Keeper is an AI tax platform for complex returns, with a focus on serving solo business owners and freelancers in the U.S.
Interest in solopreneurship has exploded over the past few years, in no small part aided by the advent of AI. Every one of these new businesses needs help with taxes.
Today, the tools are scattered. Many solos do nothing at all until tax time, when they scramble to file in Turbotax and end up drastically under-claiming deductions. Others cobble together Quickbooks for their expenses, Gusto for 1099 forms, and a CPA for handling tax returns. It’s a lot to keep track of, and it sucks. Keeper handles all of this work in a seamless, AI-native platform.
Keeper serves over 40,000 paying customers and generates over 8 figures of annualized revenue.
Given our core business, Keeper is uniquely positioned to contribute to the public discourse happening at the intersection of AI and solopreneurship.
To tap into this moment, we're building a public AI benchmark that measures how well frontier models (ChatGPT, Claude, Gemini, etc.) can do real-world self-employment tasks: creating marketing materials, organizing a work portfolio, categorizing a year of expenses, reviewing a client contract, etc.
Think GDPval (OpenAI's benchmark for professional work), but for the tens of millions of Americans who work for themselves. At the end of the project, we'll publish the results, the methodology, and a leaderboard.
As the Research Operations Intern, you’ll co-lead the task compilation portion of this project with the CEO. This is a dynamic role where daily responsibilities will shift dramatically over the course of the internship. At the onset, you’ll work with Keeper’s freelancer customers to design the workflow for the first set of tasks. You’ll study the literature and other benchmarks to assess questions like:
Examples of projects you’ll own
Discovery interviews:
Task recruitment:
Synthetic input creation: