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Remote Penetration Tester Trainee Jobs (NOW HIRING)

Apex Informatics

security engineer

Security Engineer 100% Remote contract We are seeking a highly skilled and motivated Security ... Hands-on experience with penetration testing and vulnerability assessment tools. * Expertise in ...

Bishop Fox

Red Team Consultant

As leaders in continuous offensive security and penetration testing, we deliver world-class ... We're seeking remote, US or Mexico-based hacking professionals focused on red teaming to join our ...

Bishop Fox

Senior Red Team Consultant

As leaders in continuous offensive security and penetration testing, we deliver world-class ... We're seeking remote, US or Mexico-based hacking professionals focused on red teaming to join our ...

Bishop Fox

Red Team Consultant

OR · On-site +1

As leaders in continuous offensive security and penetration testing, we deliver world-class ... We're seeking remote, US or Mexico-based hacking professionals focused on red teaming to join our ...

Bishop Fox

Senior Red Team Consultant

OR · On-site +1

As leaders in continuous offensive security and penetration testing, we deliver world-class ... We're seeking remote, US or Mexico-based hacking professionals focused on red teaming to join our ...

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Remote Penetration Tester Trainee information

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$22.5K

$119.9K

$168.5K

How much do remote penetration tester trainee jobs pay per year?

As of Aug 16, 2026, the average yearly pay for remote penetration tester trainee in the United States is $119,895.00, according to ZipRecruiter salary data. Most workers in this role earn between $96,000.00 and $141,000.00 per year, depending on experience, location, and employer.

What is the difference between Remote Penetration Tester Trainee vs Remote Security Analyst?

AspectRemote Penetration Tester TraineeRemote Security Analyst
CertificationsBasic cybersecurity certifications (e.g., CompTIA Security+)Security+ or equivalent; may include CISSP or CEH
Work EnvironmentHands-on testing in simulated or real environments, often under supervisionMonitoring, analyzing security systems, and incident response
Industry UsageEntry-level, training-focused role in cybersecurity firms or IT departmentsMid-level role in organizations managing security operations

While both roles focus on cybersecurity, a Remote Penetration Tester Trainee is primarily involved in learning and assisting with penetration tests, whereas a Remote Security Analyst monitors and analyzes security threats. The trainee role emphasizes skill development, while the analyst role involves ongoing security management.

What are some common challenges faced by remote penetration tester trainees, and how can they overcome them?

Remote penetration tester trainees often encounter challenges such as limited direct mentorship, communicating effectively with team members across different time zones, and maintaining focus in a home environment. To overcome these, it's helpful to proactively schedule regular check-ins with mentors, utilize collaborative tools for clear communication, and set up a dedicated workspace to stay productive. Engaging in online training communities and seeking feedback can also accelerate learning and help trainees feel more connected to their team.

What are the key skills and qualifications needed to thrive as a remote penetration tester trainee, and why are they important?

To thrive as a Remote Penetration Tester Trainee, you need foundational knowledge in networking, cybersecurity principles, and operating systems, often supported by coursework or entry-level certifications like CompTIA Security+. Familiarity with tools such as Kali Linux, Metasploit, Wireshark, and vulnerability scanners is typically required. Strong analytical thinking, problem-solving abilities, and effective written communication help you document findings and collaborate remotely with teams. These skills ensure you can identify and report security weaknesses efficiently, supporting organizational cybersecurity objectives in a remote environment.

What is a remote penetration tester trainee?

A Remote Penetration Tester Trainee is an entry-level cybersecurity professional who assists in testing computer systems, networks, and applications for vulnerabilities from a remote location. Trainees work under supervision, learning how to identify security weaknesses and suggest improvements. They use various tools and techniques to simulate cyberattacks, helping organizations strengthen their defenses against real threats. This role is ideal for those looking to start a career in ethical hacking or information security, offering hands-on experience and training in a remote work setting.
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Cities with the most Remote Penetration Tester Trainee job openings:

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Remote Penetration Tester Trainee jobs near you
Infographic showing various Remote Penetration Tester Trainee job openings in the United States as of August 2026, with employment types broken down into 90% Full Time, 8% Part Time, 1% Contract, and 1% Nights. Highlights an 97% Physical, 1% Hybrid, and 2% Remote job distribution, with an average salary of $119,895 per year, or $57.6 per hour.

