Security Audits 101: Insights & Best Practices from Trail of Bits
Vanessa Gennarelli
Cybersecurity isn't just a checkbox—it's a journey. In a recent session hosted by Vanessa, COO and co-founder at Workbrew, experts from the elite security firm Trail of Bits shared deep insights into how organizations can approach, structure, and benefit from security audits. The conversation was packed with practical advice and real-world examples.
Meet the Experts
- Lindsay Rakowski – Sales Manager at Trail of Bits, with a background in education, passionate about helping organizations understand cybersecurity.
- Chris Dahlheimer – Leader of the Sales Engineering team at Trail of Bits, former Department of Defense specialist, focused on proactive network defense and threat intelligence.
Why Security Audits Matter
Security audits go beyond bug hunting. They're about improving the overall architecture, design, infrastructure, and security posture of a system. Firms like Trail of Bits help organizations:
- Identify weaknesses early
- Strengthen system architecture
- Guide long-term security strategies
Their holistic approach integrates security into every phase of the development lifecycle.
Types of Security Assessments
Trail of Bits offers a range of services, each tailored to where a company is in its security journey:
- Design Reviews – Ensure architectural soundness before coding begins
- Threat Modeling – Identify and prioritize potential threats
- Infrastructure & Cloud Security Reviews – Analyze configuration and environment risks
- Integrated Security Reviews – Combine static and dynamic analysis
- Rapid Risk Assessments – Conduct early for a quick look into your security posture or post-incident evaluations to prevent recurrence
- Code Reviews – In-depth assessments of mature codebases
When to Start: Timing Is Everything
Start early. Stay continuous.
Waiting until the end of a product cycle can be costly. Instead:
- Start with a design review
- Follow with threat modeling
- Conduct infrastructure reviews
- Wrap with code reviews before launch
Engaging security partners early builds institutional knowledge, reduces rework, and maximizes effectiveness.
How to Prepare for a Security Audit
Maximize the value of your audit with smart preparation:
- Set clear goals
- Fix low-hanging bugs before the audit
- Provide comprehensive documentation
- Include unit and integration tests
- Share previous reports and known issues
Well-prepared teams get more impactful, strategic insights from their audits.
Choosing the Right Security Partner
When selecting a vendor:
- Check credentials and reputation
- Review past public reports
- Look for research contributions and open-source work
- Evaluate communication and collaboration style
- Ensure actionable, long-term recommendations
Trail of Bits emphasizes transparency, deep expertise, and a consultative approach.
Turning Audit Results Into a Competitive Advantage
Audit results aren't just for internal use—they can be a strategic asset:
- Demonstrate maturity to customers, partners, and investors
- Improve product stability and development processes
- Signal security leadership in your industry
- Prioritize future investments based on real data
Publishing updated audit results after remediation builds trust and confidence.
In-House vs. Third-Party: The Right Balance
Trail of Bits recommends a hybrid approach:
- Build internal security teams for day-to-day needs
- Use third-party experts for niche or advanced issues
External partners bring a fresh, unbiased perspective and help level up your internal capabilities over time.
Final Takeaway
Security isn’t a one-time task—it’s a continuous, strategic process. Engaging with experienced firms like Trail of Bits early and often ensures you’re building secure, resilient, and trusted systems from the ground up.
Start early. Stay secure. Think long-term.
Interested in a security audit or just want to learn more? Visit Trail of Bits or reach out to their team to start the conversation.
Check out Workbrew's Trust Center to access our report from Trail of Bits, or try Workbrew for free.