

AI in the Deal Room
Private Dinner Chicago | AM&AA Summer Conference
This dinner is part of an ongoing series that has already convened TAS practice leaders from more than 50 CPA firms across multiple cities. The Chicago edition continues that conversation. It's a closed-door exchange of what's actually working (and what isn't) on live engagements, grounded in real processes rather than theory.
AI is starting to change how deal advisory work gets done, but not evenly.
While large firms are investing heavily into AI, many transaction advisory teams, especially in the mid-market, are still operating with workflows that haven't fundamentally changed in years. At the same time, early shifts are beginning to appear in how parts of M&A and diligence are executed, quietly compressing timelines and changing where value sits in the process.
The result is a growing gap in speed, cost structure, and ultimately in how firms compete for and deliver work.
A small group of practitioners across transaction advisory, private equity, and M&A will join for a candid, off-the-record discussion.
On the table:
What happens to junior professionals when AI automates the work they were hired to do, and how do firms rebuild the talent pipeline?
How does the transaction advisory service model itself need to evolve alongside AI in scope, pricing, and delivery?
Where is value shifting in M&A and diligence, and who captures it as timelines compress?
What are the early movers doing differently, and what should mid-market firms borrow now?
Seats are limited. By invitation only.
Hosted by Dobs.ai - an AI platform focused on automating document-heavy workflows in transaction advisory, including QoE and diligence processes.