The CTO Compass

Mark Wormgoor
  • 5.0 (1)
  • TECHNOLOGY
  • UPDATED WEEKLY

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

    5D AGO

    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
  2. 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
  3. 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
  4. Why Treating AI Like Software will cause Most AI Initiatives to Fail ft. Stephanie Sylvestre

    MAR 6

    Why Treating AI Like Software will cause Most AI Initiatives to Fail ft. Stephanie Sylvestre

    AI is not just another tool. It is reshaping leadership, strategy, and the future of work. Stephanie Sylvester explains why most AI initiatives fail, why middle management is most at risk, and how CTOs and CIOs can use AI to create faster strategy clarity, stronger teams, and real business impact. If you are leading AI inside your organization, this conversation will challenge how you think about automation, culture, and staying relevant in an AI-driven economy. Key Takeaways • Why AI initiatives fail when treated like software instead of a leadership and culture shift • How C-level leaders can use AI to create faster strategy clarity and execution • Why middle management roles are most exposed and how to reposition them around coaching and people development • How AI can improve team performance and reduce internal friction • Why clean data and context determine whether AI creates value or chaos • How tech leaders should think about personal employability and continuous learning in an AI-driven economy About StephanieStephanie is a technology leader who helps organizations turn complex AI and software problems into clear, actionable strategies. With a track record of partnering closely with CTOs and engineering teams, she specializes in scaling systems, improving developer velocity, and aligning technical roadmaps to business outcomes. On CTO Compass, she’ll share practical insights from the field on building resilient architectures, navigating AI adoption, and leading teams through rapid change. Chapters00:00 Managing AI with a Human Perspective 06:06 Avatar Buddy 14:04 Automation using AI 24:47 Getting People Into AI 31:05 Working with Smaller Systems 35:16 C-level People and Personal Growth 43:42 What Does the Future Look Like? Where to find Stephanie• Website: https://avatarbuddy.ai • LinkedIn: https://www.linkedin.com/in/stephanie-a-sylvestre • Instagram: https://instagram.com/avatar_buddyai • YouTube: https://www.youtube.com/channel/UC7WJI0FupsR6CTMmI6-MEeQ My Socials• Website: https://tairi.co • LinkedIn: https://www.linkedin.com/in/mwormgoor • Instagram: https://www.instagram.com/markwormgoor Contact Us• Business Email: team@tairi.co

    47 min
  5. Why CTOs Burn Out when the Pressure to Deliver Keeps Rising ft. Andrew Hinkelman

    FEB 27

    Why CTOs Burn Out when the Pressure to Deliver Keeps Rising ft. Andrew Hinkelman

    CTOs and CIOs are facing relentless delivery pressure as teams shrink, AI accelerates expectations, and urgency becomes the default operating mode. In this episode, you will learn how constant exhaustion and apathy signal deeper leadership risk, why staying hands-on quietly destroys strategic capacity, and how small changes in delegation, prioritization, and ownership can help tech leaders move from reactive sprinting to sustainable executive leadership. Key Takeaways • Why rising delivery pressure is burning out even highly capable CTOs and CIOs • How the hands-on fixer mindset breaks down at scale and increases risk • The early warning signs of burnout most tech leaders ignore until it is too late • How to delegate real ownership without losing control or accountability • What sustainable, long-term tech leadership looks like in high-velocity environments About AndrewAndrew Hinkelman is a certified Executive Coach and recent CTO and COO. He has more than 25 years of experience in the Technology and Financial Services industries across roles in IT, Product Management, and Business Intelligence along with consulting and fractional roles. Andrew helps high-achieving executives—CEOs, CTOs, and their teams—master the balance between operational demands and strategic growth. He uses an "inside-out" framework with his clients, meaning that we must understand self-leadership and self-improvement before we can effectively lead others. Andrew has worked with global brands and high-growth companies like AWS, Sony, AirBnB, LinkedIn, Stripe, Coinbase, Reddit, Twitch, Tripadvisor, Hello Fresh, and Gilead, helping their leaders overcome challenges, foster collaboration, and elevate their impact. Andrew lives in the Seattle area with his family where he spends an enormous amount of time on a bike or paddleboard and sneaking out to the mountains. Chapters00:00 What makes a Successful CTO 05:48 "I need to fix everything" 10:56 Delivery Expectations and Overwork 21:54 What Burnout Looks Like 26:40 When Standard Training Isn't Working 33:05 Bringing People into the Culture 37:54 TAKE CARE OF YOURSELF! Podcast mentions• Website: https://ctolunches.com/ Where to find Andrew• Website: https://www.pri-1.com/ • LinkedIn: https://www.linkedin.com/in/andrewhinkelman/ My Socials• Website: https://tairi.co • LinkedIn: https://www.linkedin.com/in/mwormgoor • Instagram: https://www.instagram.com/markwormgoor Contact Us• Business Email: team@tairi.co

