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Lead Penetration Tester
Alignerr • Remote
Education
Not stated
Type
Hourly
Pay Rate
$40–$80/hr
Listed
Today
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Check Listing → ⚡ Boost your chances - Optimize your resume with Rezi.aiAbout this role
From the Alignerr listing
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
Why this 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
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Common questions
Does Alignerr have a trainer community?
Yes, and it's a genuine strength. Once you're assigned to a project, you join Slack channels where you can get rubric clarifications from admins and talk to other trainers. That kind of support is rare in AI training and matters most when guidelines are ambiguous or shift mid-project.
How hard is the Alignerr assessment?
Hard, and unforgiving. Alignerr uses TestGorilla for timed, role-specific tests: a blank coding environment for engineers, strict grammar and fact-checking for writers. Treat it as one shot. Failing or abandoning it typically locks you out of that role permanently, with no retake.
What does task-based AI training work look like?
Practical, hands-on data work: recording short videos, categorizing images, rating text responses, or analyzing data. Tasks are designed to be short and distinct, typically 5 to 60 minutes each.
What does asynchronous AI training work mean in practice?
No set hours, no check-ins, no meetings. You log in when you want, pick up an available task, complete it, and submit; nobody is waiting on you in real time. That's different from remote employment, where you're expected online during business hours. The tradeoff: you're competing with others for available tasks, so an empty queue means there's simply nothing to do until more work is released.
What does Software Engineering work look like for a Lead Penetration Tester?
Tasks here are scoped to Software Engineering, not generic labeling. As a Lead Penetration Tester, expect to draw on real domain judgment (evaluating outputs, correcting errors, or providing expert reasoning specific to Software Engineering) rather than following a one-size-fits-all rubric. If you don't have hands-on Software Engineering background, this is likely not the right listing to start with.
What specific skills does this listing call for?
AI Training is named directly in the listing. If you don't have hands-on experience with this, expect the screening process to test for it directly rather than accepting adjacent experience as a substitute.
How much does this specific role pay?
This listing is posted at $40–$80/hr, an hourly rate. The range reflects experience level and negotiated terms, not a placeholder, so where you land in it depends on your background and the assessment. Pay can change between when we last checked the listing and when you apply, so confirm the current number on the platform's own application page before committing time.
What happens when I click Apply on this listing?
You'll be taken to Alignerr's external site to complete your application there. This listing links through a referral, but the process is identical to applying directly; the link just routes you correctly. Create an account on their site and follow their onboarding steps.
What is the barrier to entry for Alignerr?
A difficult, timed technical assessment in your specific domain, like Python, physics, or language. Passing it is required before you're eligible for any paid projects.