Randi Loveland has spent her career making math feel less like a wall and more like a staircase.
From her home in Albertville, Alabama, she writes curriculum for math teachers that’s built for classrooms that need it most. There are too few teachers with a wide range of needs, but there’s too much on their plates.
“One of the biggest issues in education is that there’s not enough teachers to address the needs of every student. Not enough teachers to take care of those with disabilities, to help those that are doing better, to excel,” she said.
Her fix, honed over years of work, is the same one she brings to every hard problem: break it down step by step until the hard thing becomes the next thing.
That same instinct is what she now brings to Outlier, where she contributes to evaluating and improving the AI models that are increasingly being used to meet students where they are.
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It All Started With A Reddit Thread and a LinkedIn Post
Randi first heard about Outlier through a Reddit thread. She Googled the platform, found a LinkedIn post looking specifically for a mathematics specialist, and applied.
“When I started working on Outlier, it made me feel like I was doing something that impacted the world,” she says, “because AI is really the future that we’re all going towards.”
Randi’s path into contributor work is more common than it might sound. A 2025 Oxford Economics study of the data annotation industry found that 84% of contributors hold at least a bachelor’s degree (roughly double the share in the general US workforce) and that the industry supported nearly 200,000 earning opportunities in the US in 2024 alone. The people shaping today’s AI systems are often specialists in fields far from tech such as educators, scientists, writers, and clinicians each bringing their domain expertise to the models in the hours their primary work doesn’t fill.
Writing Curriculum, Writing for Models
When Randi writes curriculum, she is writing for the moms working through a lesson at the kitchen table, the teachers picking up a new standard, and business owners trying to run their business more efficiently. Every lesson is an exercise in empathy, which means assuming nothing, skipping no step.
“I write for moms, sometimes educators, or business owners,” she says. “When I write curriculum for students, my focus is breaking things down into pieces so that they’re able to understand every step and see exactly what I’m doing.”
Her Outlier work mirrors that same discipline. “We write instructions for the model, for how it should respond to different questions, and how it should address different things, and the language it should use so that it’s speaking in a way that those who use it can understand it.”
Randi’s favorite tasks are education evaluations which look at how models respond to problems in her field, math. It’s the place where her two lives meet: the teacher who has spent a career lowering the ceiling on what students can reach, and the contributor who is now doing the same thing inside the model.
A Christmas for Other Families
Math is often described as cold. Randi’s story is not.
This winter, she used part of her Outlier income to sponsor a couple of families’ dinners for Christmas.
“We were able to provide Christmas dinner and presents for all the children,” she says, “which is really fun and rewarding to do.”
Oxford Economics found similar trends in its survey of contributors. For the majority, income and flexibility are the two strongest draws of the work: the ability to put expertise to use on a schedule that fits around the rest of life, and in service of the things that matter most to them. For Randi, that meant two families, one Christmas, a set of choices she got to make herself.
Changing the Perception of Math
When Randi talks about the future, she talks about students.
“What makes me the most excited about AI is how it’s going to impact students everywhere,” she says. “With Outlier, I’m doing something even deeper because I’m ensuring the models are exactly what the students need. I’m making sure that it’s accurate. It’s teaching them in a way that they should learn.”
Math is the subject students fear first and avoid longest. If a model can meet a struggling student with patience, accuracy, and a clear next step, it can do what Randi has spent her career trying to do.
“I really love being able to help students and to be able to change the perception of math from something that’s scary or unattainable to something that’s accessible, something they understand, and something that can build confidence in them and their abilities.”
Randi’s own children watch her work. They see their mom writing curriculum, evaluating models, adopting families at Christmas. They see the whole loop of how work turns into impact, impact turns into a kid across town getting a present, or a student across the world getting a better explanation of long division.
“It’s very fulfilling to know that the work I’m doing on Outlier,” she says, “is helping my own children and students and teachers all over the world.”
Behind every advanced model is a person like Randi, someone who has spent years figuring out how to make a hard thing feel learnable, and who now brings that craft to the systems the next generation of students will learn from.
Step by step, until the hard thing becomes the next thing.
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