    46 min
  6. Why Enterprise AI Keeps Disappointing (hint: CoPilot isn’t the Problem) ft. Santosh Kaveti

    FEB 20

    Why Enterprise AI Keeps Disappointing (hint: CoPilot isn’t the Problem) ft. Santosh Kaveti

    Most CTOs and CIOs are not behind on AI because they chose the wrong model. They are behind because their data, culture, and workflows are not ready. In this episode of The CTO Compass, Mark Wormgoor speaks with Santosh Kaveti, CEO of ProArch, about what it really takes to scale AI in large enterprises. They break down why AI pilots stall, why data lakes did not solve data readiness, and how tech leaders can move from experimentation to real business impact in 90 days or less. The conversation also covers Microsoft Copilot, enterprise data governance, AI security and compliance, and how CIOs and CTOs should respond when boards demand AI results. If you are a CTO or CIO under pressure to deliver AI outcomes instead of demos, this episode offers a practical, no-hype playbook. Key Takeaways for CTOs and CIOs Why AI adoption fails without strong data readiness and ownershipWhat “data as a product” looks like in practiceHow to move from AI pilots to production in four to six weeksWhy Copilot often struggles and how to unlock real productivity gainsHow to measure AI ROI beyond licenses and usage metricsWhy model-agnostic architecture matters for enterprise AI About SantoshWith over 18 years of experience as a technologist, entrepreneur, investor, and advisor, Santosh Kaveti is the CEO and Founder of ProArch, a purpose-driven enterprise that accelerates value and increases resilience for its clients with consulting and technology services, enabled by cloud, guided by data, fueled by apps, and secured by design. Santosh’s vision and leadership have propelled ProArch to become a dominant force in key industry verticals, such as Energy, Healthcare & Lifesciences, and Manufacturing, where he leverages his expertise in manufacturing process improvement, mentoring, and consulting. Chapters00:00 Knowing When You're in the Wrong Direction 07:44 What is Data Readiness in AI? 12:49 Where Do You Start with AI Data? 17:43 AI Implementation in Your Business 26:11 Microsoft Copilot is Overtaking! 37:04 AI Enterprise Adoption 43:53 Leveraging AI for Big Changes Where to find SantoshWebsite: https://www.proarch.com/LinkedIn: https://www.linkedin.com/in/santoshkaveti/ My Socials• Website: https://tairi.co • LinkedIn: https://www.linkedin.com/in/mwormgoor • Instagram: https://www.instagram.com/markwormgoor Contact Us• Business Email: team@tairi.co

    46 min
  7. The Hidden Complexities of SaaS Pricing, CPQ, and Quote-to-Cash ft. Tina Kung

