Dennis Kozak, CEO of Ivanti, explains why endpoint management goes autonomous before customer-facing AI, why the patch apocalypse changes the math for every Fortune 500, and what makes buyers choose when seat-based licensing breaks under one-person-to-many-agents.

Dennis spent 22 years at CA Technologies through a company that ran 200+ acquisitions over 40 years, then drove 70% of Avaya's revenue as global channel chief. Three years ago he joined Ivanti as COO, became CEO on January 1, 2025, and now runs the platform 30,000 enterprises and 120 million users rely on for the operational backbone of IT and security. He is shipping autonomous IT operations across endpoints, ITSM, and security ops with two major 2026 product launches that
ship the thesis.


KEY INSIGHTS:
◼️ Why endpoint management goes autonomous before help desk or security ops (and what changes inside the IT department when it does)

◼️ How the 72-hour patch reverse-engineering window rewrites the math for every Fortune 500 patching cycle

◼️ What 30,000 enterprise customers actually look like when one Ivanti POC found 80% of devices missing significant patches and some had never been patched in years

◼️ Why the GSI managed services revenue stream consolidates fastest under autonomous IT, and which service lines get repriced


◼️ How AI native thinking differs from AI powered thinking inside Fortune 500 ITSM teams (the reframe most CIOs miss)

◼️ What variable-metric pricing replaces seat-based licensing when one person manages many agents and the help desk shrinks from 10 people to one with a good agent

TIMESTAMPS:

00:00 Teaser
01:30 Intro
01:44 Main Episode
02:46 The 22-Year Operator Arc: CA, Avaya, Ivanti
04:14 The Real Bet Behind “Embedding AI in Workflows”
05:54 Half a Billion Endpoints: What Most People Miss About Ivanti
07:04 Bridging IT and Security When Reporting Lines Won’t Bridge
14:18 Pick One: Where Autonomous Lands First Across ITSM, Endpoint, Security Ops
14:34 Why Endpoint Wins, And What Patch Tuesday Always Got Wrong
18:42 The Patch Apocalypse: Hours, Not Days, Not Weeks
20:55 The System of Record That Makes Three C-Levels Happy
21:46 The CIO and CISO Visibility Problem: You Can’t Patch What You Can’t See
24:52 Real Customer POC: 80% of Devices Missing Significant Patches
26:10 Why Some Airlines Can’t Fly Without Ivanti Software
27:12 Every Board Asks: What Is Our AI Story
30:52 AI Native Thinking vs AI Powered Thinking
34:18 Pricing Autonomous IT: Relative Value Beats Seats
38:53 Why Lovable’s Credit Model Found Power Users
42:57 What Happens to the GSI Managed Services Revenue Stream
46:28 The Horizon: What Excites a First-Time CEO Right Now


Follow Dennis Kozak: LinkedIn: kozakdennis
Follow Chirag Khanijau: LinkedIn: chirag-khanijau
Links: Ivanti: https://www.ivanti.com
Flywheelr: https://www.flywheelr.com
BrandStori: https://brandstori.ai
CXO Spotlight: LinkedIn: cxospotlight

Listen on Spotify: https://open.spotify.com/show/4xVy5IP... Listen on Apple: https://podcasts.apple.com/us/podcast...

#AutonomousIT #ITOperations #Ivanti #EndpointManagement #PatchManagement #ITSM #CIO
#CISO #EnterpriseSecurity #AgenticAI #PatchApocalypse #ITServices #ManagedServices
#FortuneFiveHundred #EnterpriseSoftware