CXO Spotlight: Growth, Influence & Leadership in B2B

About CXO Spotlight: Growth, Influence & Leadership in B2B

CXO Spotlight by Flywheelr is a conversation series with world's top enterprise technology CXOs. These CIOs, CTOs, CDOs are at the absolute frontier of technology and AI at truly enterprise scale. We ask the hardest questions on how to make it work so it unlocks the solution for millions of other business leaders. 200+ conversations with the C-suite across financial services, healthcare, manufacturing, and technology. No vendor pitches. No panel-speak. The conversations technology leaders have with each other when the analysts aren't in the room.

Publisher

CXO Spotlight

Category

technology

Language

en

Explicit

No

First episode

27 Jan 2025

Latest episode

5 Nov 2026

Latest episodes

35 episodes in the feed.

1. 

   5 Nov 2026

   90% of Ransomware Starts Here: The Identity Security Problem CISOs Underestimate | Alex Weinert, CPO Semperis

   Alex Weinert, Chief Product Officer at Semperis, explains why 99% of permissions granted inside enterprises are never used, why agentic AI turns that dormant attack surface into "fireworks," and what CIOs actually need to tell their boards before the next ransomware event takes identity offline. Alex spent 30 years at Microsoft, started the identity security team in 2012, and led the response to some of the largest nation-state identity attacks in history including SolarWinds, Storm-0558, and Midnight Blizzard. His blog post "Your Pa$$word Doesn't Matter" is one of the most-cited pieces in identity security. Now at Semperis, he is building the identity resilience category, protecting over 100 million identities across Active Directory, Entra, Okta, and Ping in a market where over 80% of breaches start with compromised identity. ◼ Why 99% of permissions granted in most enterprises are never used, and why that dormant surface becomes catastrophic the moment agents show up ◼ How the mental model of an AI agent as a "hyper intelligent, hyper active, sociopathic five year old" changes every identity security decision ◼ What actually happened when customers tried to run incident response while the attacker was sitting on the Teams call and reading their response playbook ◼ Why the first thing every CISO should do Monday morning has nothing to do with new tools and everything to do with mothballing abandoned applications ◼ How to explain identity resilience to a board in one question: what happens if nobody in your company can log in for four weeks ◼ Why identity resilience is one circuit, not three products: posture, detection, and recovery have to spin as a single wheel 00:00 Teaser 01:23 Intro 01:36 Main Episode 02:20 30 Years Protecting 20 Billion Sign-Ins a Day 06:42 Why Your Password Doesn't Matter 12:09 Why Alex Left Microsoft for Semperis 16:56 The Shift from Account Attacks to Infrastructure Attacks 18:48 Why Identity Is Still an Afterthought for Most CISOs 22:57 The 99% Permissions Problem That Breaks Everything 24:07 How Microsoft Killed 780,000 Applications in Two Weeks 26:51 The Sociopathic Five Year Old: How to Think About Agents 27:30 Why Agentic AI Changes Identity Security Forever 32:02 Expanding Beyond Active Directory: The Fabric View 35:39 Real Ransomware Stories: Card Keys, Teams Calls, and Locked Buildings 37:50 How Ready Are Most CISOs Actually 38:55 Treating Security Teams Like High Performance Athletes 40:24 The Three Beliefs Behind Identity Resilience as a Category 43:15 What Every CISO Should Do Monday Morning 45:09 How to Explain Identity Resilience to Your Board 48:33 What the Data Across 100 Million Identities Is Telling Semperis 49:59 Advice to the Next Generation of Security Leaders 54:30 What Alex Is Most Excited About in the Next Two Years Follow Alex Weinert: https://www.linkedin.com/in/alexweinert Follow Chirag Khanijau: https://www.linkedin.com/in/chirag-khanijau Links: Semperis: https://www.semperis.com BrandStori: https://brandstori.ai CXO Spotlight: https://www.thecxospotlight.com CXO Spotlight on LinkedIn: https://www.linkedin.com/company/cxospotlight Listen on Spotify: https://open.spotify.com/show/4xVy5IPCvf68BrGaALfUMZ Listen on Apple: https://podcasts.apple.com/us/podcast/cxo-spotlight-growth-influence-leadership-in-b2b/id1792963542 #CXOSpotlight #IdentitySecurity #CISO #Cybersecurity #ActiveDirectory #IdentityResilience #Semperis #AgenticAI #Ransomware #ZeroTrust #EntraID #IAM #CyberResilience #BoardRisk #EnterpriseSecurity

2. 

   23 Oct 2026

   When AI Can Fake Anything, How Do You Sell Trust?

