Meet Caddi in personILTACONAug 23–27Future ProofSep 14–17

The Legal AI Landscape.

A thesis for your AI vendor portfolio strategy: the categories of legal AI and how they fit, mapped by ease of adoption against workflow breadth. Legal point solutions, AI assistants, IT-department automation, and AI development platforms each own a corner. Operations AI sits in the open square.

1-page PDFBuilt for COOs, CIOs, Firm Administrators & Directors of Innovation

One work email unlocks the PDF. No spam, unsubscribe anytime.

Build, buy, or teach the work.

The whole decision feels like a binary: buy a box or build it yourself. For operational work, both are bad. There is a third way most portfolios miss.

Buy a boxPoint solutions

Turn it on, no build. But it is fixed to one slice and one system, it will never match your firm's process, and you end up with one box per problem.

Build itPlatforms and coding agents

Fits anything your developers build. But it is a standing engineering project, it stalls at the firm-specific 20%, and the people who own the work cannot build it themselves.

Teach itCaddi

The person who owns the work demonstrates it once. It fits your exact process and runs itself, with no vendor box and no dev project. The option most portfolios miss.

Which square does a use case belong in?

Run each workflow in your portfolio through this. Most of them already have a home. The operational ones cluster in the last row, and that is the cluster worth a tool.

IfExpert legal judgment: research, drafting, contract analysis
A practice-of-law tool like Harvey or CoCounsel. Not Caddi.
IfOne-off or exploratory work
Horizontal AI like ChatGPT or Claude.
IfLives entirely inside one system, and the vendor ships a feature for it
That system's own AI.
IfCross-system, repeatable, operational, must run the same way every time and be auditable
Teach it to Caddi.

For the architect.

Where Caddi sits in the stack, and how it behaves in a regulated firm.

Deployment

Cloud, connected over OAuth and SSO. IT connects the firm's tools once in about five minutes; each user connects their own account.

Permissions

Runs under each user's own credentials, inheriting the access IT already set. No new permission model, no new secrets to manage.

Environment

Works with Citrix and on-prem stacks exposed through an Azure API. Nothing installed on the desktop; the recorder lives in Chrome.

Data

Middleware, not a data store. Caddi moves and processes information between your systems, it does not hold it.

Models

OpenAI, Anthropic, and Google, swapped per task. Zero data retention, abuse monitoring, and you can bring your own API keys.

Audit

Every API call and every action Caddi takes is logged across every system. Built for firms that get audited.

Caddi focuses on applying AI to real business workflows in ways that are useful and effective.

Jordan PortnerCOO, Portner & Shure