The CTO Compass

Mark Wormgoor

The CTO Compass is a podcast for CTOs, CIOs, IT directors, and everyone leading technology teams. The hardest part of leading in tech was never the technology. It's leading people, growing into the job while everyone assumes you already know how to do it. That's what this show is about. Every guest brings one lesson: the one thing they'd teach every tech leader, backed by their real stories. The growth, the setbacks, and the decisions that made them the leader they are today. Alongside the interviews, there are solo episodes where Mark shares the leadership lessons from his own career and his executive coaching. This is not a hype show, and it's not theoretical leadership content. Real stories, real mistakes, and lessons you can use. Your host: Mark Wormgoor. He spent 30 years in technology, six of them running global IT teams at JDE, and today he works as an executive coach for IT leaders. If you lead in tech, or you want to, The CTO Compass is built for you.

  1. Jun 26

    What to Do When Your Team Is Scared AI Will Replace Them ft. Angela Mulrooney

    In this season finale of The CTO Compass, host Mark Wormgoor sits down with Dr. Angela Mulrooney, an entrepreneur who has successfully built five companies and sold four. Angela shares her remarkable journey of navigating sudden career shifts and personal identity crises, proving that major industry turns and external downturns are often the best moments for finding unexpected opportunities. For technology leaders and business owners, this conversation shifts focus away from standard growth tactics toward the fundamentals of personal adaptability and sustainable scaling. Angela breaks down her framework for identifying your unique genius. She details how to package that expertise clearly so the market understands your outcome, allowing you to remove yourself as the operational bottleneck to build momentum effectively. The discussion highlights why rapid industry shifts demand that leaders reconsider their current trajectory and step into self-reliance rather than relying on comfortable corporate titles. The episode also explores the human side of steering teams through rapid technological changes, such as the current acceleration of artificial intelligence. Angela challenges conventional thinking about career progression and ageism, offering practical tools to help leaders refine their focus. By prioritizing alignment with your highest potential and leading with empathy, you can move your engineering teams out of fear states and into productive action. Key Takeaways • Use the sticky note exercise to identify your top three capabilities for the next five years, creating absolute clarity on what to accept and what to reject. • Guide your engineering team out of a state of anxiety during rapid artificial intelligence changes by using human kindness and open conversations. • Identify your unique areas of genius and remove yourself as the operational bottleneck so your business can grow. • Reframe external market downturns and personal identity crises as moments to step back, get calm, and locate new business directions. • Recognize why current economic shifts make corporate dependency riskier than stepping into entrepreneurship. • Apply your accumulated insights to new industries, knowing that your strategic frameworks and diagnostic skills are never lost. About AngelaDr. Angela Mulrooney is known globally as The Arsonist. She works with highly accomplished professionals who are questioning their relevance in a rapidly changing world. Not because they lack experience or results. But because the rules that once rewarded expertise have shifted. After a career ending injury forced her out of dentistry, Angela rebuilt by creating and selling four companies across four industries. Each was successful. Each was rooted in a different skill set. Over time, she saw the deeper pattern. Relevance is not about doing more or branding louder. It is about identity. When markets change, the work that survives is not the most polished. It is the most grounded in lived experience, judgment, and trust. Today, Angela helps leaders architect relevance from the inside out. Her work centers on Identity Architecture. The structure that connects who you are, how you think, and why your perspective still matters. From there, visibility and personal branding become natural expressions, not forced performances. Angela is known for burning away what no longer fits and helping people rebuild identities the machine cannot replicate. Chapters00:00 Working Through Crises 09:34 Ad 10:07 You're Skills Matter! 13:07 AI as a Partner, Not a Replacement 15:41 Fear of Change 19:22 Ad 19:34 Helping People Through Change 22:12 Kindness Through Fear 23:51 Falling In Love with Your Idea 26:59 The Sticky Note Exercise 28:43 Unleashing Influence Where to find Angela• Website: http://app.unleashinginfluence.com/v3 • LinkedIn: https://www.linkedin.com/in/angelamulrooney