Penetration Testing Team Lead

SkyePoint Decisions

Washington, DC • On-site, Remote

$130K - $160K/yr

Full-time

Re-posted 12 days ago

Job description

SkyePoint Decisions is a leading Cybersecurity Architecture and Engineering, Critical Infrastructure and Operations, and Applications Development and Maintenance IT service provider headquartered in Dulles, Virginia with operations across the U.S. We provide innovative enterprise-wide solutions as well as targeted services addressing the complex challenges faced by our federal government clients. Our focus is on enabling our clients to deliver their mission most efficiently and effectively – anytime, anywhere, securely. We combine technical expertise, mission awareness, and an empowered workforce to produce meaningful results.

This is a contingent position based upon contract win.

SkyePoint Decisions is seeking a Penetration Testing Team Lead to join our team supporting the Department of Education's (DoED) Federal Student Aid (FSA) Cybersecurity and Privacy Support Services (CPSS) in Washington, DC.

This is a remote position.

Responsibilities:

  • Plans, coordinates and leads red team and penetration testing engagements across FSA systems.
  • Oversees test planning, execution, and reporting.
  • Maintain tools (patches and upgrades), their environment and inventory used in pen testing/Red Team exercises.
  • Ensures alignment with NIST SP 800-115, MITRE ATT&CK, and DHS RVA standards.
  • Mentors junior testers and evaluates new testing tools.

Required Qualifications:

  • Bachelor's degree and 12+ years of experience in offensive security.
  • At least an active Secret level clearance.
  • At least one of these certifications: OSCP, OSCE, GXPN, CEH.
  • Experience with network, application, AWS cloud, and API testing in complex environments.
  • Must be a U.S Citizen.

Compensation:

Salary Range: $130,000-$160,000

The SkyePoint Decisions salary range for this position is a general guideline only. It represents an estimated range for this position and is just one piece of our total compensation package.

Salary at SkyePoint is determined by various factors, including but not limited to location, work schedule, the candidate's combination of education, knowledge, skills, competencies, and experience, as well as contract-specific affordability, market data and business considerations.

In addition to a competitive salary, SkyePoint offers benefits including a certification incentive program, PTO, floating federal holiday options, several insurance options including HMO and High Deductible plans with Health Savings Accounts [HSAs], Flex Spending Accounts [FSAs], Full Dental Plans, Vision, ST/LT Disability, Life Insurance, and 401k matched.

What We Can Offer You:

  • At SkyePoint, we go B.I.G. (beginning in GRATITUDE) by recognizing all we have and giving back to our employees, families, and communities. It instills a positive mindset that permeates all we do. By beginning in gratitude, SkyePoint can continue to spread living in gratitude each day.
  • Great Benefits: Several insurance options including HMO and High Deductible plans with Health Savings Accounts [HSAs], Flex Spending Accounts [FSAs], Full Dental Plans, ST/LT Disability, Life Insurance, floating federal holiday options, and 401k matched
  • Certificate Incentive Program: To promote professional development, we recognize and reward employees who obtain new certifications aligned with business needs.
  • Flexible Work Environment

SkyePoint Decisions is an established ISO 9001:2015 and ISO/IEC 27001:2013 certified small business and appraised at CMMI Level 3 for Services and Development. We possess a common vision of excellence and foster a collaborative team culture built upon individual performance and accountability. We invest in our people and systems to create value for our clients. It is the SkyePoint Way. We are grateful for the opportunity to work with exceptional people and give back to the communities we serve. Our employees value the flexibility at SkyePoint that allows them to balance quality work and their personal lives.

SkyePoint Decisions is a participating E-Verify Employer.

U.S. Citizenship is required for most positions.

Equal Opportunity Employer/Veterans/Disabled.

CCPA Disclosure Notice Here