The CTO Compass

Mark Wormgoor

The CTO Compass is a podcast about CTO, CIO, and tech leadership - on strategy, scaling, teams & bringing clarity to technology leadership for real boardroom impact. Hosted by Mark Wormgoor, each episode features candid conversations with experienced CTOs, CIOs, and senior tech leaders from startups through to large enterprises. The focus is on the real work of leading in tech: – Setting clear tech strategy that aligns with business goals – Scaling teams and culture – Making high-stakes decisions under pressure – Navigating the transition from hands-on engineer to executive leader This is not a hype show, nor a theoretical leadership podcast. Guests share hard-won lessons, mistakes, and practical insights from the moments that mattered most - when clarity was missing, heavy decisions needed to be made, and leadership was tested. If you’re a CTO, CIO, or tech leader looking to sharpen your thinking, increase your influence, and create real impact in the boardroom, The CTO Compass is built for you.

  1. Why Organizational Change Fails: The Hidden Politics and Self-Interest Killing Your Transformation ft. Bud Caddell

    6D AGO

    Why Organizational Change Fails: The Hidden Politics and Self-Interest Killing Your Transformation ft. Bud Caddell

    Mark Wormgoor sits down with Bud Caddell, founder of NOBL, to explore the human friction that often stalls massive technology initiatives. Bud shares his transition from a software developer to a change management expert, triggered by witnessing "shiny" innovation projects collapse under the weight of organizational politics and conflicting incentives. The conversation dives deep into why many digital transformations are dead on arrival, often due to manufactured urgency and a lack of focus that spreads leadership teams too thin. The discussion shifts toward practical strategies for overcoming these barriers, with Bud advocating for a "piecemeal" approach to organizational change. Rather than following a rigid, 200-slide consultant deck, he suggests using "safe to fail" experiments to surface hidden politics and resistance early in the process. They also tackle the evolving role of the CTO in the age of AI, discussing how tech leaders are gaining unprecedented power but risking their internal relationships by failing to build empathy with the teams impacted by these rapid shifts. Finally, Bud addresses the growing issue of organizational cynicism and the "trust gap" between leaders and employees. He argues that the antidote to mass change fatigue isn't better technology, but radical honesty and transparency regarding what an organization can and cannot control. The episode concludes with a look at how leaders can build resilience by moving away from purely visionary "Steve Jobs" personas toward a more grounded, transactional, and honest theory of leadership. Key Takeaways • Many projects fail not because of the tech, but because "manufactured urgency" exhausts the organization’s attention span before the change can take root. • Avoid "rip the band-aid off" transitions; instead, use small, iterative experiments to discover where political resistance and sabotage actually live. • Apply agile experimentation to cultural rituals and habits, but use traditional stakeholder mapping and steering committees for high-risk reorgs or core system implementations. • Recognize that most "sabotage" is actually people protecting their teams or resources; breaking through requires negotiating power and resources rather than just fighting for a meritocracy. • As AI pushes more power toward the CTO, be careful not to burn bridges with other executives; success depends on building a coalition, not just wielding technical influence. • To reduce change fatigue, stop over-promising; be transparent with employees about layoffs, market pressures, and the specific limitations of your control. About BudBud Caddell is the Founder and CEO of NOBL, a global transformation consultancy reshaping how organizations adapt to change. Since 2014, he has led more than 120 engagements across five continents, helping companies in more than 20 industries, including Nike, Ford, CNN, and HBO, navigate disruption, repair dysfunctional cultures, and build resilient teams. Recognized by The Guardian as one of the “strategists to watch” and named one of Business Insider’s “most creative people under 30,” Bud’s work has been featured in The New York Times, The Wall Street Journal, Forbes, and AdAge. Before launching NOBL, he was a Partner at Undercurrent and served as SVP of Digital Strategy and Innovation at Deutsch LA. Bud Caddell is a distinguished speaker and guest, having delivered keynote addresses at SXSW, TEDx, and the Reuters Strategic Marketing Conference. His core message emphasizes that organizational failures rarely result from a lack of ideas. Instead, they stem from cultural, political, and psychological barriers that prevent those ideas from succeeding. He is available to provide expert commentary on leadership and organizational change, including how executives can sustain trust and momentum during crises, why workplace cultures often falter in execution, and how to foster environments where innovation thrives. He also addresses the evolving expectations of employees in the future of work, explains why the majority of brand and business transformations fail, and offers strategies to design change that lasts. Chapters00:00 Getting Into Change Management 07:26 What Kills Great Ideas? 14:05 Aligning Individual Self-Interests 17:25 Ad 17:56 The Reality of Reorganization 27:35 Unexpected Transformation 31:02 Looking for Change! 34:50 Ad 35:00 Team Capacity vs Company Demand 40:30 CTOs Have Power! 47:06 Organizational Cynicism Where to find Bud• Website: https://nobl.io • LinkedIn: https://www.linkedin.com/in/budcaddell

