10 Acquisitions. 10 Legacy Systems. One Year to Transform and Deploy AI

10 Acquisitions. 10 Legacy Systems. One Year to Transform and Deploy AI

Muneer Hafez, CTO at Independence Pet Holdings, explains how to build a transformative AI platform while keeping legacy systems running, why most AI projects fail to deliver real dollars, and the radical choice to bifurcate yourorganization instead of asking people to choose between jobs and innovation.Muneer spent 30+ years in technology across Siemens, PwC, Deloitte, EY, and TransUnion, scaling everything from enterprise infrastructure to M&A integration at massive scale. At Independence Pet Holdings, he's managing one of the most complex transformations in enterprise today: modernizing 10 acquired companies with 10 different legacy systems, 10 different policy administration platforms, and 800,000+ insured pets, all while building an AI-native operation from scratch. The journey reveals why "stabilize first, then innovate" kills speed, how tribal knowledge becomes your competitive advantage, and what CIOs actually care about when vendors claim the same capabilities.Key Insights:■■ Why bifurcating your organization (legacy + AI-native running in parallel) is the fastest path to transformation, even though it costs more upfront.■■ How rebadging employees instead of laying them off solves three problems at once: tribal knowledge protection, team morale, and self-funding the new stack through cost savings.■■ Why 89% of AI projects deliver only blue money (soft benefits) instead of green money (dollars to the P&L), and what CIOs must demand from their teams.■■ The three fatal mistakes in every failed transformation: incremental culture change, shared resources that always prioritize the revenue engine, and copying old processes into fancy new tools.■■ How one-page strategy (vision without jargon) converts skeptical boards and tech teams, and why it beats 20-page presentations every time.■■ What IT professionals and developers should actually be learning now if they want to stay competitive as AI commoditizes coding.00:00 Introduction03:51 Career arc: from software engineer to CIO to business translator08:49 TransUnion's 50 data centers: the patterns that prepared him for this11:37 The sprawl revealed: 10 policy systems, hard-coded business logic, single points of failure14:39 800K+ pets insured but the systems are 15-20 years old18:49 Most people say "stabilize first, then AI." He chose both at once.20:33 The bifurcation strategy: two parallel organizations24:32 Why rebadging beats layoffs: tribal knowledge, morale, and self-funding26:34 Blue money vs. green money: why most AI projects don't move the needle31:42 The SAP lesson: conform yourself to the tool or it fails from day one35:04 People is always harder than technology36:45 Building culture from scratch: one-page strategy over 20-page presentations39:37 Self-funding through cost restructuring and managed services41:42 Risk mitigation: protecting the BAU while building the new42:01 One year in: what's working, what's still ahead46:53 Lemonade is the competitor. He wants to leapfrog them.48:07 The one-page strategy: for tech teams vs. business teams54:18 Partner selection for legacy vs. innovation: big fish in a small pond57:35 Why vendors driving strategy kills competitive advantage59:50 What developers and data scientists should focus on to future-proof careers01:04:01 Pet parent Miso: why he works with cats instead of dogs01:06:26 What excites him most about AI over the next two to three yearsFollow Muneer Hafez: https://www.linkedin.com/in/munirhafezFollow Chirag Khanijau: https://www.linkedin.com/in/chirag-khanijauLinks:Independence Pet Holdings: https://www.independencepetholdings.comFlywheelr: https://www.flywheelr.comBrandStori: https://brandstori.aiCXO Spotlight: https://www.linkedin.com/showcase/cxospotlightListen on Spotify: https://open.spotify.com/show/4xVy5IPCvf68BrGaALfUMZListen on Apple:https://podcasts.apple.com/us/podcast/cxo-spotlight-growth-influence-leadership-in-b2b/id1792963542

This CIO is Making Her Entire Enterprise AI-Ready | 29M Students, Cambium Learning Group

