Startups · AI

AI Red Teamer, Cybersecurity (Remote)

Handshake · Remote (USA) · Remote

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About Handshake

Backed by Kleiner Perkins and Lightspeed.

About the role

As a Cybersecurity Red Teamer, you will evaluate whether AI models can be manipulated into generating functional malware, viable exploit code, attack tooling, or step-by-step operational guidance that could give a threat actor meaningful assistance in carrying out cyberattacks. Your job is to find the gaps between what a model’s safety guardrails are intended to block and what a skilled adversary can actually extract.

What they're looking for

  • Professional experience in offensive security, penetration testing, red teaming, vulnerability research, malware analysis, threat intelligence, or incident response
  • Ability to read, write, and evaluate code in languages commonly used for offensive tooling, such as Python, PowerShell, Bash, C/C++, or JavaScript
  • Understanding of common attack frameworks, techniques, and procedures, including MITRE ATT&CK and OWASP
  • Ability to assess the functional correctness and real-world exploitability of model-generated technical output
  • Strong hands-on experience using multiple LLMs, such as ChatGPT, Claude, Gemini, or open-source models
  • Creative and adversarial problem-solving skills
More about this role

Work arrangement: Flexible, including part-time availability

Handshake was founded on a simple belief: everyone deserves a path to a great career, regardless of where they went to school or who they know. Today, we support 25 million job seekers, more than 1 million employers, and 1,600 educational institutions.

In 2025, we started Handshake AI and built the fastest-growing AI data business in history. We work directly with researchers at frontier AI labs to create evaluations, publish benchmarks, and push the boundaries of data. We have grown from $0 to approximately $1 billion in run rate and pay approximately $60 million to more than 30,000 individuals every month.

Shape how careers evolve in the AI economy at a global scale, with an impact your friends, family, and peers can see and feel

Partner closely with world-class AI labs, Fortune 500 companies, and leading educational institutions

Work with engineers, scientists, operators, and other professionals from organizations such as Palantir, Meta, and Scale AI, as well as former YC founders

Help build a massive, rapidly growing business with billions in revenue

Work from Seattle or remotely from anywhere within the United...

Read the full posting on Handshake's site ↗

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