    FEB 13

    The Hidden Complexities of SaaS Pricing, CPQ, and Quote-to-Cash ft. Tina Kung

    Revenue systems are becoming a major source of complexity in modern SaaS and AI companies. As CPQ, pricing, quoting, and billing evolve, they often slow decisions and execution instead of enabling growth. In this episode of The CTO Compass, Tina Kung, Founder and CTO of Nue, shares lessons from building revenue systems at Salesforce, Zuora, and Neocrm. The conversation explores why revenue infrastructure shapes strategic clarity and boardroom impact, why most enterprise AI stops at summaries, and how CTOs can design systems that scale without slowing the business down. You'll learn: Why CPQ and quote-to revenue systems often slow decisions as SaaS and AI companies scaleHow pricing flexibility and personalization create hidden complexity that impacts execution and strategyWhy revenue systems should be treated as core technical infrastructure with direct boardroom impactWhat most enterprise AI gets wrong by stopping at summaries instead of removing operational workHow CTOs can simplify revenue workflows to improve clarity without triggering a large transformation project Chapters00:00 Handling Business Overload 07:09 Simplifying the Process 14:47 The Hurdles of Implementation 18:31 Problems with Old Contracts 23:11 OpenAI's Strict Timeline 25:54 Complexity under Simplicity 31:26 Implementing AI 35:40 What's Next? About TinaTina Kung has over 20 years of experience in the opportunity-to-cash space. Before co-founding Nue.io, she served as VP of Products and Engineering at Neocrm — the largest CRM in China — and held engineering leadership roles at Salesforce CPQ, Zuora, and Oracle CPQ. As Nue’s CTO, Tina is reimagining how modern businesses run revenue. She founded Nue to solve the painful complexity she witnessed firsthand at companies like Salesforce and Zuora. Her vision is clear: to build a unified, AI-powered platform that makes revenue operations elegant, intelligent, and beautifully simple. Under her technical leadership, Nue is powering the next generation of SaaS and AI companies with a Salesforce-native quote-to-revenue platform that unifies pricing, quoting, billing, and analytics in real time. Where to find TinaLinkedIn: https://www.linkedin.com/in/tinakung/Website: https://nue.io

    42 min
  8. Why Smart Tech Leaders Become the Bottleneck (and How to Get Out of the Weeds) ft. David Hori

    FEB 6

    Why Smart Tech Leaders Become the Bottleneck (and How to Get Out of the Weeds) ft. David Hori

    Most CTOs and tech leaders don’t think they’re the bottleneck. They think they’re being responsible: staying close to the details, protecting quality, moving fast. But from a buyer’s perspective, that same behavior often is a sign of risk: decisions that don’t scale, teams that depend too heavily on one person, and execution that quietly slows down as the organization grows. In this episode of The CTO Compass, Mark sits down with David Hori, an operator-turned-acquirer with more than 25 years of experience scaling companies and taking three startups to exit. Today, David doesn’t just advise leaders, he buys businesses. That gives him a rare view on what breaks as companies scale, and why strong leaders so often become the constraint without realizing it. Together, they unpack: how CTOs and tech leaders unintentionally become bottlenecksthe difference between delegation and abdicationhow to work effectively with visionary CEOs without drowning in continuously changing prioritieswhy AI often amplifies leadership problems instead of fixing themand what buyers look for when evaluating whether a business can scale or exit Chapters00:00 When the Leader is the Bottleneck 07:58 Being Open to Change 15:36 Handling Visionaries 19:12 How to Approach Delegation 26:27 AI in Today's Business Landscape 37:14 Is Your Business Going to be Bought? 39:55 Realizing Where You're at! About DavidDavid buys profitable local businesses, typically with 10-200 employees or $3–$15M in revenue. He is not private equity chasing a quick flip. He focuses on preserving what founders built, including their people, culture, and legacy. He also advises a small number of established owners, but he thinks like a buyer, not a consultant. That means direct, honest assessments with no busywork and no slide-deck frameworks that fail in practice. Just proven systems that help owners step back or exit entirely. Whether he is buying a business or advising an owner, David brings an operator’s perspective. Fast decisions, practical solutions, no fluff. Where to find DavidLinkedIn: https://www.linkedin.com/in/iamdavidhori/Instagram: https://www.instagram.com/toplineops/Topline Operators: https://www.toplineops.com/YouTube: https://www.youtube.com/@toplineops

    43 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
    28
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Tairi
  • Show Website
    The CTO Compass