    51 min
  2. We Sacrifice People for Performance. AI Is About to Make That Impossible ft. Margôt van Brakel

    APR 24

    We Sacrifice People for Performance. AI Is About to Make That Impossible ft. Margôt van Brakel

    This episode challenges a core assumption most tech leaders still operate under: that intelligence is our primary advantage. As AI systems begin to outperform humans in reasoning and decision-making, this conversation reframes AI not as another step in the industrial revolution, but as the start of an intelligence revolution. For CTOs and business leaders, this shift forces a deeper question. If machines can think, what is left for humans to lead? You’ll learn why performance-driven organizations are hitting a ceiling and why continuing to optimize for efficiency alone will limit long-term value. The discussion explores a transition already underway, from purely economic thinking toward purpose, connection, and responsibility. It also highlights how board-level conversations are evolving, moving from short-term business cases to broader value-based decisions that shape the future of the organization and society. The episode also brings this down to action. It outlines how leaders and teams can respond today through experimentation, curiosity, and intentional time spent on change rather than just execution. You’ll walk away with a clearer perspective on how to position your organization in a world where AI handles more of the thinking, and where leadership is defined by the ability to rethink strategy, culture, and human contribution at a fundamental level. Key Takeaways • AI is replacing not just manual work but cognitive work, forcing leaders to redefine human value beyond intelligence • Performance-driven cultures are reaching their limits; future organizations must prioritize meaning, connection, and long-term value • Strategy must shift from pure business cases to value cases, balancing today’s results with tomorrow’s impact • Leaders should foster experimentation by allocating time for learning, not just execution, to unlock AI’s real potential • Organizations that combine human strengths with AI effectively will outpace slower, legacy-driven competitors • The most critical leadership skill ahead is not control, but curiosity, responsibility, and the ability to rethink assumptions About MargôtMargôt van Brakel is a keynote speaker, author, and advisor with more than 20 years of experience guiding organizations through complex change. She works with boards and executive teams on the human side of AI — exploring how organizations can use technology as a means, not an end, and find the right balance between people and machines. Her work focuses on what it means to keep human value at the center of organizational transformation. Because this is not the next wave in the industrial revolution — it is a new one. And that changes everything about the questions leaders need to ask. Chapters00:00 Margôt Journey 05:42 Treating People as Machines 12:38 AI's Societal Impact 12:06 Ad 20:32 What is Your Responsibility? 26:00 What is Homo Conexus? 39:01 Ad 38:12 The Ugly Phase of Transformation 42:25 A Hopeful Perspective! Where to find Margôt• Website: https://margotvanbrakel.com • LinkedIn: https://www.linkedin.com/in/margotvanbrakel/ • Instagram: https://www.instagram.com/margotvanbrakel/

    48 min
  3. How User Psychology Grew a Dating App to 17 Million Users With Almost No Marketing Budget ft. Colin Hodge

    APR 17

    How User Psychology Grew a Dating App to 17 Million Users With Almost No Marketing Budget ft. Colin Hodge

