Lead Penetration Tester
Alignerr • Remote • Posted 0 days ago
Education
Any
Type
Pay Rate
$60/task
Posted
0d ago
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About this Role
What You'll Do
- Plan and execute penetration tests across web applications, internal and external networks, and cloud infrastructure
- Identify, validate, and exploit vulnerabilities to demonstrate real-world impact
- Conduct post-exploitation analysis to assess the full scope and blast radius of discovered weaknesses
- Deliver clear, structured technical reports with actionable severity assessments and remediation guidance
- Challenge and validate defensive assumptions — test detection logic, not just defenses
- Support recurring red-team and purple-team engagements alongside security operations teams
About the Role
What if your ability to think like an attacker could directly make organizations more secure? We're looking for a Lead Penetration Tester to conduct sophisticated offensive security engagements — probing applications, networks, and cloud environments for vulnerabilities before the real adversaries do. This is a fully remote contract role built for experienced offensive security professionals who thrive on technical challenge, think creatively under pressure, and communicate findings with clarity and precision.
Who You Are
Must-Have: Nice to Have:
- Proven background in offensive security, penetration testing, or red teaming
- Hands-on experience with common exploitation frameworks, tools, and methodologies (Metasploit, Burp Suite, Cobalt Strike, or similar)
- Strong ability to think like an adversary and replicate real-world attack chains
- Skilled at writing structured, professional technical reports that non-technical stakeholders can act on
- Self-directed and reliable — you can manage engagements independently without hand-holding
- Offensive security certifications (OSCP, OSWE, OSEP, CRTO, or similar)
- Experience with cloud-specific attack paths (AWS, Azure, GCP)
- Background in red team operations, adversary simulation, or threat emulation
- Familiarity with purple team collaboration and detection engineering workflows
Why Join Us
- Fully remote — work from wherever you do your best work
- Freelance autonomy with consistent, substantive engagements
- Work on technically challenging targets across diverse environments
- Contribute findings that directly improve real-world security posture
- Potential for ongoing contract work and expanded engagements over time
Requirements
- Fluent proficiency in English (Written & Verbal)
- Reliable high-speed internet connection
- Bachelor's degree or equivalent professional experience
- Demonstrated expertise in Software Engineering
Compensation Analysis
What if your ability to think like an attacker could directly make organizations more secure? We're looking for a Lead Penetration Tester to conduct sophisticated offensive security engagements — probing applications, networks, and cloud environments for vulnerabilities before the real adversaries do. This is a fully remote contract role built for
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Frequently Asked Questions
What is the assessment actually like?
Notoriously strict. Alignerr uses TestGorilla for role-specific timed tests — a blank coding environment for engineers, rigorous grammar and fact-checking for writers. There is almost no hand-holding. The critical catch: this is essentially a one-shot process. Fail or abandon the assessment, and you are typically locked out of that role permanently with no option to retake.
How quickly can I start earning after I pass?
Not immediately. Even after passing the assessment and completing identity verification (via Persona) and billing setup (via Deel), you may sit in a waiting pool for weeks or months. You only start earning when a project matching your specific skills launches and you are officially assigned. Do not plan around Alignerr income until you are actively on a project.
Is there a community?
Yes — and it is one of Alignerr's genuine strengths. Once assigned to a project, you are added to Slack channels where you can ask questions, get rubric clarifications from admins, and talk to other AI trainers. This is rare in AI training and makes a real difference when guidelines are ambiguous or change mid-project.
What does the work actually look like?
It is practical, hands-on data work. You might be recording short videos, categorizing images, rating text responses, or analyzing data. The tasks are designed to be short and distinct—typically 5-60 minutes per task.
How flexible is the schedule?
Extremely. This is true "log in and work" flexibility. You can usually work for 20 minutes or 4 hours depending on your availability. There are rarely minimum hour requirements, making it ideal for side income.
Is there an interview?
Usually, no. Hiring for these roles is almost entirely based on passing an automated assessment or "qualification" task. If you pass the test, you get access to the work.
What is the barrier to entry?
Alignerr is known for difficult technical assessments. You must pass a timed test in your specific domain (e.g., Python, Physics, or Language) before you are eligible for any paid projects.