Dr. Diana Cano, Chief Information Officer at Cambium Learning Group, explains why AI readiness fails when it starts with technology instead of business strategy, how education can use AI responsibly at the scale of 29 million students and 3 million teachers, and what CIOs actually need from partners when every vendor claims to be AI-powered.Diana has moved across five industries, from GE and Honeywell to ETS, Odyssey, and now Cambium Learning Group, bringing a repeatable pattern of leading change through complex technology environments. Two years ago, she joined Cambium Learning Group, an education technology company serving millions of students and teachers, to help scale technology, AI adoption, and responsible innovation in a market where every decision can directly affect learning outcomes.◼️ Why AI readiness fails when it becomes an IT initiative instead of part of the business strategy◼️ How CIOs can move teams from AI curiosity to confidence through low-risk, practical experimentation◼️ What partners must prove before their AI solution is trusted in a real enterprise environment◼️ Why shadow IT can become a feedback loop for CIOs instead of just a governance problem◼️ How mission-driven companies compete for AI talent when they cannot match Big Tech salaries◼️ Why education’s slower AI adoption is not hesitation, but purposeful responsibility00:00 Teaser: AI Readiness, Shadow IT, and Vendor Claims01:18 Introduction02:37 What Five Industries Taught Diana About Change04:57 Applying Physics to Leadership and Management07:50 Building AI Readiness for 29M Students08:36 Why AI Adoption Starts With Relatability13:29 Explaining AI Value to Business Leaders17:34 The AI Hurdle CIOs Don’t Talk About Enough19:10 Why CIOs Need Learning Tours, Not Listening Tours23:26 Why Every Employee Is Becoming a Technologist24:00 Why Shadow IT Is a CIO Feedback Loop25:00 How CIOs Can Self-Fund AI Initiatives29:42 Competing for AI Talent With Mission32:58 How CIOs Should Evaluate AI Partners34:24 The Three Proofs Every AI Vendor Must Pass39:14 Why AI Will Change Tech Pricing Models43:31 AI Use Cases That Delivered Real Value49:23 What Responsible AI Looks Like in Education54:35 Why AI Can Personalize Learning at ScaleFollow Diana Cano: https://www.linkedin.com/in/dianacanoFollow Chirag Khanijau: https://www.linkedin.com/in/chirag-khanijauLINKS:Cambium Learning Group: https://www.cambiumlearning.comFlywheelr: https://www.flywheelr.comBrandStori: https://brandstori.aiCXO Spotlight: https://www.linkedin.com/showcase/cxospotlightListen on Spotify: https://open.spotify.com/show/4xVy5IPCvf68BrGaALfUMZListen on Apple:https://podcasts.apple.com/us/podcast/cxo-spotlight-growth-influence-leadership-in-b2b/id1792963542#CXOSpotlight #DianaCano #CambiumLearningGroup #CIO #ChiefInformationOfficer #AIReadiness #EnterpriseAI #AIAdoption #ResponsibleAI #EdTech #EducationTechnology #DigitalTransformation #TechnologyLeadership #ITLeadership #AIGovernance #FutureOfEducationSubscribe to CXO Spotlight for more conversations with technology leaders shaping the future of enterprise AI, digital transformation, and business leadership.

A Top 10 CISO on How to Actually Sell to a CISO (and What Vendors Keep Getting Wrong)

