Okay, I've searched for Web Application Penetration Tester roles with technical lead duties in McLean, VA or remote, requiring 8+ years of experience and certifications such as OSWE or Burp Suite Certified Practitioner. I have found 42 positions for you.

Sure. Here's the analysis:

Job Analysis:

This role as Web Application Penetration Tester – Technical Lead at Freddie Mac is fundamentally designed to strengthen the organization's cybersecurity posture by rigorously testing its defenses through simulated attacks focused on web applications but also spanning infrastructure, cloud environments, and social engineering. The core purpose is to identify and exploit vulnerabilities before malicious actors can, then translate highly technical findings into actionable remediation and risk insights for diverse stakeholders. This means the candidate must combine deep technical proficiency in penetration testing tools, scripting, and vulnerability analysis with excellent communication and leadership skills to mentor others and influence security improvements. The role’s emphasis on collaboration across teams and the integration of web application security into broader threat emulation scenarios implies frequent cross-functional coordination and strategic thinking. A successful candidate will be autonomous yet collegial, bringing innovative approaches to tools and methodologies while navigating complex, evolving security landscapes. They will face challenges like balancing thorough testing with operational constraints, adapting to fast-changing tech environments, and guiding remediation processes that require both technical acumen and consensus-building. Performance will likely be measured by the quality and impact of findings, engagement leadership, and contributions to team capability development within security policy and process frameworks.

Company Analysis:

Freddie Mac is a pivotal player in the U.S. housing finance market, operating at the intersection of financial services and public mission. As a market leader with deep ties to national housing stability, it functions with a strong emphasis on risk management, regulatory compliance, and mission-driven impact—"Making Home Possible" is not just a slogan but a core guiding principle. This makes the security role especially critical, as safeguarding Freddie Mac’s systems is essential to preserving market stability and consumer trust. The company culture likely values precision, responsibility, and continuous improvement within a structured but innovation-friendly environment. Candidates in this role can expect to work in a mission-oriented organization where collaboration across business units and technology teams is vital. The position sits on an internal Red Team with visibility to leadership through engagement ownership and subject matter expertise, positioning the technical lead as a crucial contributor to strategic security objectives. Given Freddie Mac’s stable but evolving nature, this role serves both to maintain rigorous security standards and to drive modernization through innovation—balancing legacy systems with cloud-native and DevSecOps advancements. The candidate must navigate this environment with both technical mastery and an understanding of the company’s broader social and regulatory responsibilities.

Absolutely. Here are some mock interview questions that could come up:

• Behavioral: Tell me about a time when you identified a critical vulnerability in a web application. How did you communicate the risk to technical and non-technical stakeholders, and what was the outcome?
• Behavioral: Describe an instance where you had to mentor a junior team member through a complex penetration test. How did you balance guidance with autonomy?
• Behavioral: Give an example of when you challenged the status quo in a security process or methodology. What motivated you and what was the impact?
• Behavioral: How have you managed competing priorities between thorough security testing and business operational constraints?
• Technical: Walk me through your approach to performing a comprehensive web application penetration test, from scoping through remediation.
• Technical: How do you stay current with emerging vulnerabilities and public disclosures relevant to web application security? Can you share a recent example?
• Technical: What techniques do you use to bypass Web Application Firewalls (WAFs), and how do you document and validate these during testing?
• Technical: Describe your experience with scripting or programming languages like Python or JavaScript in automating penetration testing tasks or building tools.
• Situational: Imagine you find a critical vulnerability but the responsible development team is resistant to immediate remediation. How would you handle this situation?
• Situational: The scope of a Red Team engagement expands mid-assessment to include cloud-native environments you have limited experience with. How do you proceed?
• Situational: A less experienced team member makes a significant error during an assessment that impacts timelines. How do you address this while maintaining team morale?
• Company Fit: Why do you want to work at Freddie Mac, and how do you see your role contributing to the mission of Making Home Possible?
• Company Fit: Freddie Mac operates in a highly regulated environment. How do you integrate compliance considerations into your penetration testing and security recommendations?
• Company Fit: Our culture emphasizes collaboration across teams and continuous innovation. How do you foster both in your current work?
• Questions for Interviewer: How does Freddie Mac’s Red Team integrate its findings with broader organizational risk management and security operations?
• Questions for Interviewer: What are the biggest security challenges Freddie Mac anticipates over the next 12 months, and how would this role contribute to addressing them?
• Questions for Interviewer: Can you describe the growth opportunities and professional development support available for the Technical Lead within the Red Team?