   Karen Kaukol, CMO at Entrust, explains how to market trust and identity security when both the threat (deepfakes, AI fraud) and the defense are powered by AI. Karen spent 17 years at First Data managing digital marketing through an IPO and portfolio transformation, then joinedEntrust nearly a decade ago as CMO to lead marketing strategy for a global digital identity and security leader protecting the world's most critical transactions across 150 countries.Key Insights:■■ Why candor beats hype when marketing security. Enterprise buyers are tired of fear-mongering and AI buzzwords. They respect vendors who shoot straight about what's working, what's uncertain, and where the real risks live.■■ The paradox: defending against AI-powered attacks while using AI to market that defense. Both threaten and protect at scale. The key is transparency about how you're using AI and honest acknowledgment of what you don't yet know.■■ Buying committees have exploded to 14-17 cross-functional people who tune out jargon. You must always reframe back to the business problem you're solving, not the technical terminology.■■ Brand awareness is a revenue lever, not a cost center. Most marketers can't prove the connection. Karen shows how to build a funnel from awareness to preference to consideration to revenue, then prove it with real customer data to your board.■■ AI-enabled video production costs one fifth of traditional agencies ($100K vs $500K) and delivers 60% faster with better iteration cycles. In-house creative plus boutique agency plus AI tools creates multiplying effect.■■ The real differentiator is trust, built through learning communities, thought leadership, and third-party validation. Owning the conversation before the sales funnel means your brand becomes the discovery engine.Timestamps:00:01 Introduction01:03 Karen's 30-year career arc through product, marketing, and innovation02:53 What Entrust does: securing identity across the full lifecycle04:21 Scale of Entrust's reach: every credit card, corporate login, banking transaction05:20 Karen's CMO scope: product, brand, performance, communications06:39 How Entrust uses AI as core to marketing workflows07:52 The brand campaign that cost one fifth the traditional budget08:58 Buyers using AI to research before ever visiting your website10:35 The paradox: defending against AI while using AI to market12:46 Enterprise buyers are tired of hype and fear-mongering14:59 Why candor and transparency win over bold promises15:57 The jargon tax problem: explaining post-quantum cryptography to non-technical buyers17:58 Reframing security concepts to business outcomes not technical specs19:25 Three phases of buyer journey: awareness, trust, conversion22:37 What activities belong in each phase with real examples25:36 Building the Identity Thread: owned community as competitive advantage26:57 Quality over volume in content strategy for sophisticated buyers27:16 Moving beyond vanity metrics to actual revenue impact KPIs30:51 How to prove brand impact to board with funnel data33:48 Zero-based budgeting: reject inertia, allocate based on business case36:48 Portfolio A-book/B-book analysis forces focus over spray-and-pray40:05 What's increasing: website optimization for AI, selective in-person events42:28 What's decreasing: volume of content, commoditized brand campaigns43:20 Behind the scenes: AI video production under 100K in 60% less time47:32 What marketing skills matter most in AI era: critical thinking, judgment, curation49:30 What excites Karen about next three years of security automationlFollow Chirag Khanijau: https://www.linkedin.com/in/chirag-khanijau #TrustMarketing #AI #CybersecurityMarketing #IdentitySecurity #B2BMarketing #EnterpriseMarketing#ContentMarketing #BrandBuilding #MarketingLeadership #BuyerJourney #ThoughtLeadership #DigitalTransformation

3. 

   28 Sept 2026

   Autonomous IT Operations: Why the Boring Half of IT Goes Autonomous First | Dennis Kozak, CEO Ivanti

   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 thatship 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: https://www.linkedin.com/in/kozakdennis/ Follow Chirag Khanijau: https://www.linkedin.com/in/chirag-khanijau Links: Ivanti: https://www.ivanti.com Flywheelr: https://www.flywheelr.com BrandStori: https://brandstori.ai CXO Spotlight: https://www.linkedin.com/showcase/cxospotlight Listen on Spotify: https://open.spotify.com/show/4xVy5IPCvf68BrGaALfUMZ Listen on Apple: https://podcasts.apple.com/us/podcast/cxo-spotlight-growth-influence-leadership-in b2b/id1792963542 #AutonomousIT #ITOperations #Ivanti #EndpointManagement #PatchManagement #ITSM #CIO#CISO #EnterpriseSecurity #AgenticAI #PatchApocalypse #ITServices #ManagedServices#FortuneFiveHundred #EnterpriseSoftware

Who has been a guest on CXO Spotlight: Growth, Influence & Leadership in B2B

Names identified in recent episode analyses. Showing up to five guests.

• Ram Tyagi
• Bill Blount
• Gary Sidhu
• Shuchi Agrawal
• Vishal Shukla

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

178,202

Score snapshot 15 Sept 2025

Apple Podcasts (US)

5.0 / 5

1 ratings

Spotify

5.0 / 5

1 ratings

Podcast Authority Score: 54 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

59

Social presence

0

YouTube

93

Engagement

32