    What to Do When Your Team Is Scared AI Will Replace Them ft. Angela Mulrooney

  2. Jun 19

    Why The Best Engineering Managers In 2026 Code More, Not Less ft. Alex Ponomarev

    Alex Ponomarev, founder of Volt and author of the Thriving in Engineering Substack, joins host Mark Wormgoor to decode the reality of the AI talent gap. They explore what it takes to build AI-native engineering teams and how the role of the tech leader is fundamentally changing. Alex shares his personal transition from an overwhelmed engineering manager back to a hands-on contributor, highlighting how modern coding assistants allow leaders to analyze massive codebases quickly. The conversation dives deep into the mindset shift required for modern tech executives. Listeners will learn why managers must stop delegating from afar and instead get inside the development process by actively experimenting with new AI tools. Alex breaks down how automating mechanical tasks like meeting summaries can free up limited time for actual strategic leadership and team building. Finally, they tackle the future of the engineering workforce and career progression. Discover why junior engineers are more crucial than ever for bringing fresh perspectives and new experimental energy to your team. The episode also highlights why soft skills and end-to-end "agency" are the most critical traits for developers navigating this rapid technological shift. About AlexAlex Ponomarev is the founder and CEO of Volt, with 20+ years building and scaling global technology companies. He leads teams building AI-native intelligence layers for venture capital firms. His focus is bridging human expertise with AI to improve decision-making and performance. Through his publication Thriving in Engineering, he shares practical frameworks that help engineering leaders navigate complexity and build high-performing teams. Chapters00:00 Coding in 2026 08:56 Utilizing Your Time! 13:32 Ad 14:04 The Truth about AI Agents 16:22 Handling Multiple Teams 17:56 Keeping Up With Modern Technology! 23:01 What Skill Should You Develop? 28:10 Ad 28:21 The Future of Engineering Managers 32:04 Growing in Complexity Where to find Alex• LinkedIn: https://www.linkedin.com/in/alexponomarev/

    Why The Best Engineering Managers In 2026 Code More, Not Less ft. Alex Ponomarev

  3. Jun 12

    People Over Clients Over Projects (Why Most Agencies Rank It Wrong) ft. Dominic Tancredi

    Most digital agencies do not survive past year five. Dominic Tancredi has been running Dom & Tom for 17 years, navigating every technology wave from the birth of mobile to the current AI agent explosion. Surviving that long requires more than just technical capability. It requires making painful leadership decisions when the pressure is highest. Mark Wormgoor pressure-tests Dominic's contrarian approach to technology and team building. They discuss the realities of the current tech market, breaking down how enterprise, mid-market, and startup boardrooms are reacting to the AI shift. Dominic also shares a vulnerable story about a failure in judgment when a major client demanded a brutal deadline, and the hard lesson he learned about choosing his people over a project. Dominic brings nearly two decades of experience helping founders and CTOs build digital products that matter. If you are looking for clarity on how to navigate the increasing cognitive load of tech leadership, this conversation delivers. Subscribe to The CTO Compass on Apple Podcasts or Spotify so you never miss an episode. Key Takeaways • Prioritizing your engineering team over demanding clients is essential, even if it means losing a major account. • Refusing to commit to a single technology stack gives you the flexibility to solve diverse business problems effectively. • Large organizations are cutting headcount and relying on AI agents to fill the gaps, which creates massive opportunities for fast-moving intrapreneurs. • Medium-sized businesses face the highest market pressure right now because they are caught between economic volatility and the urgent need to adopt new workflows. • AI has accelerated product execution so significantly that a founder's primary challenge is now marketing and finding real users. • The cognitive load on tech leaders is shifting from writing code to reviewing output as autonomous agents begin generating daily pull requests. About DominicDominic Tancredi is the Co-Founder and CEO/CTO of Dom & Tom, a digital product agency with over 17 years of experience designing and building scalable web, mobile, and emerging technology platforms. He specializes in bridging product strategy, user experience, and engineering to help organizations launch and evolve high-impact digital products. With a background in both computer science and theater, Dominic brings a unique perspective to storytelling in product design - combining technical rigor with human-centered thinking. He has led initiatives for startups, enterprise organizations, and government entities, with a focus on innovation, AI integration, and user-centric solutions. At Dom & Tom, his team follows a structured 5D methodology - Define, Discover, Design, Develop, Deploy - to ensure products are strategically aligned, technically sound, and built for long-term success. Chapters00:00 Do Good, Be Good! 05:55 Widening Your Curiosity 07:56 Keeping Up with Technology 10:07 The Contrarian's Mindset 13:51 Ad 14:22 Surviving 17 Years! 18:24 Biggest Mistakes and Small Ws 24:42 Long Term Professional Relationships 27:48 Ad 28:00 Tech Market Cross Section! 37:12 Agents, Assistants, and Reviewers 44:32 Working With Your Team Where to Find Dominic• Website: https://domandtom.com/ • LinkedIn: https://linkedin.com/in/domtancredi

    People Over Clients Over Projects (Why Most Agencies Rank It Wrong) ft. Dominic Tancredi

  4. Jun 5

    The Model Doesn't Matter: What Actually Creates 10x AI Productivity ft. Clive Moore