Mignona Coté, a top 10 CISO in the world with three decades of security leadership across AWS, PepsiCo, Bank of America, and Infor, reveals what vendors keep getting wrong in the first meeting, why every cloud platform is equally secure, and how the "human in the loop" governance model breaks the moment AI touches your stack.Mignona has led security through three major technology inflection points: the explosive growth of the internet at GTE and Verizon, the financial crisis at Bank of America where she ran security for 200,000 people across credit cards, home loans and Merrill Lynch, and the cloud adoption wave at AWS. Most recently as SVP and CISO at Infor, she was responsible for the security of a platform serving more than 60,000 companies across industries. She is a top 10 CISO globally, a two-time Dallas ORBIE Award winner, and a Hall ofFame inductee who today advises a portfolio of security startups.◼ Why every cloud platform is equally secure, and the real question CIOs should be asking instead◼ How AI has broken the traditional "human in the loop" model and what has to replace it◼ What vendors must do in the first meeting to win a CISO's trust (hint: bring two people, not fifteen)◼ Why CISOs who stay in one role too long start solving yesterday'sproblems◼ The empathy framework that turns developers into security allies instead of compliance checkboxes◼ What CISOs talk about privately that never makes it into theboardroom00:00 Teaser00:53 Intro01:07 Main Episode01:53 Three decades in, top 10 CISO globally, still learning from 5am to 7am02:47 What it means to be the security officer for 60,000 companies03:46 From the dot com era to the financial crisis to the cloud04:14 Why each company forces a completely different security program05:29 What banking, telecom, and consumer tech each taught her07:26 Leaving the single-company CISO role for advisory work08:15 What builders of enterprise AI platforms keep getting wrong10:37 The “default secured” principle every product team should adopt13:11 88% human error, 63% inadvertent sharing: where SaaS responsibility sits14:39 Empathy as a security strategy, and why auditors get it right17:32 “Shift left, shift left. I call it shift anywhere.”17:37 How AI compounds the threat and breaks old governance models19:07 Building a governance model that flexes like Lego21:28 What feels different about this AI inflection point22:16 Inside the CISO Ascent Board: what CISOs never tell the board26:07 The advice she would give early-career security professionals26:53 Why staying in one role too long will hurt you28:25 Why CISOs have to get hands on with the technology29:46 What single-cloud security misses about multi-cloud reality31:35 The questions CIOs should ask vendors, but rarely do33:39 Choosing the right partner: accessibility over sales pitch34:27 The CrowdStrike account rep story every vendor should hear35:12 What IT services companies must change to sell to CISOs36:34 Chirag’s keynote reframe: “Nobody wakes up saying let me see a demo today”37:20 The late-night call, the board presentation, and digital watermarking38:28 What excites her about the startup security space40:29 What AI will change about the CISO role in two years41:07 The one question the host forgot to askFollow Mignona Coté: https://www.linkedin.com/in/mignonacoteFollow Chirag Khanijau: https://www.linkedin.com/in/chirag-khanijauLinks: Flywheelr: https://www.flywheelr.comBrandStori: https://brandstori.aiCXO Spotlight: https://www.linkedin.com/showcase/cxospotlightListen on Spotify: https://open.spotify.com/show/4xVy5IPCvf68BrGaALfUMZListen on Apple:https://podcasts.apple.com/us/podcast/cxo-spotlight-growth-influence-leadership-in-b2b/id1792963542#CXOSpotlight #CISO #Cybersecurity #CloudSecurity #MultiCloud #InformationSecurity #SaaSSecurity #AISecurity #SecurityGovernance #EnterpriseIT #CIO #CISOCommunity#VendorSelection #ITServices

An AI Just Out-Hacked 2 Million Humans. She Decides What Happens Next | Nidhi Aggarwal, CPO HackerOne

Nidhi Aggarwal, Chief Product Officer at HackerOne, explains why the zero-day clock dropped from 23.2 days to 20 hours in a single year, why the entire CISO playbook is being rewritten around continuous defense, and what she is hearing from the CISOs at 20% of the Fortune 500 who are losing sleep over Mythos and autonomous AI hackers.Nidhi is one of the most uniquely qualified people to answer these questions. She co-founded a cloud platform that Google acquired. She holds six US patents. She has built products at McKinsey, HP Labs, and VMware. She now steers the AI roadmap at the platform that pays out $81 million a year to ethical hackers, manages over 2 million security researchers, and just watched an autonomous AI climb to number one on their own leaderboard. Her customer list is the companies that would be on the front page of the Wall Street Journal if they were breached.KEY INSIGHTS:◼ Why the entire security architecture was built on an assumption that is no longer true, and what CISOs should do with the boardroom attention Mythos just bought them.◼ How the zero-day clock compressed from 23.2 days to 20 hours in 12 months, and why that single metric reframes the entire CISO operating model.◼ Why "vulnerability ops" is the DevOps moment for security, and what a continuous detection pipeline actually looks like in practice.◼ The Mozilla case that changed her mind on AI slop: 122 vulnerabilities found, 14 high and critical, zero that represented true exposure. Why defense is offense.◼ Why the ethical researcher community is adopting AI faster than CISOs and why that is the single biggest silver lining in this moment.◼ The HackerOne platform data nobody else has: 300% increase in open source vulnerability reports from January to March, duplicate rates jumping from 22% to 47%, and what the high and critical findings actually tell us.TIMESTAMPS:00:00 Introduction01:17 An atypical path from HP Labs to McKinsey to Google acquisition to HackerOne05:19 What HackerOne is today, not what you think it is08:06 The Wall Street Journal customer list10:07 Mythos and the moment CISOs spent the night editing their war plan11:04 The zero-day clock, 23.2 days to 20 hours13:01 How CISOs should proactively prepare right now14:42 Humans, agents, and AI together on the leaderboard17:28 How to propose the new cybersecurity posture to the board18:10 The full continuous defense playbook20:04 Vulnerability ops, the DevOps moment for security21:04 Bug class elimination instead of whack-a-mole23:22 Mozilla, 122 vulnerabilities, and the power of defense23:29 Defense is offense25:53 The new cybersecurity team, aligned with business speed28:42 Patterns from CISO conversations right now29:02 Platform data, 76% volume increase tied to Opus 4.630:10 300% increase in open source reports, duplicate rates, high and critical findings32:15 The AI creating the problems is the solution35:09 The CISO nirvana state, a self-healing security layer36:40 Diversity of thought as a security capability39:30 Why this future is more possible than it sounds40:24 Advice to the ethical researcher and cybersecurity communityFollow: Nidhi Aggarwal: https://www.linkedin.com/in/nidhi-aggarwal-6454ab1/Follow: Chirag Khanijau: https://www.linkedin.com/in/chirag-khanijauLinks: HackerOne: https://www.hackerone.com/ Flywheelr: https://www.flywheelr.comBrandStori: https://brandstori.aiCXO Spotlight: https://www.linkedin.com/showcase/cxospotlightListen on Spotify: https://open.spotify.com/show/4xVy5IPCvf68BrGaALfUMZListen on Apple: https://podcasts.apple.com/us/podcast/cxo-spotlight-growth-influence-leadership-in-b2b/id1792963542#CyberSecurity #CISO #HackerOne #AIsecurity #AgenticAI #BugBounty #VulnerabilityManagement #ZeroDay #EthicalHacking #SecurityLeadership #AISecurity #CTEM #AppSec #AIRedTeaming #PromptInjection

