How Covenant Legal got ahead of ChatGPT

"Deployed to our VPC in a week. Audit logs worked on day one."
Marcus Holt
Chief Information Officer, Covenant Legal
Company
Covenant Legal
Industry
Legal
Based in
Chicago
Founded
1994

Covenant Legal is a 400-attorney firm specializing in M&A, tax, and regulatory practice. Like every law firm in 2025, they had a ChatGPT problem: associates were already pasting client documents into consumer LLMs to summarize them. The firm needed a sanctioned alternative before something went wrong.

The shadow AI problem

Marcus Holt had been warned about shadow AI for a year. A quick survey of associates turned up what everyone suspected: over 60% admitted to using ChatGPT for work at least occasionally, and a smaller number were pasting client-sensitive documents without realizing the implications.

Covenant's risk committee gave Marcus a deadline: ship a firm-sanctioned alternative in 90 days, or they'd block external LLM access at the firewall.

"We couldn't block our way out of this. Attorneys would just use their personal laptops. We needed a tool that was better than the rogue option."

Marcus Holt, Chief Information Officer

On-premise, fast

Covenant's IT policy requires all AI tools to run inside their AWS VPC with no external API calls. Most RAG tools on the market either required cloud APIs or had a self-hosted option that felt like an afterthought.

Embedix was built for VPC deployment from the start. The initial installation took four days. Full deployment to all 400 attorneys took three weeks.

The first audit went smoothly

Three months after deployment, Covenant's malpractice insurer asked for an audit of AI usage. The team exported a full retrieval log from Embedix in under an hour: every query, every document retrieved, every attorney, every client matter.

The insurer approved the program and lowered Covenant's cyber premium.