---
title: 'AI Red Teamer, Cybersecurity (Remote) at Handshake'
canonical: 'https://feeny.ai/job/ai-red-teamer-cybersecurity-remote-handshake-united-states-5wsaqqbbgaj9'
type: 'job'
last_seen: '2026-09-09'
---

# AI Red Teamer, Cybersecurity (Remote) at Handshake

- **Company:** [Handshake](https://feeny.ai/companies/handshake)
- **Location:** United States
- **Employment:** contract
- **Work type:** remote
- **Posted:** 2026-09-05
- **Last confirmed live:** 2026-09-09
- **Apply:** https://jobs.ashbyhq.com/handshake/7f607c0b-291d-4c17-9897-6d8c5d35eb00

## Job description

## CYBERSECURITY RED TEAMER

Location: Seattle, WA, or Remote within the United States 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.

## WHY JOIN HANDSHAKE NOW

- 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 States

## ABOUT HANDSHAKE AI

Human data is core infrastructure for AI advancement. Frontier AI labs currently improve model capabilities through data-intensive post-training techniques. We believe spending on AI training data will increase three to five times over the next few years and continue growing as models expand into new domains.

Handshake AI supports frontier AI labs by working on their most complex data challenges at scale.

## 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.

This role requires you to think like an attacker who has access to a highly capable AI assistant. You will craft adversarial prompts and multi-turn interaction chains that simulate how real threat actors, ranging from inexperienced attackers to advanced persistent threat operators, might use LLMs to accelerate reconnaissance, weaponization, exploitation, lateral movement, persistence, and exfiltration.

You will then evaluate whether the model’s output is genuinely dangerous or merely surface-level noise.

Deep cybersecurity expertise is essential. Your value will come from being able to examine a model-generated payload, exploit chain, or attack plan and determine whether it would actually work, how much refinement it would require, and what type of attacker it could meaningfully assist.

This position may be performed from our Seattle location or remotely within the United States. Seattle-based and remote team members will collaborate closely through shared evaluation workflows, regular feedback, and virtual working sessions.

## WHAT YOU WILL DO

- Design technically grounded adversarial prompts that test whether models provide meaningful assistance across the cyber kill chain, from reconnaissance through exfiltration and impact
- Evaluate model-generated code and technical output for functional correctness, determining whether outputs represent real exploits, plausible attack tooling, or nonfunctional noise
- Test model behavior across offensive categories, including malware generation, vulnerability exploitation, social engineering, credential harvesting, privilege escalation, command-and-control infrastructure, and data exfiltration
- Probe dual-use boundaries by testing how models respond to queries that combine legitimate security research, penetration testing, and defensive operations with offensive applications
- Simulate attacker personas at varying skill levels, including opportunistic, intermediate, and advanced or APT-level actors
- Test multi-step and multi-turn attack chains, including scenarios in which early turns establish benign context before pivoting to malicious requests
- Score model responses using structured harm taxonomies and severity rubrics calibrated to real-world exploitability
- Document findings with clear technical reasoning, including what a response gets right, what it gets wrong, and what level of attacker it could realistically assist
- Contribute to the development and refinement of cybersecurity-specific evaluation frameworks and threat models
- Collaborate with red teamers, AI researchers, and policy teams to translate findings into actionable model improvements
- Stay current on evolving tactics, techniques, and procedures, CVEs, jailbreak techniques, and the intersection of AI and offensive security

## CORE QUALIFICATIONS

- 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
- Clear and precise written communication, including the ability to explain technical risk to nonspecialist audiences
- Strong ethical judgment and the ability to separate adversarial thinking from personal values
- Ability to work independently while collaborating effectively in a feedback-heavy, distributed environment

## NICE TO HAVE

- Relevant certifications, such as OSCP, OSCE, GPEN, GXPN, CRTO, CRTL, CEH, or similar
- Active or previous security clearance
- Experience with exploit development, reverse engineering, or binary analysis
- Background in cloud security, container security, or infrastructure-as-code attack surfaces
- Familiarity with AI and machine-learning attack surfaces, including prompt injection, model extraction, training-data poisoning, and adversarial examples
- Experience building or operating command-and-control frameworks, custom implants, or offensive tooling
- A bug-bounty track record or published CVEs
- Previous work in trust and safety, content moderation, or AI evaluation
- Familiarity with LLM APIs or evaluation tooling

## YOU MAY BE A STRONG FIT IF

- You have spent years breaking into systems and want to apply that mindset to testing AI models
- You can examine a model-generated reverse shell, phishing template, or privilege-escalation script and quickly determine whether it would work in a real environment
- You think in kill chains and attack graphs, not just individual prompts
- You understand that the difference between a useful coding assistant and a dangerous one often comes down to context, specificity, and operational detail
- You closely follow the offensive-security community and stay current when new techniques emerge
- You care about AI safety because you understand what can happen when powerful tools are used irresponsibly
- You can collaborate effectively with a team whether you are working from Seattle or remotely

## CONTENT NOTICE

This role involves regular and deliberate engagement with offensive cybersecurity content. You will create and evaluate scenarios involving malware, exploit code, social engineering, network-intrusion techniques, and other attack methodologies.