Why Strategy Is the New Operating System - C1's CSO on the Bold Moves That Matter

Why Strategy Is the New Operating System - C1's CSO on the Bold Moves That Matter. Candace Holt, Chief Strategy Officer at C1, explains why strategy is the framework for execution, how organization actually prioritize when everything seems urgent, and what buying decisions look like from inside the C-suite.C1 serves nearly half the Fortune 500. Candace doesn't just own strategy. She owns marketing too, and she's executing it. Before C1, she spent eight years at Accenture running business operations and global alliances, watching transformation from the consulting side. Now she's building it. Her pattern: bring clarity through discovery, build alignment through participation, then operate with intent. No PowerPoints. No planning. Operating.Key Insights■■ Why Strategy Is Not Strategy Until It ExecutesStrategy isn't an ethereal function. Real strategy brings clarity that flows through go-to-market, sales enablement, and decision-making across the company. It's 80% science, 20% art.■■ How to Stop Planning and Start OperatingMost CSOs plan. Candace operates. Planning writes the roadmap and hopes it sticks. Operating means using insights to make choices that actually change trajectory. The difference determines whether your business adapts or stalls.■■ Before Buying Any Tool, Fix Your Processes FirstEvery organization wants to bolt AI everywhere. But if your processes are broken, you're automating broken things. Discovery, hypothesis, feedback, execution. In that order. Tools amplify what you already have.■■ Customer Concentration as Strategic AdvantageCandace discovered that a tiny percentage of C1's customers drove disproportionate revenue. Instead of spreading thin across everyone, she wrapped strategic programs around those high-value customers and the executives supporting them. It changed the entire business posture.■■ The Framework That Turns Clarity Into Competitive AdvantageDiscovery of market and internal friction, hypothesis as strategic bets, feedback that brings teams along, execution with aligned leadership. This discovery-hypothesis-feedback-execution cycle is how strategy scales across AI implementation, go-to-market, and organizational alignment.■■ What's Coming Next in AI-Driven StrategyThe next three years will test which organizations have real strategy and which bolted AI on as a tactic. Candace is betting that the companies with clear strategy frameworks, disciplined customer focus, and aligned leadership will win. Everything else is noise.Follow Candace Holt: https://www.linkedin.com/in/candaceholtFollow Chirag Khanijau: https://www.linkedin.com/in/chirag-khanijauLinks:C1: https://www.c1.comFlywheelr: https://www.flywheelr.comBrandStori: https://brandstori.aiCXO Spotlight: https://www.linkedin.com/showcase/cxospotlightListen on n on Apple:https://podcasts.apple.com/us/podcast/cxo-spotlight-growth-influence-leadership-in-b2b/id1792963542#CSO #ChiefStrategyOfficer #StrategyExecution #OperatingSystem #AIStrategy #B2BLeadership #ExecutionFramework#OrganizationalAlignment #CXOSpotlight #StrategicLeadership #GoToMarket #ProcessBeforeTools #CustomerFocus#EnterpriseLeadership #TransformationLeadership