Top 25 Information security Jobs in Sheboygan, Wi

Penetration Tester (Ethical Hacker) - AI Trainer
DataAnnotation —Wisconsin
- $50 - $100 an hour
- Part-time
- Remote
- English
- Mid-level
- Bachelor's degree
- Flexible schedule
Quick Apply
Cybersecurity Technical Writer - AI Trainer
DataAnnotation —Wisconsin
- $50 - $100 an hour
- Part-time
- Remote
- English
- Mid-level
- Bachelor's degree
- Flexible schedule
Quick Apply
Digital Forensics Examiner - AI Trainer
DataAnnotation —Wisconsin
- $50 - $100 an hour
- Part-time
- Remote
- English
- Mid-level
- Bachelor's degree
- Flexible schedule
Quick Apply
Product Security Engineer - AI Trainer
DataAnnotation —Wisconsin
- $50 - $100 an hour
- Part-time
- Remote
- English
- Mid-level
- Bachelor's degree
- Flexible schedule
Quick Apply
Systems Engineer - Database Administration
ACUITY, A Mutual Insurance Company —Sheboygan, WI
- $100,000 - $140,000 a year
- Computer Science
- System design
- Research
- Disability insurance
- Health insurance
Application Security Engineer
H.W. Kaufman Group —United States
- Full-time
- Remote
- 5 years
- Salesforce
- Analysis skills
FBI Special Agent: Cybersecurity/IT Expertise
Federal Bureau of Investigation —United States
- $103,236 - $133,200 a year
- Full-time
- Doctoral degree
- Mid-level
- Master's degree
4d
FBI Special Agent: Information Systems & Process Management Expertise
Federal Bureau of Investigation —United States
- $103,236 - $133,200 a year
- Full-time
- Doctoral degree
- Mid-level
- Master's degree
4d

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Cybersecurity Technical Writer - AI Trainer
DataAnnotation —Wisconsin
Flexible schedule: choose which projects you take on and when you work, on your own computer, from the comfort of your own home.
$50 - $100 an hour
Quick Apply

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Cybersecurity Technical Writer - AI Trainer
DataAnnotation —Ohio
Flexible schedule: choose which projects you take on and when you work, on your own computer, from the comfort of your own home.
$50 - $100 an hour
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Digital Forensics Examiner - AI Trainer
DataAnnotation —Ohio
Flexible schedule: choose which projects you take on and when you work, on your own computer, from the comfort of your own home.
$50 - $100 an hour
Quick Apply

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information security jobs near sheboygan, wi

Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation -
Wisconsin

Quick Apply

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 Penetration Tester (Ethical Hacker) - 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

information security jobs in sheboygan, wi

Penetration Tester (Ethical Hacker) - AI Trainer

Cybersecurity Technical Writer - AI Trainer

Digital Forensics Examiner - AI Trainer

Product Security Engineer - AI Trainer

Systems Engineer - Database Administration

Application Security Engineer

FBI Special Agent: Cybersecurity/IT Expertise

FBI Special Agent: Information Systems & Process Management Expertise

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