Top 218 Penetration testing Jobs in Maryland

Cybersecurity Director - AI Trainer
DataAnnotation —Baltimore, MD
- $50 - $100 an hour
- Part-time
- Remote
- English
- Mid-level
- Bachelor's degree
- Flexible schedule
Quick Apply
Application Security Engineer - AI Trainer
DataAnnotation —Silver Spring, MD
- $50 - $100 an hour
- Part-time
- Remote
- English
- Mid-level
- Bachelor's degree
- Flexible schedule
Quick Apply
Security Architect - AI Trainer
DataAnnotation —Severn, MD
- $50 - $100 an hour
- Part-time
- Remote
- English
- Mid-level
- Bachelor's degree
- Flexible schedule
Quick Apply
Testing and Evaluation Specialist
National Security Agency —Fort Meade, MD
- $105,262 - $192,764 a year
- 8 hour shift
- Doctoral degree
- Computer Science
- No experience needed
11d
Research Scientist, Penetration Testing
Harbor Labs —Baltimore, MD
- Full-time
- Computer Science
- HIPAA
- Mid-level
Penetration Tester
Booz Allen Hamilton —Fort Meade, MD
- $86,900 - $198,000 a year
- Full-time
- Computer Science
- Mid-level
- Office
- Health insurance
- Flexible spending account
Penetration Tester / Ethical Hacker
CyberLinx Solutions LLC —Fort Meade, MD
- Full-time
- APIs
- Senior level
Quick Apply
Penetration Tester - Cyber Engineer
CACI —Aberdeen Proving Ground, MD
- $90,300 - $189,600 a year
- Full-time
- Analysis skills
- Bachelor's degree
- Travel
- Health insurance
IT Security Specialist - Penetration Tester
ATTAINX INC —Silver Spring, MD
- $125,000 - $145,000 a year
- Full-time
- Hybrid work
- Azure
- 5 years
- Research
- Disability insurance
- Health insurance
6d
Testing and Evaluation Specialist - Mid to Experienced Level (Maryland)
US National Security Agency/Central Security Service —Fort Meade, MD
- $105,262 - $192,764 a year
- 8 hour shift
- Background check
- Computer science
- Doctoral degree
11d
Penetration Tester, Senior
Navstar, Inc. —Annapolis Junction, MD
- $150,000 - $190,000 a year
- 11+ years
- Java
- Bachelor's degree
- Paid holidays
- Disability insurance
Penetration Tester - TS/SCI with Polygraph
General Dynamics Information Technology —Bethesda, MD
- $172,144 - $232,900 a year
- Computer Science
- Research
- Office
- Paid time off
- 401(k) matching
9d
Vulnerability Assessment Analyst
Accenture Federal Services —Columbia, MD
- $143,200 - $171,300 a year
- Mid-level
- Analysis skills
- US work authorization
Penetration Tester (Skill Level 3)
Strategic Analytix —Fort Meade, MD
- $0 a year
- Full-time
- Computer Science
- Research
- Bachelor's degree
Quick Apply
System Vulnerability Analyst
National Security Agency —Fort Meade, MD
- $105,262 - $192,764 a year
- 8 hour shift
- Doctoral degree
- Computer Science
- No experience needed
1d
DIGITAL NETWORK EXPLOITATION ANALYST (Levels I-IV)
BTS Software Solutions —Annapolis Junction, MD
- $120,000 - $260,000 a year
- Mid-level
- Under 1 year
- Health insurance
- Paid time off
Penetration Tester with Splunk
MANTECH —Fort Meade, MD
- Full-time
- Computer Science
- Bachelor of Science
- Office
Security Controls Assessor (SCA)
Interclypse, Inc. —Annapolis Junction, MD
- Full-time
- In-person
- Senior level
- Paid jury duty
- Health savings account
Cyber Network Professional
National Security Agency —Fort Meade, MD
- $87,362 - $153,082 a year
- 8 hour shift
- 18 years or older
- Computer science
- Doctoral degree
16h
Incident Responder
Leidos —Suitland, MD
- $107,900 - $195,050 a year
- Full-time
- 5 years
- Java
- Master's degree

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penetration testing jobs near maryland

Cybersecurity Director - AI Trainer

DataAnnotation -
Baltimore, MD

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Job Details

Part-time | Full-time | Contract
$50 - $100 an hour

Benefits

Flexible schedule

Qualifications

Software coding
English

Full Job Description

DataAnnotation is committed to creating quality AI. Help train AI chatbots while gaining the flexibility of remote work and choosing your own schedule.

We are looking for an existing Cybersecurity Director - AI Trainer to help train AI models. Cybersecurity platforms are increasingly powered by AI — but these systems still need practitioners with real-world experience to validate whether the outputs actually hold up in practice. That's where you come in.

You'll work closely with state-of-the-art AI models on tasks like evaluating AI-generated security content, solving technical security problems, and providing feedback that directly shapes how these systems reason about real-world threats and defenses. You can fit this work alongside a full-time role, or treat it as your primary focus, choosing projects and schedules that align with your availability and goals.

To get started, once you sign up for an account, you'll take a short assessment (this serves as our version of an interview). If you pass, you'll receive an email confirmation and paid work will become available to you through our platform.

Advantages of contracting with us:

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand.
Flexible schedule: choose which projects you take on and when you work, on your own computer, from the comfort of your own home.
Competitive pay: projects are paid hourly at $50 to $100 USD per hour. Opportunities for higher bonus rates available for certain projects.
Impact: help shape the future of AI technologies built for cybersecurity.

Responsibilities:

Evaluate AI-generated cybersecurity content — including threat analysis, vulnerability assessments, and offensive security techniques — for real-world accuracy and validity.
Design and solve security-focused technical problems used to train AI systems.
Write clear technical explanations and security-relevant code.
Provide feedback that directly shapes the next generation of AI security models.

Qualifications:

2+ years of hands-on experience in a cybersecurity role — such as penetration testing, red teaming, incident response, detection engineering, DFIR, malware analysis, threat intelligence, or adjacent fields, including government or military cyber operations.
Some coding experience required; comfort navigating and patching a codebase is key.
Fluency in English (native or bilingual level) with strong writing skills.
A bachelor's degree is preferred.
Cybersecurity certifications are a plus (e.g., OSCP, CRTO, GREM, GCFA, CEH, and similar).

Note: Payment is made via PayPal. We will never ask for any money from you. This job is only available to those in the US, Canada, UK, Ireland, Australia, and New Zealand.

Quick Apply

Refine Your Search

penetration testing jobs in maryland

Cybersecurity Director - AI Trainer

Application Security Engineer - AI Trainer

Security Architect - AI Trainer

Testing and Evaluation Specialist

Research Scientist, Penetration Testing

Penetration Tester

Penetration Tester / Ethical Hacker

Penetration Tester - Cyber Engineer

IT Security Specialist - Penetration Tester

Testing and Evaluation Specialist - Mid to Experienced Level (Maryland)

Penetration Tester, Senior

Penetration Tester - TS/SCI with Polygraph

Vulnerability Assessment Analyst

Penetration Tester (Skill Level 3)

System Vulnerability Analyst

DIGITAL NETWORK EXPLOITATION ANALYST (Levels I-IV)

Penetration Tester with Splunk

Security Controls Assessor (SCA)

Cyber Network Professional

Incident Responder

I want to receive the latest job alert for penetration testing in maryland

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