Brad Pitt's firm doesn't have a missing-tool problem. It has a tools-that-don't-talk problem, and a person sits between every pair of systems re-keying the same client data. Alejandro Castellano of Caddi joined me to unpack how AI agents can take over that back office work, and how to keep them on a short leash. If your team spends its week clicking between systems, this one's for you.
Map where your people re-key data between intake, matters, documents, signatures, and billing, because those hand-offs are where the time goes.
Look at back office automation before billable-work automation, since saving operational time puts money in your pocket without changing what you bill.
Constrain AI agents to the steps you've taught them, set permissions through IT, test before anything goes live, and require an audit log of every action.
Set firm-wide rules for agents, such as agents can draft client emails but never send them on their own.
Start with a low-risk experiment, like an agent that sorts your email into folders, and move off on-prem systems that limit what agents can do.
Alejandro Castellano is the CEO and co-founder of Caddi, an AI back office platform for law firms and other professional services firms. Born in Peru, he spent more than 10 years implementing technology in professional services, including real estate and financial services, before focusing on legal over the last three to four years. He studied electrical engineering in Peru, earned his master's at Cornell Tech in New York, and was accepted into the Allen Institute for AI Incubator in Seattle. He's the guest who comes to Brad Pitt's rescue in this episode's opening scenario.
Caddi: trycaddi.com
Red Cave Law Firm Consulting: redcavelegal.com
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law firm software integration, siloed systems, law firm automation, back office automation, AI agents for law firms, AI agents, legal AI tools, AI governance, law firm technology, legal tech, legal technology, practice management software, vibe coding, law firm operations, small law firm, solo practitioner, flat fee billing, Caddi, Jared Correia, Adventures in Legal Tech
[00:01:00 - 00:02:00] The vexing problem: intake, matters, documents, signatures, and billing live in separate tools, and people re-key data between them.
[00:03:00 - 00:04:00] Alejandro says roughly half of an expert's time, plus staff time, goes to clicking things around between systems.
[00:04:00 - 00:06:00] How Caddi works: a Discover agent finds automation opportunities, and Automate agents learn your process like a new employee.
[00:05:00 - 00:07:00] Time entries began as a way to measure capacity for everyone at the firm, and firms lost visibility into staff operations.
[00:06:00 - 00:08:00] Why automating the back office fits a law firm's business model better than automating the work you bill for.
[00:08:00 - 00:09:00] Flat fees and subscriptions: clients push prices down, yet distrust fixed pricing, and one attorney's subscription offer got a no from every client.
[00:09:00 - 00:11:00] Governance: agents constrained to the steps you teach them, plus oversight across departments and practice areas.
[00:14:00 - 00:16:00] Vibe coding horror stories: thousands of dollars burned on a job a $20 tool could do, and 2,000 records updated the wrong way.
[00:16:00 - 00:18:00] Permissions, workarounds, and testing before launch, plus a low-risk first experiment: sorting your email.
[00:26:00 - 00:29:00] No big clean-up needed first, the on-prem problem, and why Caddi now maps AI opportunities and ROI.
