Everyone is welcome at Handshake. We know diverse teams build better products and we are committed to creating an inclusive culture built on a foundation of respect for all individuals. We strongly encourage candidates from non-traditional backgrounds, historically marginalized or underrepresented groups to apply.

Your impact

As an AI Tutor, Education Specialist, you will help train and evaluate advanced AI systems in tasks related to educational content, pedagogy, curriculum design, and learning assessment. Your deep understanding of instructional theory, cognitive science, and classroom practice will guide the development of high-quality, accurate, and pedagogically sound outputs across a variety of student-facing use cases. This is an exciting opportunity to apply your educational expertise in a cutting-edge, interdisciplinary environment.

This is a contract remote position with variable time commitments. The services to be provided by the Contractor under this agreement are supplementary and not integral to the Handshake’s primary business operations. The Contractor’s services are distinct and separate from the core business activities of Handshake.

Your role

• Evaluate AI-generated educational content and provide expert feedback on pedagogy, structure, and clarity.
• Score and critique model outputs related to tutoring, instructional design, and assessment across K–12, higher ed, and lifelong learning domains.
• Collaborate with cross-functional teams to develop annotation standards and quality criteria for educational data.
• Help identify areas for improvement in AI behavior, such as cognitive scaffolding, differentiation, or culturally responsive pedagogy.
• Support the design and curation of realistic prompts, instructional materials, and assessments for training and fine-tuning purposes.
• Adapt to new task definitions and evolving rubrics as our product and models grow.

Your experience

• PhD in Education, Learning Sciences, Instructional Design, Curriculum & Instruction, Educational Psychology, or a related field.
• Deep understanding of pedagogical theory and learning design—especially with constructivist, inquiry-based, or evidence-based frameworks.
• Experience teaching or designing curriculum at the K–12, undergraduate, or graduate levels.
• Strong analytical, evaluative, and writing skills—able to assess content quality from both technical and instructional perspectives.
• Comfort working with digital tools and structured educational tasks (e.g., scoring rubrics, taxonomy frameworks, educational standards).
• Interest in the application of AI in education, with an open but critical perspective on its role in teaching and learning.

Bonus areas of expertise

• Research experience in learning science, ed tech, or cognitive assessment.
• Experience with online or adaptive learning platforms.
• Familiarity with Universal Design for Learning (UDL), Bloom’s Taxonomy, or similar models.
• Strong professional writing or instructional design portfolio.
• Experience mentoring educators or conducting pedagogical training.

Additional Requirements

• Availability to work evenings and weekends as needed.
• Ability to quickly adapt to new skills and evolving requirements.
• Personal device must support Windows 10 or macOS Big Sur 11.0 or later.
• Reliable access to a smartphone.

Location & Work Expectations

• Fully remote position.
• No visa sponsorship available.
• Not hiring in Wyoming or Illinois at this time.

Compensation range

• $40/hr - $70/hr

For cash compensation, we set standard ranges for all U.S.-based roles based on function, level, and geographic location, benchmarked against similar stage growth companies. In order to be compliant with local legislation, as well as to provide greater transparency to candidates, we share salary ranges on all job postings regardless of desired hiring location. Final offer amounts are determined by multiple factors, including geographic location as well as candidate experience and expertise, and may vary from the amounts listed above.

About us

Handshake is building the future of human data for AI.

We partner directly with top AI labs to power large language model (LLM) training and evaluation with high-quality, expert-generated data. As AI models become more sophisticated, the demand for specialized human input continues to grow—and Handshake is uniquely positioned to meet it. We power career platforms at 92% of the top U.S. universities, giving us direct access to verified expert talent across a wide range of domains.

Our AI team is rapidly building a new generation of human data products—from expert annotation platforms to AI interviewers and seamless payout infrastructure—all designed to accelerate research and improve model performance.

We’ve assembled a world-class team from YC, Notion, Scale, Coinbase, Palantir, and more, and we’re working directly with many of the world’s leading AI research labs. This is a unique opportunity to join a fast-growing team shaping the future of AI through better data, better tools, and better systems—for experts, by experts.

Handshake is committed to providing reasonable accommodations in our recruitment processes for candidates with disabilities, sincerely held religious beliefs or other reasons protected by applicable laws. If you need assistance or reasonable accommodation, please let your recruiter know during initial communications.