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Freelance Offensive Security Engineer Jobs in Reston, VA

TwinThread

Offensive Security Engineer

Mclean, VA · On-site

$120 - $160/hr

We are seeking candidates with a passion for offensive security, deep technical expertise in ... Experience in reverse engineering thick‑client and mobile applications to identify ...

Humana

Senior Engineer, Offensive Security

Washington, DC

$129K - $177K/yr

As Senior Offensive Security Engineer, AI-Driven Red Team & Tooling, you'll build the AI and agentic tooling that makes our offensive operations faster and broader, then prove it where it counts, on ...

Humana

Senior Engineer, Offensive Security

Washington, DC

$129K - $177K/yr

As Senior Offensive Security Engineer, AI-Driven Red Team & Tooling, you'll build the AI and agentic tooling that makes our offensive operations faster and broader, then prove it where it counts, on ...

Humana

Senior Engineer, Offensive Security

Washington, DC

$129K - $177K/yr

As Senior Offensive Security Engineer, AI-Driven Red Team & Tooling, you'll build the AI and agentic tooling that makes our offensive operations faster and broader, then prove it where it counts, on ...

Humana

Lead, Offensive Security

Washington, DC · Remote

This requires a production software engineering mindset, not proof-of-concept scripting. Your first ... Offensive Security identifies weaknesses so the business can fix them before adversaries exploit ...

Humana

Lead, Offensive Security

Washington, DC · Remote

This requires a production software engineering mindset, not proof-of-concept scripting. Your first ... Offensive Security identifies weaknesses so the business can fix them before adversaries exploit ...

Humana

Lead, Offensive Security

Washington, DC · Remote

This requires a production software engineering mindset, not proof-of-concept scripting. Your first ... Offensive Security identifies weaknesses so the business can fix them before adversaries exploit ...

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All JobsOffensive Security Engineer JobsFreelance Offensive Security Engineer JobsFreelance Offensive Security Engineer Jobs in Reston, VA

Freelance Offensive Security Engineer information

See Reston, VA salary details

$15

$49

$137

How much do freelance offensive security engineer jobs pay per hour?

As of Aug 18, 2026, the average hourly pay for freelance offensive security engineer in Reston, VA is $49.63, according to ZipRecruiter salary data. Most workers in this role earn between $25.24 and $64.28 per hour, depending on experience, location, and employer.

What is a freelance offensive security engineer?

Freelance Offensive Security Engineers are independent cybersecurity professionals who specialize in identifying and exploiting vulnerabilities within computer systems, networks, and applications. They are hired by organizations on a contract basis to conduct penetration testing, red teaming, and security assessments to help improve the organization's defenses. Unlike in-house employees, freelancers work for multiple clients and often bring a diverse range of experience from different industries. Their primary goal is to simulate real-world attacks and provide detailed reports with recommendations to enhance security posture.

What are the key skills and qualifications needed to thrive as a freelance offensive security engineer?

To thrive as a Freelance Offensive Security Engineer, you need deep expertise in penetration testing, vulnerability assessment, and cybersecurity best practices, often backed by certifications like OSCP or CEH. Familiarity with tools such as Metasploit, Burp Suite, Nmap, and scripting languages like Python is typically required. Strong problem-solving skills, self-motivation, and effective client communication set standout professionals apart in this field. These competencies are crucial for identifying and mitigating security risks while maintaining client trust and delivering high-value security assessments.

What are some common challenges faced by freelance offensive security engineers when working with multiple clients?

Freelance Offensive Security Engineers often juggle multiple projects for different clients, which can make time management and prioritization challenging. Each client may have unique security requirements, varying network environments, and distinct expectations for deliverables. Additionally, staying updated on the latest vulnerabilities and attack techniques is crucial, as clients rely on your expertise for thorough assessments. Clear communication and diligent documentation are essential to ensure that findings and recommendations are understood and actionable for each client.

What is the difference between Freelance Offensive Security Engineer vs Penetration Tester?

AspectFreelance Offensive Security EngineerPenetration Tester
CertificationsOSCP, CEH, OSWEOSCP, CEH, GPEN
Work EnvironmentProject-based, remote or on-site, client-specificTypically consulting, testing environments, often on-site or remote
Employer/Industry UsageFreelance, cybersecurity firms, consultingSecurity firms, internal security teams, consulting

Freelance Offensive Security Engineers and Penetration Testers both focus on identifying security vulnerabilities. However, Freelance Offensive Security Engineers often work on broader offensive security projects, including red teaming and security architecture, while Penetration Testers primarily conduct targeted vulnerability assessments. The roles overlap but differ in scope and depth of engagement.

