Top 55 Cyber Systems Operations Jobs in Milwaukee, WI

Cybersecurity Analyst - AI Trainer
DataAnnotation —Wisconsin
- $50 - $100 an hour
- Part-time
- Remote
- English
- Mid-level
- Bachelor's degree
- Flexible schedule
Quick Apply
11d
Sr Threat Hunt Engineer
Northwestern Mutual —Milwaukee, WI
- $118,960 - $178,440 a year
- Full-time
- Remote
- Computer Science
- System design
- Analysis skills
- Flexible schedule
5d
Office Assistant III
We Energies (WE) —Milwaukee, WI
- $23.86 - $39.65 an hour
- Mid-level
- Office
- Travel
7d
Operations Technology Cybersecurity Analyst
Silgan Containers Mfg Corp —Brookfield, WI
- Full-time
- System design
- Mid-level
- 3 years
- AD&D insurance
- Paid holidays
Paralegal, Subpoena Team
Fiserv —Milwaukee, WI
- Full-time
- Military
- Research
- Mid-level
- Free parking
- Paid parental leave
Compliance Lead
Johnson Controls —Milwaukee, WI
- $100,000 - $150,000 a year
- Full-time
- Hybrid work
- 6 years
- Office
- Bachelor's degree
- Paid holidays
- Health insurance
Vice President Information Technology
Trusted Fraternal Life —Milwaukee, WI
- Bachelor's degree
- Contracts
- Business Administration
Quick Apply
NETWORK ARCHITECT
Milwaukee County Transit System —Milwaukee, WI
- $82,500 - $97,000 a year
- Full-time
- 5 years
- Windows
- Supervising experience
12d
Cyber Partner Activation Manager
Rockwell Automation —Milwaukee, WI
- $130,160 - $195,240 a year
- Full-time
- Hybrid work
- Engineering
- Office
- 8 years
- Health insurance
- Dental insurance
12d
Lead Cyber Threat Intelligence Analyst
U.S. Bank National Association —Brookfield, WI
- $126,820 - $149,200 a year
- Full-time
- 5 years
- Writing skills
- Office
- Paid holidays
- Disability insurance
IT Program Manager - Cyber Compliance
Eaton —Menomonee Falls, WI
- $130,000 - $190,000 a year
- Hybrid work
- Background check
- Office
- Bachelor's degree
- Retirement plan
6d
Cybersecurity Operations Lead
Racine County —Racine, WI
- $32.93 - $46.80 an hour
- Full-time
- Management
- Computer Science
- System design
10d
Insurance Risk Manager
Phoenix Investors —Milwaukee, WI
- Full-time
- Computer literacy
- Mid-level
- Microsoft Office
Quick Apply
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
11d
Cybersecurity Technical Writer - AI Trainer
DataAnnotation —Wisconsin
- $50 - $100 an hour
- Part-time
- Remote
- English
- Mid-level
- Bachelor's degree
- Flexible schedule
Quick Apply
11d
Digital Forensics Examiner - AI Trainer
DataAnnotation —Wisconsin
- $50 - $100 an hour
- Part-time
- Remote
- English
- Mid-level
- Bachelor's degree
- Flexible schedule
Quick Apply
11d
Business Continuity Program Manager
Children's Wisconsin —Milwaukee, WI
- Full-time
- Hybrid work
- Microsoft Word
- Microsoft Excel
- Hospital
Infrastructure Engineer - Cloud
Deloitte —Milwaukee, WI
- $93,000 - $191,000 a year
- Overtime
- Azure
- Computer Science
- 5 years
4d
Cyber Digital Trust and Online Safety Specialist/Sr Consultant
Deloitte —Milwaukee, WI
- $105,400 - $207,800 a year
- Full-time
- Up to 50% travel
- 5 years
- Master's degree
Agentic Identity Security Consultant
Accenture —Milwaukee, WI
- $59,100 - $205,800 a year
- Full-time
- Hybrid work
- Azure
- System design
- Mid-level
- Paid holidays
- Disability insurance

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Cyber Systems Operations jobs near Milwaukee, WI

Cybersecurity Analyst - AI Trainer

DataAnnotation -
Wisconsin

Quick Apply

Job Details

Part-time | Full-time | Contract
$50 - $100 an hour
11 days ago

Benefits

Flexible schedule

Qualifications

Software coding
English
Programming languages

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 Analyst - 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

Cyber Systems Operations jobs in Milwaukee, WI

Cybersecurity Analyst - AI Trainer

Sr Threat Hunt Engineer

Office Assistant III

Operations Technology Cybersecurity Analyst

Paralegal, Subpoena Team

Compliance Lead

Vice President Information Technology

NETWORK ARCHITECT

Cyber Partner Activation Manager

Lead Cyber Threat Intelligence Analyst

IT Program Manager - Cyber Compliance

Cybersecurity Operations Lead

Insurance Risk Manager

Penetration Tester (Ethical Hacker) - AI Trainer

Cybersecurity Technical Writer - AI Trainer

Digital Forensics Examiner - AI Trainer

Business Continuity Program Manager

Infrastructure Engineer - Cloud

Cyber Digital Trust and Online Safety Specialist/Sr Consultant

Agentic Identity Security Consultant

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