If you take pride in being right, not just being fast, this role will feel like home. Your work becomes training data for AI systems that thousands of students use every day. When you label behavior with precision, the product gets smarter. When labels drift, the model learns the wrong lesson.
LearnWith.AI builds AI-powered learning experiences using learning science, data analytics, and subject matter experts. This role exists to turn raw student session videos into high-accuracy, rubric-driven labels that the team can trust. You will watch recorded student sessions, identify key behavioral events, and apply strict rules to classify what happened and when. You will also review LLM pre-annotations, fix what is wrong, and document edge cases so engineers can improve the system.
This is not gig-style, random-task annotation. It is a steady queue in a single product domain, with direct feedback loops, calibration against gold standards, and progression based on accuracy and consistency. If you want clear expectations, measurable quality, and work that directly impacts model performance, we want to meet you.
This role exists so that student session videos are converted into ≥95%-accurate, time-precise labeled datasets that reliably signal when model performance improves or regresses.
Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.






It’s hard to qualify – on purpose. High standards mean every educator, leader and EdTech builder is at the top of their game.
Top performers earn what they’re worth. Six-figure education roles aren’t fantasy here – they’re the baseline for excellence.
Skills carry more weight that resumes here. Demonstrate learning mastery, AI fluency and passion for what’s next. That’s what counts.