What are popular job titles related to Freelance Offensive Security Engineer jobs in Reston, VA?

For Freelance Offensive Security Engineer jobs in Reston, VA, the most frequently searched job titles are:

What job categories do people searching Freelance Offensive Security Engineer jobs in Reston, VA look for?

The top searched job categories for Freelance Offensive Security Engineer jobs in Reston, VA are:

What cities near Reston, VA are hiring for Freelance Offensive Security Engineer jobs?

Cities near Reston, VA with the most Freelance Offensive Security Engineer job openings:

Freelance Offensive Security Engineer jobs near you
Infographic showing various Freelance Offensive Security Engineer job openings in Reston, VA as of August 2026, with employment types broken down into 100% Full Time. Highlights an 67% In-person, 7% Hybrid, and 26% Remote job distribution, with an average salary of $103,235 per year, or $49.6 per hour.

Offensive Security Engineer, Agent Products

OpenAI

Washington, DC • On-site

Full-time

Re-posted 19 days ago

Job description

Job Summary:
OpenAI is an AI research and deployment company dedicated to ensuring that general-purpose artificial intelligence benefits all of humanity. They are seeking a Principal-level Offensive Security Engineer to conduct deep penetration testing of their agent-powered products and infrastructure, identify vulnerabilities, and collaborate with engineering teams to implement security improvements.
Responsibilities:
• Conduct deep penetration tests of OpenAI’s agent-powered products, including web applications, APIs, cloud services, identity and authorization flows, CI/CD systems, and model-integrated product surfaces.
• Continuously hunt for exploitable vulnerabilities in the interactions between the applications, infrastructure, tools, and models that power our agentic products.
• Perform code review, architecture review, and hands-on exploitation to validate risk and identify subtle or novel failure modes.
• Produce clear, actionable findings with reproduction steps, exploitability analysis, impact assessment, and practical remediation guidance.
• Partner directly with engineering teams to drive fixes, validate remediation, and improve secure design patterns across agentic products.
• Build tools, test harnesses, and automation to scale penetration testing across rapidly evolving product surfaces.
• Leverage advanced automation and OpenAI technologies to optimize your offensive security work.
• Share attacker-informed insights with security and engineering teams to improve threat models, mitigations, and defensive coverage.
Qualifications:
Required:
• 7+ years of hands-on penetration testing, product security assessment, application security, cloud security assessment, or equivalent offensive security experience.
• Deep expertise finding, exploiting, documenting, and helping remediate vulnerabilities in complex production systems.
• Experience performing offensive security assessments of modern technology products, including web applications, APIs, cloud infrastructure, identity systems, CI/CD pipelines, and distributed services.
• Experience designing, developing, or assessing the security of AI-powered systems.
• Experience finding, exploiting, and mitigating common vulnerabilities in AI systems, including prompt injection, confused deputies, unsafe tool use, and dynamically generated UI components.
• Exceptional skill in code review to identify novel and subtle vulnerabilities.
• Proven experience performing offensive security assessments in at least one hyperscaler cloud environment. Azure experience is preferred.
• Demonstrated mastery assessing complex technology stacks, including: Highly customized Kubernetes clusters, Container environments, CI/CD pipelines, GitHub security, macOS and Linux operating systems, Data science tooling and environments, Python-based web services, React-based frontend applications.
• Strong intuitive understanding of trust boundaries and risk assessment in dynamic contexts.
• Excellent coding skills, capable of writing robust tools and automation for offensive security testing.
• Ability to communicate complex technical concepts effectively through clear reports, practical remediation guidance, and compelling technical storytelling.
• Proven track record of not just finding vulnerabilities, but actively contributing to solutions in complex codebases.
Preferred:
• Background or expertise in AI or data science.
• Prior experience working in tech startups or fast-paced technology environments.
• Experience in related disciplines such as Software Engineering, Product Security, Application Security, Detection Engineering, Site Reliability Engineering, Security Engineering, or IT Infrastructure.
Company:
OpenAI is an AI research and deployment company that develops advanced AI models, including ChatGPT. It is a sub-organization of OpenAI Foundation. Founded in 2015, the company is headquartered in San Francisco, USA, with a team of 1001-5000 employees. The company is currently Late Stage.

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