AI Policy Generalist

About Handshake

Handshake was founded on a simple belief that everyone deserves a path to a great career, regardless of where they went to school or who they know. Today, we power 25 million job seekers, 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 frontier AI lab researchers to create evaluations, publish benchmarks, and push the boundary of data. We’ve grown from $0 to ~$1B run rate and pay ~$60M to over 30K individuals every month.

About the Role

As an AI Policy Generalist, you will turn complex customer policies into consistent, well-reasoned evaluations of AI model behavior.

You will read user requests, model responses, and relevant conversation history, then determine which policy category best applies. The most interesting cases will not have obvious answers. Two examples may look almost identical until a single word, contextual detail, or difference in intent changes the correct classification.

We are looking for people who enjoy splitting hairs in a healthy way. You form clear opinions, explain precisely why two cases should be treated differently, challenge interpretations respectfully, and change your mind when better evidence emerges. You understand that productive disagreement is not about winning an argument. It is how a team finds the most accurate and consistent interpretation.

This is not rote annotation. Policies cannot anticipate every possible edge case, and good evaluators do not apply them mechanically. You will balance the policy’s text and intent with customer expectations, conversation context, precedent, and team calibration.

The subject matter will vary. One project may involve distinguishing benign assistance from meaningful facilitation of harm. Another may require evaluating whether an interaction reflects ordinary emotional support or unhealthy reliance. A third may focus on nuanced boundaries within sexual-safety policy. Success requires learning each customer’s framework on its own terms rather than carrying assumptions from one domain into another.

What You Will Do

• Learn new customer policies, definitions, taxonomies, and evaluation rubrics quickly
• Evaluate user requests and AI model responses within the full relevant conversation context
• Distinguish between closely related labels, severity levels, and policy boundaries
• Select the most defensible classification when a case is genuinely ambiguous
• Write concise, evidence-based rationales that cite relevant policy language and conversation details
• Identify policy gaps, contradictions, unclear definitions, and emerging edge cases
• Raise thoughtful questions when existing guidance does not resolve a case
• Participate actively in calibration discussions with evaluators, project leads, policy teams, and researchers
• Challenge interpretations respectfully and update your judgment when new guidance or stronger reasoning emerges
• Apply customer policy consistently without substituting personal beliefs for the policy standard
• Maintain accuracy and attention to detail across repeated evaluations
• Incorporate feedback quickly and apply clarified guidance to future work
• Help improve evaluation frameworks, examples, decision rules, and quality standards
• Move effectively between projects covering different policy domains and customer needs

You May Be a Fit If

• You enjoy making precise distinctions between cases that other people might consider equivalent
• You notice when one word, contextual detail, or change in intent materially affects the answer
• You can hold a strong opinion without becoming attached to being right
• You explain judgment calls clearly enough that another person can audit your reasoning
• You ask productive questions when a policy is ambiguous instead of guessing or forcing certainty
• You can separate your personal views from the standard a customer has asked you to apply
• You are comfortable discussing disagreement directly, respectfully, and without making it personal
• You can follow the letter of a policy while also understanding its purpose and underlying logic
• You remain careful and consistent during repetitive, feedback-heavy work
• You learn unfamiliar subject matter quickly and know when additional context is needed
• You are intellectually curious, self-directed, and comfortable working in a fast-changing environment
• You communicate clearly and precisely in writing
• You treat sensitive information and difficult subject matter with maturity and sound judgment

Strong candidates may come from quality assurance, research, editing, law, teaching, operations, trust and safety, content moderation, social science, policy, investigations, compliance, customer support, or other fields that require careful interpretation and defensible decision-making. We care more about how you reason than where you learned to reason.

Nice to Have

• Experience evaluating or comparing outputs from ChatGPT, Claude, Gemini, or other language models in a professional capacity
• Prior work in AI evaluation, data annotation, RLHF, model quality, trust and safety, policy operations, or content moderation
• Experience applying detailed rubrics, taxonomies, regulatory language, editorial standards, or quality frameworks
• Familiarity with calibration sessions, inter-rater agreement, quality audits, or adjudication workflows
• Experience writing policy guidance, decision trees, evaluation examples, or structured rationales
• Comfort working with long conversations, incomplete context, and conflicting evidence
• Familiarity with AI safety, responsible AI, or the ways language models can assist, mislead, or cause harm

Prior AI evaluation experience is helpful, but it is not required.

Sensitive-Content Notice

This role involves regular and deliberate engagement with sensitive material. Depending on the project, evaluations may include sexual content, emotional distress, self-harm, suicide, violence, weapons, abuse, exploitation, discrimination, and other potentially disturbing subjects.

The work is conducted within structured evaluation frameworks and professional guidelines. Candidates must be able to engage with this material carefully, responsibly, and sustainably while maintaining sound judgment and consistent work quality.

Role Details

• Location: Seattle, WA
• Compensation: $45-55
• Employment classification: W-2
• Schedule: 8AM - 5PM PT
• Weekly commitment: M-F