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Weekend Offensive Security Engineer Jobs (NOW HIRING)

SPAN

Sr. Offensive Security Engineer

San Francisco, CA · On-site

$138K - $184K/yr

Designing a flexible and distributed electrical grid The Role We are looking for a hands-on individual with an offensive security engineering mindset to join us as a Senior Offensive Security ...

webAI

Senior Offensive Security Engineer (AppSec)

Austin, TX · On-site

$113K - $155K/yr

They are seeking a highly technical, hands-on Cybersecurity Engineer who combines an offensive security mindset with deep expertise in secure software development to secure their Rust-based software ...

Thrive

Security Engineer, Offensive Security

Tampa, FL · On-site

They are seeking a Security Engineer to join their Offensive Security team, responsible for advanced vulnerability management and penetration testing services while ensuring client satisfaction and ...

Praetorian

Offensive Security Manager

The Mission Praetorian is an expert-driven offensive security company. Our mission is to prevent ... You're in the work - raising the bar on delivery, developing the engineers around you, and holding ...

Humana

Senior Engineer, Offensive Security

Louisville, KY · On-site

$110K - $150K/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

New York, NY · On-site

$125K - $171K/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 ...

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Weekend Offensive Security Engineer information

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$61.5K

$152.8K

$205.5K

How much do weekend offensive security engineer jobs pay per year?

As of Jul 18, 2026, the average yearly pay for weekend offensive security engineer in the United States is $152,773.00, according to ZipRecruiter salary data. Most workers in this role earn between $143,000.00 and $158,500.00 per year, depending on experience, location, and employer.

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

AspectWeekend Offensive Security EngineerPenetration Tester
CertificationsOSCP, CEH, GPENOSCP, CEH, GPEN
Work EnvironmentPart-time, project-based, often remoteFull-time, consulting or in-house roles
Industry UsageSecurity firms, tech companies, freelanceSecurity firms, consulting, internal security teams

The Weekend Offensive Security Engineer and Penetration Tester roles share similar certifications and skills, focusing on identifying vulnerabilities. However, the Weekend Offensive Security Engineer typically works part-time or on a flexible schedule, often remotely, while Penetration Testers usually hold full-time positions. Both roles are vital in cybersecurity, but the engineer role emphasizes a flexible, project-based approach, whereas Penetration Testers often work within organizations or consulting firms on scheduled assessments.

Can you make $500,000 a year in cyber security?

A Weekend Offensive Security Engineer can potentially earn $500,000 annually with extensive experience, specialized skills, and certifications like OSCP or CISSP. High salaries are typically associated with senior roles, consulting, or leadership positions in cybersecurity, often requiring advanced technical expertise and a strong professional reputation.

What engineers make $500,000?

Senior offensive security engineers, especially those with extensive experience, advanced certifications like OSCP or CISSP, and expertise in penetration testing and security tools, can earn $500,000 or more annually. High compensation is often associated with roles in large organizations, consulting firms, or those with specialized skills in cybersecurity and offensive security strategies.

How much do offensive security engineers make?

Offensive security engineers typically earn between $80,000 and $150,000 annually, depending on experience, certifications, and location. Senior roles or those with specialized skills in penetration testing and security tools can command higher salaries, especially in high-demand markets.

Is 40 too old for cyber security?

Age is not a barrier to becoming a Weekend Offensive Security Engineer or working in cybersecurity. Many professionals successfully transition into cybersecurity roles at various ages, leveraging skills like problem-solving, continuous learning, and certifications such as CISSP or OSCP. Employers value experience and skills over age, and the field offers opportunities for lifelong learning and career growth.
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Weekend Offensive Security Engineer jobs near you
Senior Security Engineer, Offensive Security

