Cloud Sprawl Is a Procurement Problem: Fix It Before Your Next Renewal | Matt LeBaron

Two companies can buy the same Microsoft license. One pays $20 a seat, the other pays $10, and neither one knows what the other pays. Matt LeBaron has saved clients more than $1 billion on cloud, software and AI by seeing across those prices. One Fortune 500 client had 42 vendors doing the same job. Others are getting VMware renewal quotes from Broadcom just months before the deadline, on a platform that takes a year or more to migrate off. In this fireside chat that opened Day 2 of the Cloud Convergence Summit, Fernando Labastida talks with Matt, founder and CEO of Pocketbook, about where cloud and software money leaks out. His answer starts well before the renewal date. By the time a vendor knows you can't switch in time, you have almost no leverage left. What you'll learn: • What a third party sees in your cloud and software spend that you can't • Why more volume makes it harder to know if you're getting a good deal • From 42 vendors to 20, and why the sweet spot is two to four • Champion-challenger vs. dual vendor models, with an 80/20 AWS and Google Cloud example • The VMware lesson: why exit planning has to start years ahead • Non-commercial terms that matter as much as price: price protection, data protection and indemnification • What to watch for with AI vendors, and what may happen to AI pricing when venture money tightens • Why contract lengths are shrinking from three years to one or two • Your 90-day renewal checklist, and the notice clause that can lock you in before you start • Will AI replace software applications? • Q&A with Jimmy Jobe: "IT arbitrage" and moving workloads to the best-fit cloud • Why non-public data has never been more valuable • New AI agent accountability rules in insurance About the speaker: Matt LeBaron is founder and CEO of Pocketbook, which helps engineering and finance teams find waste, optimize vendor contracts and govern tech spend. He has saved clients more than $1 billion on cloud, software, AI and infrastructure. He holds an MBA and a master's in computer science from Wharton and was a Tech Strategy Director at PwC. About the summit: The Cloud Convergence Summit ran online October 8–9, 2026, hosted by Verge Technologies with Carahsoft. Two afternoons of sessions on managing many clouds as one. Day 1 covered infrastructure and architecture. Day 2 covered governing what the machines decide. ⏱️ CHAPTERS 0:00 Introduction 1:20 What a third party sees that you don't 3:30 Applying it to cloud 4:50 Four to seven clouds and losing control 5:45 42 vendors doing the same thing 6:50 Why fewer vendors cost less 8:00 The risk of locking in to one vendor 11:00 Champion-challenger and dual vendor models 12:15 What if two outages hit at once? 13:00 VMware and planning your exit years ahead 15:00 What to plan for in the next three to five years 15:50 Non-commercial terms and price protection 18:10 Data protection and indemnification 19:30 What to watch for with AI vendors 21:00 Jimmy Jobe on IT arbitrage 26:00 Data as an asset, and why non-public data is worth more 31:00 Why contracts are getting shorter 33:00 90 days out from a renewal 37:00 Will AI replace software applications? 39:30 How AI is shaping cloud decisions 42:20 Q&A: consolidate or diversify? 45:40 Resellers and leverage 46:50 AI agent rules in insurance 🔗 Pocketbook: https://pocketbk.com 🔗 Learn about Verge Technologies and SentientDB: https://vergetech.cloud 🔗 See the full summit lineup: https://summit.vergetech.cloud #CloudCosts #FinOps #CloudSprawl #VendorManagement #SaaS #Procurement #CloudConvergence #CFO