How one general counsel uses ChatGPT to juggle tasks

# General Learners

# ChatGPT

# Awareness

# Work

How Poshmark general counsel Adam Schlosser uses ChatGPT to spot legal issues, compare regulations across states, and turn dense rules into practical business guidance.

Adam Schlosser is general counsel at the online fashion marketplace Poshmark, and ChatGPT helps him juggle multiple tasks: first-pass researcher, legal-issue spotter, and interpreter of dense regulations into practical guidance for the business. But when Schlosser first got access to ChatGPT through an early enterprise rollout, the tool felt more like a novelty than a lawyer. Poshmark’s leadership wanted the company to explore AI to improve internal workflows around 2023 and 2024, and Schlosser was among the first internal users in that pilot. Early on, he found obvious holes, weak sourcing, and output that did not meet a legal standard. Then, in summer last year, something changed. Whether because the model improved, because it had learned his patterns, or because he built a private repository of key legal documents, ChatGPT began to understand Poshmark as a marketplace business and started answering in the frame he actually needed. By September 2025, it had become a tool he used daily, his first line of research. Schlosser says ChatGPT helps him cover tasks with a depth he otherwise would not have the time to do. He uses it first to flag issues and calibrate. When a new feature, product change, law, or headline appears, he asks how serious the issue is, which laws and regulations matter, how state rules differ, and comparisons for Canada. It is especially useful on established law and state-by-state comparisons, such as privacy rules where wording differences can change compliance obligations. He also uses it on the process side. He can dump everything he knows about an issue, then ask for a one pager for the CEO, a memo for leadership, or a chart for the CFO. He also uses it to vet outside advice, asking what consultants may have missed and what other questions he should be asking them. Schlosser gets the best results by treating ChatGPT like a junior associate who needs direction. He knows when to drill down, ask for exceptions, demand the actual regulation, and insist on exact wording. Sometimes he feeds in the full issue and asks ChatGPT to write the best prompt for itself, which he re-enters. But that only works because he brings his knowledge and experience. For Schlosser, practicing the law means reading its source code. Legal text is loaded with intentional choices where words like “shall” and “may,” as well as the difference between “and” and “or,” can change the level of obligation for companies. Long passages are packed with qualifiers, exceptions, and terms of art that look ordinary to a lay reader but carry different meanings for a lawyer. ChatGPT accelerates the search and synthesis of that text, especially on settled questions. Schlosser says lawyers still need to read the regulation itself, understand the exceptions, and make the judgment call.