    Colin shares the raw, behind-the-scenes reality of moving from a cushy engineering role at Microsoft to the high-stakes environment of a Silicon Valley accelerator. He discusses the pivotal "moment of liberation" when he admitted his initial startup idea was failing, a realization that cleared the path for him to co-found a viral sensation overnight. The conversation dives deep into the intersection of technology and user psychology. Colin explains how understanding human behavior allowed him to scale a product to 17 million users and later lead growth for a live-streaming giant in Asia with over 100 million users. He breaks down why technical leaders must look beyond the code to understand the "psychological levers" of their customers, whether they are building B2C dating apps or complex B2B platforms. Mark and Colin also explore the evolving role of the CTO in the age of AI. Colin argues that as AI makes the digital landscape noisier and more automated, the competitive advantage shifts to leaders who can empathize and connect with people. This episode is a masterclass in growth strategy, the psychology of negotiation, and why "judgment" is the most valuable asset a tech leader can bring to the boardroom. Key TakeawaysThe Power of Admitting Failure: Admitting a product is failing is often the necessary liberation to clear the path for a high-growth idea.Psychology Over Code: Growth is driven by understanding the psychological levers of acquisition and retention rather than just adding features.The AI Human Advantage: As AI automates digital noise, the primary competitive edge for leaders shifts toward human empathy and judgment.Strategic Friction: Real growth involves framing user choices and occasionally adding "good friction" to nudge people toward higher-value actions.Team Empathy as a Lever: Success requires framing technical decisions with the team's emotions in mind to ensure smooth execution.Pricing Strategy as Growth: Behavioral triggers, like the "second cheapest bottle" effect, can be applied to tech products to increase revenue. Chapters00:00 The 14 Year-old Company Owner 05:47 Launching DOWN 12:54 Ad 13:26 The Controversial "Bang With Friends" 17:42 "Outrageous Startup Growth" 24:18 Ad 24:29 Psychology as a Foundation! 28:14 Standing Out Through The AI Noise 30:10 Past Advice and Future Plans! 33:22 Behavioral Improvement and Empathetic Approach About ColinColin Hodge is a seasoned entrepreneur and growth expert with over 17 years of experience scaling businesses to over 100 million users. His expertise lies in organic growth, user psychology, and disruptive marketing. Colin co-founded and grew 'Bang with Friends' (later DOWN) to over 6 million users organically before selling it, and later re-acquired and grew it into a top 5 US dating app. He has also served on the board of a Silicon Valley social media company, contributing to over $200 million in annual revenue, and acted as Chief Growth Officer for 17Live, Asia's leading live-streaming app, where he led its US launch. Colin's approach is rooted in understanding user psychology to drive authentic, sustainable growth, and he is passionate about sharing his lessons with fellow founders and marketers. Where to find ColinWebsite: https://colinhodge.com/LinkedIn: https://linkedin.com/in/ckbhodgeInstagram: https://instagram.com/ckbhodgeColin's Book: Outrageous Startup Growth: Uncovering the Secrets of User Psychology to Scale Your Success: https://www.amazon.com/Outrageous-Startup-Growth-Uncovering-Psychology/dp/1394387334

    37 min
  4. Why 95% of AI Pilots Deliver Zero Business Impact and How to Fix Your Foundation ft. Matt Soltau

    APR 10

    Why 95% of AI Pilots Deliver Zero Business Impact and How to Fix Your Foundation ft. Matt Soltau

