AI Red Teamer, Cybersecurity (Remote)

HandshakeRemote (USA)General & Administrative

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Opens the official Handshake careers page

Salary

$65 - $125 USD per hour

Job type

Contract

Work mode

Remote

Posted

5 Sept 2026

Status

Open · checked 7d ago

About this role

Role Overview

The AI Red Teamer, Cybersecurity position at Handshake is a remote, contract-based role designed for offensive security professionals who want to test and evaluate frontier artificial intelligence models. This opportunity suits experienced security practitioners who can analyze model-generated code and determine whether it provides meaningful assistance in real-world cyberattacks.

Key Responsibilities

Design technically grounded adversarial prompts to test model assistance across the entire cyber kill chain, from reconnaissance to data exfiltration.

Evaluate model-generated code and technical outputs for functional correctness and real-world exploitability.

Test model behavior across various offensive categories, including malware creation, vulnerability exploitation, and social engineering.

Simulate different attacker personas, ranging from opportunistic novices to advanced persistent threat operators.

Probe dual-use boundaries by testing how models respond to queries combining legitimate security research with offensive applications.

Test multi-turn and multi-step attack chains that transition from benign context to malicious requests.

Score responses using structured harm taxonomies and document findings with clear technical reasoning.

Contribute to building cybersecurity evaluation frameworks and collaborate with AI researchers and policy teams.

Requirements

Professional background in offensive security, red teaming, penetration testing, malware analysis, vulnerability research, threat intelligence, or incident response.

Proficiency in reading, writing, and evaluating code in languages such as Python, PowerShell, Bash, C, C++, or JavaScript.

Solid understanding of attack frameworks like MITRE ATT&CK and OWASP.

Ability to assess the functional correctness and real-world exploitability of generated technical outputs.

Hands-on experience utilizing various large language models such as ChatGPT, Claude, Gemini, or open-source alternatives.

Creative problem-solving abilities paired with strong ethical judgment and clear written communication skills.

Nice to Have

Relevant industry certifications including OSCP, OSCE, GPEN, GXPN, CRTO, CRTL, or CEH.

Active or previous security clearance.

Experience in exploit development, reverse engineering, or binary analysis.

Background in cloud, container, or infrastructure-as-code security.

Familiarity with machine learning attack surfaces, including prompt injection and training-data poisoning.

Experience building custom implants or command-and-control frameworks.

A proven bug-bounty track record or published CVEs.

Previous work in trust and safety, content moderation, or AI evaluation.

Skills and Tools

Python

JavaScript

C++

LLM

PowerShell

Bash

MITRE ATT&CK

OWASP

Salary and Benefits

Hourly pay rate ranging from $65 to $125 USD.

About the Company

Handshake connects millions of job seekers with thousands of educational institutions and employers worldwide. Handshake AI partners with frontier AI labs to build data solutions, publish benchmarks, and support advanced model training.

How to Apply

Interested candidates should visit the official Handshake careers page to submit an application for this remote position.

Skills and tech stack

Python JavaScript C++LLM

Questions candidates ask

What is the work arrangement for this role?

This position is remote within the United States or based out of Seattle, Washington, with flexible work arrangements.

What is the employment type?

This role is offered on a contract basis.

What hourly rate does the position offer?

The hourly compensation ranges between $65 and $125 USD.

What programming languages are required or useful?

Candidates should be able to read, write, and evaluate code in languages commonly used for offensive tooling, such as Python, JavaScript, C++, PowerShell, and Bash.

Does this role involve handling offensive cybersecurity content?

Yes, the position involves regular engagement with malware, exploit code, social engineering scenarios, and intrusion techniques within structured ethical guidelines.

Ready to apply?

The application is on the official Handshake careers page.

Apply on company site