---
title: 'AI Red Teamer (LLM Generalist) at Handshake'
canonical: 'https://feeny.ai/job/ai-red-teamer-llm-generalist-handshake-seattle-nd0pg32zvw43'
type: 'job'
last_seen: '2026-09-16'
---

# AI Red Teamer (LLM Generalist) at Handshake

- **Company:** [Handshake](https://feeny.ai/companies/handshake)
- **Location:** Seattle, WA
- **Employment:** full-time
- **Work type:** onsite
- **Posted:** 2026-09-10
- **Last confirmed live:** 2026-09-16
- **Apply:** https://jobs.ashbyhq.com/handshake/e15e3244-06f9-4c41-96c6-8860ad7594c5

## Job description

AI Red Teamer (LLM Generalist) Location: Seattle, WA (candidates must reside in the Seattle metro area or be willing to relocate prior to start) Type: Contract, 40 hours per week

## About the Role

As an AI Red Teamer, you will stress-test large language models by intentionally trying to break them. Rather than checking whether an answer is correct, you will design creative, adversarial prompts that expose vulnerabilities: unsafe content, bias, broken guardrails, hallucinations, prompt injection weaknesses, and unexpected behaviors. Your work directly supports AI safety and model robustness for leading research labs. This is a generalist red teaming role. You will probe models across the full spectrum of risk categories, including content safety, CBRN (chemical, biological, radiological, nuclear), cybersecurity, persuasion and influence operations, child safety, self-harm, over-companionship, and regulatory compliance. Red teaming may span text, image, voice, and agentic model capabilities depending on project needs. This role requires creativity, curiosity, and an ability to think like an adversary while operating with strong ethical judgment. Day-to-Day Responsibilities

- Craft creative prompts and multi-turn scenarios to stress-test AI guardrails across diverse risk categories
- Discover ways around safety filters, restrictions, and defenses using jailbreak, evasion, and prompt injection techniques
- Explore edge cases to provoke disallowed, harmful, or incorrect outputs
- Evaluate and score model responses against structured harm taxonomies and severity rubrics
- Document experiments clearly, including what you tried, why you tried it, and what it revealed
- Review and refine adversarial prompts generated by other team members
- Contribute to harm taxonomy development, calibration exercises, and inter-rater reliability work
- Collaborate with engineers, data scientists, and researchers to share findings and strengthen defenses
- Work with potentially disturbing content on a regular basis (see Content Warning below)
- Stay current on jailbreaks, attack methods, and evolving model behaviors

Desired Capabilities Core

- Strong hands-on experience using multiple LLMs (ChatGPT, Claude, Gemini, open-source models, etc.)
- Intuition for crafting adversarial prompts; familiarity with jailbreak or evasion techniques is a strong plus
- Creative, adversarial problem-solving skills
- Clear and thoughtful written communication
- Strong ethical judgment and the ability to separate adversarial thinking from personal values
- Self-directed, collaborative, and comfortable in feedback-heavy environments
- Curiosity, persistence, and comfort with frequent failure in experimentation

## Nice to Have

- Familiarity with Python or other scripting languages
- Experience working with LLM APIs or evaluation tooling
- Comfort with structured data annotation and rubric-based scoring
- Prior work in trust and safety, content moderation, QA, or security research
- Subject matter expertise in any high-risk domain (cybersecurity, chemistry, biology, medicine, law, finance, etc.)

You Will Thrive Here If

- You treat every model response as a hypothesis to challenge
- You can switch between creative free-association and rigorous documentation in the same session
- You go deep into unusual interests (fandoms, niche internet cultures, gaming exploits, Wikipedia rabbit holes, etc.)
- You come from a creative background: writing, visual art, improv, puzzle design, or similar
- You are energized by finding the thing nobody else thought to try
- You are genuinely passionate about AI and follow the space closely

Content Warning This role involves regular and deliberate exposure to harmful content. You will encounter and intentionally generate content involving violence, self-harm, hate speech, sexually explicit material, child safety scenarios, and other categories of harmful output as part of structured adversarial testing. Candidates must be able to engage with this material professionally and sustainably. Support resources are available.

## About Handshake AI

Handshake AI partners with leading AI research labs to make models safer and more robust. Our red teaming operations help identify vulnerabilities before they reach users, contributing directly to the responsible development of frontier AI systems.

## 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/)

## Other roles at Handshake

- [AI Red Teamer (LLM Generalist) - Remote](https://feeny.ai/job/ai-red-teamer-llm-generalist-remote-handshake-united-states-nsv8rhpz17yq) — United States
- [VP of Product, Handshake AI](https://feeny.ai/job/vp-of-product-handshake-ai-handshake-san-francisco-vcwzbdk0rb2x) — San Francisco, CA
- [Director, Central Operations](https://feeny.ai/job/director-central-operations-handshake-san-francisco-06qyp36sb5ym) — San Francisco, CA
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- [Senior Recruiter](https://feeny.ai/job/senior-recruiter-handshake-seattle-rkb3p1en91hq) — Seattle, WA
- [Lead Recruiter, India](https://feeny.ai/job/lead-recruiter-india-handshake-india-vsgct8sg58ng) — India
- [Senior Director - AI Commercial Counsel](https://feeny.ai/job/senior-director-ai-commercial-counsel-handshake-san-francisco-rr3c2az2ts06) — San Francisco, CA
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