    Most AI projects don’t fail because of bad models. They fail because the data underneath is broken. Matt Soltau breaks down why “AI readiness” is really a data problem and why most organizations are building on fragile, disconnected systems that can’t survive outside a demo. From hidden data silos to untraceable pipelines and compliance risks, this conversation exposes the real reason AI initiatives stall and what CTOs must fix before scaling anything to production. You’ll learn how to move from spaghetti architecture to controlled, traceable data flows, why integration strategy matters more than the latest AI tool, and how to build a foundation that actually supports long-term AI value. If your board is pushing for AI but your systems feel messy underneath, this episode will show you where to start and what to avoid. Key TakeawaysWhy most AI pilots fail to deliver business impact despite working in sandbox environmentsThe hidden risk of disconnected data pipelines and how they break AI in productionEarly warning signs your data foundation is not ready for AIWhy point-to-point integrations create long-term complexity and technical debtHow to design scalable data architecture using integration layers instead of “spaghetti systems”A practical starting point: how to move from one controlled use case to enterprise-wide AI adoption About MattMatt Soltau is a Global Director of Strategy & Operations at IntelliPaaS, an AI‑ready data integration and workflow automation platform for enterprises and regulated organizations. With nearly a decade spent connecting siloed systems, automating complex processes and making data trustworthy for AI. He helps leaders turn fragile tech stacks into secure, compliant workflows that actually scale and drive real business results. Chapters00:00 Dangerous AI Assumption 09:37 Why Pragmatic Solutions aren't Enough 15:08 Ad 15:40 How Important is Compliance? 22:29 When Does the Problem Start? 28:59 Working with Enterprise Organizations 34:17 Dealing with Compliance Complexity 39:07 Ad 39:19 Expensive Integration Mistakes 46:26 Controlling Your Data Foundation! Where to find MattWebsite: https://www.intellipaas.io/LinkedIn: https://www.linkedin.com/in/soltaumatt/YouTube: https://www.youtube.com/@IntelliPaaS

    53 min
  5. The Software That Can’t Be Wrong: Building Fintech for Millions in Africa ft. Erioluwa Asiru

    APR 3

    The Software That Can’t Be Wrong: Building Fintech for Millions in Africa ft. Erioluwa Asiru

    What happens when you take a trust-based, offline financial system and turn it into software that people depend on with their money? In this episode, Erioluwa shares the real pressure behind building a fintech startup in Nigeria, where every product decision, line of code, and feature trade-off directly impacts user trust and financial safety. For startup founders, this conversation goes beyond fintech. It reveals what it actually takes to move users from familiar, manual systems into digital products, how to balance growth with risk, and why sometimes the best product decision is not building a feature at all. From early traction challenges to scaling a lean engineering team, this episode breaks down the realities of building something people rely on financially, not just functionally. You’ll also hear how trust becomes the real product, why simplifying solutions often beats complex engineering, and what changes when your users’ money, not just their attention, is on the line. Key TakeawaysWhy fintech changes engineering standards completely and why “good enough” code is never acceptableHow to balance product growth with fraud prevention and system riskA practical approach to deciding which features to build or reject based on risk vs returnHow to scale a lean engineering team without introducing unnecessary process overheadWhy raising the bar for users can be more effective than building complex safeguardsThe shift from writing code to leading people, making trade-offs, and owning outcomes About ErioluwaErioluwa Asiru is a software engineer, technology leader, and mentor, serving as CTO and Cofounder of Circle Funds. She leads the company’s technical vision, building scalable financial infrastructure and products that expand access to funding and wealth-building opportunities. Her work combines hands-on engineering with strategic leadership, ensuring reliable systems and strong product execution. Alongside her role as a founder, Erioluwa is a lead mentor at Data Epic, where she guides cohorts through intensive six-month programs in data and software engineering. She is passionate about developing practical skills, fostering confidence, and helping aspiring professionals transition into successful tech careers. Erioluwa has delivered a wide range of impactful solutions, including digital savings platforms, creator financing systems, admin portals, and automated data analysis tools. Driven by innovation, education, and economic empowerment, she is committed to building technology that creates real opportunities while mentoring the next generation of tech talent. Chapters00:00 What is Ajo? 06:56 Ad 07:28 Working in Nigerian Financial Technology 13:35 Fraud, Features, and Leadership 22:51 Ad 23:03 Complicated Solutions and Inspiration 26:38 The Future of Circle Funds 29:46 Mentorship Experience 31:05 You Need a Community! Where to find ErioluwaWebsite: https://circlefunds.ioLinkedIn: https://www.linkedin.com/in/asiru-erioluwa/

    33 min
  6. 3 Ways to Build AI Systems That Survive the Real World ft. Sairam Sundaresan