All work is conducted within a structured evaluation framework with strict ethical guidelines. Candidates must be able to engage with this material professionally, responsibly, and sustainably.

## About Handshake

## Company Overview
- **One-liner**: Handshake is the career network for the AI economy, connecting job seekers with internships, full-time roles, freelance gigs, and AI training work through a three-sided marketplace.
- **Entity Type**: Private (Series F; total funding $434M across 6 rounds)
- **Headquarters**: San Francisco, California, USA
- **Founded**: 2014
- **Founders**: Garrett Lord (CEO), Ben Christensen, Scott Ringwelski

## Core Business
- **Primary industry**: Career platform / Job marketplace / AI workforce infrastructure
- **Target customers**: B2C (job seekers, from students to experienced professionals) and B2B (employers including 100% of Fortune 500 and all foundational AI labs; also educational institutions)
- **Mission**: Expand access and improve outcomes for job seekers, helping the workforce stay ahead in the AI economy.

## Products & Services
- **Handshake Core Platform**: A three-sided marketplace connecting 25 million knowledge workers, 1,600+ schools, and 1 million employers. Features dynamic profiles, intelligent job matching, and interactive skill-building.
- **Handshake AI Enterprise**: AI-powered tools for employers and job seekers, including AI-driven matching, safety features, and pay management.
- **AI Trainer Gigs**: Paid, flexible, remote work for individuals to train and evaluate AI models (e.g., AI Evaluation Specialist, up to $40/hr) – no prior AI experience required.
- **Handshake Network**: Community events, career advice, and networking for students, experts, and professionals in AI and other fields.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed
- **Key Metric**: Total funding $434M (6 rounds); annual revenue $56.5M (LinkedIn estimate)
- **Notable Investors/Partners**: Board includes representatives from General Catalyst, Kleiner Perkins, EQT Ventures, True Ventures, and Niantic. Strategic partners include 100% of the Fortune 500 and foundational AI labs.
- **Growth Signals**: Headcount at 5,272 employees (+708.8% YoY per LinkedIn); 1M+ companies on platform; 25M users; expansion into AI trainer gig economy; new roles in HAI (Handshake AI Enterprise) such as Applied AI Engineer, AI Platform Engineer, and Forward Deployed Engineer.

## Competitive Advantages
- **Network effects**: The only three-sided marketplace linking students, employers, and educational institutions at scale.
- **AI-first positioning**: Deep integration of AI into job matching, skill-building, and new freelance training roles – creating a unique ecosystem for the AI economy.
- **Trusted by elite institutions**: 1,600+ partner schools and every Fortune 500 company provides unparalleled reach into early-career talent.

## Strategic Focus
- **AI economy expansion**: Building the “career network for the AI economy” – expanding beyond college students to all knowledge workers, and adding AI training gigs as a new revenue and engagement stream.
- **Product innovation**: Heavy investment in Handshake AI Enterprise (HAI), including AI matching, safety, and pay infrastructure.
- **Global scaling**: Offices in San Francisco, New York, UK, and Bangalore; operating in 32 countries.

## Why Work Here
- **Culture**: Values include “Students first,” “Leave nothing to chance,” “Own the outcome,” “Invent and reinvent,” and “Olympic pace.” Emphasis on ownership, urgency, and constant evolution.
- **Remote/Hybrid policy**: Many roles are based in San Francisco or New York, but some positions (e.g., Trust & Safety Specialist, Support Specialist) are remote in the US. Recent openings show both office and remote options.
- **Benefits**: Health & wellness support, financial support, time off, modern offices with meals, snacks, and social activities. Strong focus on career growth and learning.
- **Career growth**: Rapid headcount growth suggests ample internal mobility; roles range from engineering (ML, AI, data) to customer success, partnerships, and product management.

## Sources
1. [joinhandshake.com/about](https://joinhandshake.com/about/)
2. [joinhandshake.com/careers](https://joinhandshake.com/careers/)
3. [linkedin.com/company/team-handshake](https://www.linkedin.com/company/team-handshake)
4. [joinhandshake.com](https://joinhandshake.com/)

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