Senior Security Engineer, Offensive Security

Datadog

New York, NY • On-site

$195K - $240K/yr

Full-time

Medical, Dental, Retirement, PTO

Re-posted 18 days ago

Datadog rating

9.6

Company rating: 9.6 out of 10

Based on 6 frontline employees who took The Breakroom Quiz

1st of 451 rated business services

Job description

Here at Datadog, we think about offensive security a little bit differently. We embrace automation and AI to run adversary simulations continuously across a massive cloud-native environment, and we expect our offensive engineers to build the tooling that makes that possible. We're looking for a Senior Security Engineer who can execute sophisticated red team operations, write the code that scales them, and take an AI-first approach to offensive security engineering.
At Datadog, we place value in our office culture - the relationships and collaboration it builds, and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them.
What You'll Do:
  • Plan and execute red team engagements end-to-end, simulating real-world threat actors across cloud infrastructure (AWS, GCP), Kubernetes, CI/CD pipelines, and corporate environments
  • Build and maintain custom offensive tooling, automation frameworks, and engagement infrastructure, treating offensive operations as a software engineering problem
  • Develop custom payloads and evasion capabilities tailored to Datadog's environment and modern defensive controls (EDR, SIEM, network monitoring)
  • Improve the efficiency of offensive operations through thoughtful use of automation and AI, accelerating reconnaissance, vulnerability analysis, and reporting workflows
  • Partner with the Detection & Response team on purple team exercises to validate detection logic, improve alert fidelity, and influence threat models
  • Translate offensive findings into concrete improvements by working directly with defensive security and engineering teams to close gaps

Who You Are:
  • You have 5+ years of hands-on experience in offensive security (red teaming, penetration testing, or adversary simulation) with a track record of operating against mature, well-defended environments
  • You write production-quality code (Python, Go, or similar), can build your own tools, and automate your workflows rather than relying exclusively on off-the-shelf frameworks
  • You have deep expertise in at least a two of the following areas: macOS security, Linux security, cloud platforms (AWS, GCP, Azure), Kubernetes, or CI/CD pipelines
  • You have experience developing evasion techniques against modern defensive controls and understand how detections work from the blue team side
  • You have strong communication skills, with the ability to convey complex offensive findings clearly and effectively to both technical and non-technical stakeholders
  • You are comfortable operating with ambiguity, scoping your own work, identifying what matters most, and driving projects from prototype to deployed and validated

Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That's okay. If you're passionate about technology and want to grow your skills, we encourage you to apply.
Benefits and Growth:
  • New hire stock equity (RSUs) and employee stock purchase plan (ESPP)
  • Continuous professional development, product training, and career pathing
  • Intradepartmental mentor and buddy program for in-house networking
  • An inclusive company culture, ability to join our Community Guilds (Datadog employee resource groups)
  • Free, global mental health benefits for employees and dependents age 6+
  • Competitive global benefits

Benefits and Growth listed above may vary based on the country of your employment and the nature of your employment with Datadog.
#LI-Hybrid
Datadog offers a competitive salary and equity package, and may include variable compensation. Actual compensation is based on factors such as the candidate's skills, qualifications, and experience. In addition, Datadog offers a wide range of best in class, comprehensive and inclusive employee benefits for this role including healthcare, dental, parental planning, and mental health benefits, a 401(k) plan and match, paid time off, fitness reimbursements, and a discounted employee stock purchase plan.
The reasonably estimated yearly salary for this role at Datadog is:
$195,000-$240,000 USD
About Datadog:
Datadog is the leading observability and security platform for the AI era, providing businesses with unified visibility across the technology stack to manage complexity at scale. It brings applications, infrastructure, data, models, and security into one place, using AI to detect and resolve issues before they impact customers. Trusted globally by Fortune 500 companies and high-growth AI leaders, Datadog enables businesses to move faster with clarity and confidence. Learn more about #DatadogLife on Instagram, LinkedIn, and Datadog Learning Center.
Equal Opportunity at Datadog:
Datadog is proud to offer equal employment opportunity to everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, and other characteristics protected by law. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. Here are our Candidate Legal Notices for your reference.
Datadog endeavors to make our Careers Page accessible to all users. If you would like to contact us regarding the accessibility of our website or need assistance completing the application process, please complete this form. This form is for accommodation requests only and cannot be used to inquire about the status of applications.
Privacy and AI Guidelines:
Any information you submit to Datadog as part of your application will be processed in accordance with Datadog's Applicant and Candidate Privacy Notice. For information on our AI policy, please visit Interviewing at Datadog AI Guidelines.

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