    MAR 27

    3 Ways to Build AI Systems That Survive the Real World ft. Sairam Sundaresan

    Most AI initiatives don’t fail because of weak models. They fail because they collapse under real-world complexity. This episode breaks down how CTOs and business leaders can design AI systems that survive messy data, unpredictable users, and production reality. You’ll learn how to shift from “build a model” thinking to system-level strategy, manage AI as a high-risk investment, and align business expectations with technical uncertainty. Key Takeaways • Why AI success depends more on system design than model performance • How to build guardrails, monitoring, and rollback into AI from day one • The “VC mindset” for AI investments and why most initiatives will fail before one works • How to align CEOs and boards around uncertainty, cost, and probabilistic outcomes • The real reason AI breaks in production and how to anticipate failure modes early • What skills modern AI teams need as roles shift from building models to orchestrating systems About SairamSairam Sundaresan is an AI Engineering Leader with over 15 years of R&D experience. Currently leading autonomous driving research at Valeo, he has a history of innovation at Intel Labs and Qualcomm, backed by a portfolio of patents and publications. Beyond his technical roles, Sairam is deeply invested in the growth of the AI ecosystem. He has mentored countless engineers, served as a Lead at the Frontier Development Lab (FDL) applying AI to space science, and actively advises business leaders on AI adoption. He is also the author of the book 'AI for the Rest of Us' (Bloomsbury) and writes Gradient Ascent, an illustrated newsletter read by over 25,000 subscribers. Through these channels and his LinkedIn following of over 100,000, he is one of the industry's most trusted voices for making AI accessible. Chapters00:00 Industry Real World Failures 05:26 Reliability of AI Models 11:24 Ad 11:57 "AI for the Rest of Us" 16:28 Starting With AI 24:54 Explaining AI to the Board 27:37 Ad 27:48 AI Unrealistic Expectations 32:42 What kind of People does AI Demand? 36:49 Keeping Up with AI 39:15 AI Predictions Where to find Sairam• Website: https://newsletter.artofsaience.com • LinkedIn: https://www.linkedin.com/in/sairam-sundaresan/ • Instagram: https://www.instagram.com/artofsaience/ • YouTube: https://www.youtube.com/@artofsaience • His Book: https://www.amazon.com/AI-Rest-Us-Illustrated-Introduction/dp/B0F29THNLT/

    43 min
  7. AI Risk Is a Design Problem: 3 Questions Every CTO Should Ask Before Their Next AI Release ft. Jill Stover Heinze

    MAR 20

    AI Risk Is a Design Problem: 3 Questions Every CTO Should Ask Before Their Next AI Release ft. Jill Stover Heinze

    Most AI strategies fail before anything ships, not because of the tech, but because leaders never test assumptions against reality. In this episode, CTOs will learn how to ground AI strategy in real user behavior, reduce risk early, and avoid costly AI failures before they scale. Jill Stover-Heinze breaks down how generative AI changes the risk model, why non-deterministic systems demand new leadership thinking, and how CTOs can turn governance, user research, and risk into a competitive advantage instead of a bottleneck. Key Takeaways Why most AI strategies fail before build and how to validate ideas against real user behaviorHow generative AI changes risk and why non-deterministic systems require new leadership thinkingHow to use risk and governance as a design tool instead of a compliance exerciseWhy product-market fit still kills AI initiatives and how to avoid building the wrong thingWhat to ask your board and teams to move fast without falling into AI hype and costly mistakes About JillJill Heinze helps product leaders make smarter AI decisions through strategic intelligence and ground truth research. As founder of Saddle-Stitch Consulting, she brings 20 years of user research and competitive intelligence experience to help organizations navigate AI uncertainty, revealing what competitors miss and avoiding expensive mistakes before they happen. She serves as Responsible AI Program Director for The American College of Financial Services and hosts Responsible Tech Talks on LinkedIn Live. Chapters00:00 The Ground Truth 04:38 AI's Hidden Consequences (NIST) 12:47 Ad 13:19 Approaching AI as a CTO 18:45 FOMO in the Corporate World 22:57 Keeping Up with AI 28:42 Ad 28:53 Effectively Using AI 37:27 Talk to Your People! Where to find JillWebsite: https://www.saddlestitchconsulting.comLinkedIn: https://www.linkedin.com/in/jill-stover-heinze/Instagram: https://www.instagram.com/jill_saddlestitchconsult/YouTube: https://www.youtube.com/@JillHeinze-SaddleStitchConsultFacebook: https://www.facebook.com/profile.php?id=61581363390571TikTok: https://www.tiktok.com/@jill_saddlestitchconsult

