex and high-impact client engagements
- As a technical leader, you will drive comprehensive security assessments, mentor team members, and shape the strategic direction of application security initiatives while maintaining deep hands-on involvement in critical security work
- You will serve as the technical authority on engagements involving sophisticated software systems, leading threat modeling exercises, conducting architecture reviews of complex distributed systems, and performing deep code analysis across modern and legacy codebases
- Your expertise will span from high-level application security consulting to low-level vulnerability research, with the ability to navigate both domains seamlessly
- Beyond individual contributions, you'll provide technical leadership across the Application Security team, developing methodologies, building tooling that scales our impact, and representing Trail of Bits at the forefront of application security innovation
- You'll work directly with C-level executives and engineering leaders at our most strategic clients, translating complex security findings into business impact and actionable roadmaps
- In addition to leading private sector engagements, you will have opportunities to collaborate with our Research & Engineering team to secure funding from government agencies for advanced security research, contribute to publications, and advance the state of the art in application security
- AI Security Innovation: Apply and advance the use of AI in application security workflows, from leveraging LLMs for code analysis and vulnerability pattern recognition to assessing the security of AI-powered applications and ML systems themselves
- Advanced Security Assessment: Conduct and oversee comprehensive security assessments across diverse technology stacks, including modern web applications, cloud-native architectures, mobile platforms, and system-level software, identifying critical vulnerabilities in authentication systems, API security, access controls, and platform security mechanisms
- Threat Modeling & Architecture Review: Lead sophisticated threat modeling exercises and architecture security reviews for complex distributed systems, cloud environments, and emerging technology platforms, working directly with client architects and engineering leadership to identify systemic security weaknesses and design secure solutions
- Code Review Excellence: Perform expert-level manual code reviews across multiple languages (JavaScript/TypeScript, Python, Go, Rust, C/C++, and others), identifying subtle security flaws, logic vulnerabilities, and implementation weaknesses that automated tools miss, while developing custom static analysis rules and detection techniques
- Security Tooling & Automation: Design and build advanced security tools and frameworks that leverage SAST/DAST capabilities, integrate AI/ML for vulnerability detection and code analysis, and scale the team's assessment capabilities while pushing the boundaries of automated security testing
- Technical Leadership: Lead complex, high-stakes application security engagements from scoping through delivery, providing technical direction to multidisciplinary teams and ensuring exceptional quality of security assessments and recommendations
- Strategic Consulting: Serve as a trusted security advisor to client leadership, providing strategic guidance on security program maturity, secure development lifecycle integration, and long-term security roadmap development while delivering findings that drive meaningful organizational change
- Team Development: Mentor senior and staff engineers, conduct technical training, develop assessment methodologies, and contribute to the growth and technical excellence of the Application Security practice
- Thought Leadership: Represent Trail of Bits through conference presentations, blog posts, open-source contributions, and research publications that advance the application security field and strengthen our industry presence
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
Gowanus, 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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