Podcast: Automating CRE Accounts Payable Coding, with PredictAP CEO David Stifter

By Edward Cohen September 28, 2026 5:04 pm

Commercial Observer Tangent

David Stifter has spent more than two decades at the intersection of real estate, technology, and finance. As Managing Director and functional CTO at Digital Bridge (formerly Colony Capital), he led data architecture, process improvement, and finance transformation initiatives across major acquisitions. In 2020, he co-founded PredictAP with a team of B2B SaaS and AI veterans from Blizzard, Apple, and HubSpot. Since then, the company has grown to serve more than 130 real estate firms and process more than 7 million invoices a year. David is based in Lincoln, MA.

(02:20) From Colony Capital to founding PredictAP
(05:11) When a $60B firm couldn’t pay bills
(07:23) Why invoice coding is harder than it looks
(09:29) CAM pools, triple net leases, and the permutation problem
(13:43) When institutional knowledge walks out the door
(16:38) How to tell a real solution from a pretty demo
(20:48) PredictAP: From inbox to Yardi in 30 seconds
(24:47) Related Group, Cushman & Wakefield, and what 130 clients taught PredictAP
(27:59) Why integration makes or breaks AP automation
(30:17) Build vs. buy: what CFOs & COOs get wrong
(33:51) Sheriff vs. shepherd: how to manage AI adoption internally
(35:50) AP coding, audit risk, and financial misstatement
(38:44) Collaboration superpower: Richard Feynman