    42 min
  8. AGENTS.md Won’t Save You: Design AI Systems You Can Actually Control ft. Craig Kaplan

    MAR 13

    AGENTS.md Won’t Save You: Design AI Systems You Can Actually Control ft. Craig Kaplan

    AI is moving from copilots to autonomous agents, and most tech leaders are not prepared for what that shift means. Craig walks through the real risks behind superintelligence, why AI checking AI is becoming inevitable, and how CTOs and CIOs can design safer, more resilient systems before autonomy outpaces human oversight Rather than focusing on hype, this episode dives into the alignment problem, the limits of guardrails, and why monolithic black box models may be the wrong long term architecture. You will hear a practical path forward for tech leaders who are already overwhelmed by AI generated code, agent frameworks, and rapidly evolving models If you are leading engineering, AI, or technology strategy, this episode will challenge how you think about safety, governance, autonomy, and the future role of the CTO in an AI driven world. Key Takeaways Why AI checking AI is not optional as code generation and autonomy scaleWhat the alignment problem really means for enterprise technology leadersThe limits of guardrails and why prevention at design stage beats patching at deploymentHow democratic architectures of multiple agents can reduce systemic riskWhy vendor agnostic, multi model strategies increase resilience and strategic controlHow to embed company values into AI systems through training, memory, and architectureWhat P(doom) represents and why many leading researchers assign it far higher risk than most executives assume About CraigDr. Craig A. Kaplan is a renowned expert in artificial intelligence, artificial general intelligence, and superintelligence, with a focus on collective intelligence and quantitative modeling. He is the Founder of Superintellligence.com and CEO and founder of iQ Company, a consulting firm dedicated to advanced AGI and SI systems. Previously, he founded PredictWallStreet, a financial services firm that powered top hedge fund performance by leveraging the collective intelligence of retail investors. Dr. Kaplan has authored a book, published extensively in scientific journals, and holds numerous patents on AI-related technologies. Chapters00:00 How far is AGI? 06:55 What is P(doom)? 16:43 AI Reviewing AI Output 20:54 Dealing with Bad Actors (Human or AI) 25:36 Approaching AI as a Small Scale CTO 30:43 Democracy of AI Agents 35:15 AI Safety Conferences 40:03 AI Models, Open-Source or Big Company? 45:05 Is AI Adoption Keeping Up? Where to find CraigLinkedIn: https://www.linkedin.com/in/craigakaplanWebsite: https://www.superintelligence.comWebsite: https://iqco.comYouTube: https://www.youtube.com/@iqstudios1

    52 min
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About

The CTO Compass is a podcast about CTO, CIO, and tech leadership - on strategy, scaling, teams & bringing clarity to technology leadership for real boardroom impact. Hosted by Mark Wormgoor, each episode features candid conversations with experienced CTOs, CIOs, and senior tech leaders from startups through to large enterprises. The focus is on the real work of leading in tech: – Setting clear tech strategy that aligns with business goals – Scaling teams and culture – Making high-stakes decisions under pressure – Navigating the transition from hands-on engineer to executive leader This is not a hype show, nor a theoretical leadership podcast. Guests share hard-won lessons, mistakes, and practical insights from the moments that mattered most - when clarity was missing, heavy decisions needed to be made, and leadership was tested. If you’re a CTO, CIO, or tech leader looking to sharpen your thinking, increase your influence, and create real impact in the boardroom, The CTO Compass is built for you.

Information

  • Creator
    Mark Wormgoor
  • Years Active
    2025 - 2026
  • Episodes
    33
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Tairi
  • Show Website
    The CTO Compass