Security Audits 101: Insights & Best Practices from Trail of Bits

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.