    Technology decisions feel heavy when AI and data privacy collide. In this episode of The CTO Compass, I sit down with Clive Moore, a UI/UX designer with 25 years of experience who became the founder of GPT Studio and Workilo. After experiencing a severe ransomware attack on his agency's self-hosted GitLab instance, Clive shifted his focus to building safer infrastructure for agencies and businesses. We discuss why the underlying AI model does not actually matter as much as the foundation you build it on. Clive details his method of keeping data private by relying on Canadian data sovereignty laws rather than default US cloud services. He also explains why setting strict guardrails on AI agents and keeping a human in the loop is the only way to avoid contributing to the growing volume of AI-generated slop online. Listeners will discover practical ways to adopt AI without getting locked into a single platform. You will learn how pre-trained agents can handle real business workflows, such as checking construction invoices for fraud, while maintaining your brand voice and data security. If you want to move past the hype and deploy AI safely, this episode provides a clear roadmap. Key Takeaways The specific AI model you choose matters less than the infrastructure and guardrails you build around it.Hosting data on localized servers provides data sovereignty and protects corporate information from broad surveillance laws like the US Patriot Act.Fully autonomous agents still confabulate, making human oversight necessary to maintain quality and prevent AI slop.Building an LLM-agnostic system lets you switch between models like OpenAI, Claude, and Cohere without losing your historical data.You can eliminate the garbage output problem by pre-training agents with established standard operating procedures and specific brand voices.Practical AI adoption focuses on tight operational tasks, like auditing supplier invoices for erroneous charges or managing an executive calendar. About CliveClive Moore is a Canadian entrepreneur and agency veteran with 25+ years building brands and creative teams. He's the founder of GPT Studio, a Canadian-hosted, model-agnostic enterprise AI orchestration layer built for teams that need speed without surveillance. His work challenges the assumption that better AI means better models—proving that 10–15x gains come from better infrastructure around existing models. He calls this "infrastructure over magic." GPT Studio is built on Canadian soil, for organizations that treat data sovereignty as architecture, not compliance. Chapters00:00 The Designer's Approach 05:53 gptstudio and workilo 13:15 Ad 13:47 AI Adoption Fear 16:41 gptstudio's Userbase 18:55 Ad 19:06 Servers and AI Agents 25:08 AI Platform Locking 27:50 Teaching in the Age of AI 31:08 What's Next? Where to find Clive• Website: https://gptstudio.workilo.io/ • LinkedIn: https://linkedin.com/in/clivemoore • Instagram: https://instagram.com/clivemoore1979

    The Model Doesn't Matter: What Actually Creates 10x AI Productivity ft. Clive Moore

  5. May 29

    Stop Panic-Buying AI: The Silver Bullet Myth That's Making You Slower ft. Asim Kumar

    Mark Wormgoor sits down with network architecture veteran Asim to unpack what 32 years in the technology trenches teaches you about surviving massive industry shifts. Asim earned his CCIE certification in the year 2000, right before the dot-com bubble burst, and later pursued an MBA and CFA prep right into the teeth of the 2008 financial crash. Now, as the industry faces the wave of generative AI and agentic automation, Asim shares how those historical failures forced him to stop buying the industry panic and start building personal resilience. Mark and Asim dive deep into the reality of "vibe coding" and agentic AI, exploring how non-technical founders and seasoned engineers alike are building entire platforms over a single weekend. But with rapid deployment comes massive risk. They discuss the critical "black box problem," why security must be built-in by design rather than bolted on as an afterthought, and why the ultimate tech leadership superpower in the era of AI isn't prompt engineering, it's governance and human oversight. Whether you are a founder rushing a new build to market or an enterprise executive steering a legacy modernization project, this conversation serves as a practical blueprint for balancing your people, processes, and technology when the ground beneath you is shifting fast. About AsimAsim Kumar is a Solution Architect who bridges the gap between deep technical systems and human psychology. Holding the industry’s highest credentials (CCSP, CISSP, CCIE, PMP, MBA, MSIS), I spent 30+ years "unblocking" multimillion-dollar networks for global enterprises. But his most profound expertise comes from a personal battle. For two decades, he lived a dual life—a celebrated Tech Consultant by day, but secretly "blocked" by fear and significant losses in the financial markets by night. This struggle taught him a critical paradox: You cannot fix a blocked mindset with a faster technology. Now, as the author of UNBLOCKED: The Power of Real Intelligence in the Era of AI, he challenge the modern obsession with technology. he helps leaders and entrepreneurs move from "Fear-Based Decision Making" to strategic clarity. His core message is that while Artificial Intelligence offers speed, only Real Intelligence (empathy, discipline, and focus) provides direction. Chapters00:00 What's New In The Era of AI? 11:26 Worldwide Technology 13:51 Ad 14:21 Cybersecurity In The Age of AI 16:12 Panic Selling vs Panic Buying 22:36 Applying AI in Today's Market 29:04 Ad 29:15 The Problem With Vibe Coding 33:29 Who is "UNBLOCKED" for? 37:06 What's the Next Step? Where to find Asim• Website: https://avignallc.com/ • LinkedIn: https://www.linkedin.com/in/asim-avigna/ • Instagram: https://www.instagram.com/asim.avigna • YouTube: https://www.youtube.com/@asim-avigna

    Stop Panic-Buying AI: The Silver Bullet Myth That's Making You Slower ft. Asim Kumar

  6. May 22

    Why Dropping AI Into a Broken Process Makes Everything Worse ft. Mike Toguchi

    Most technology leaders start by looking at the tool. Mike Toguchi, Chief Strategy Officer at Tectonic, argues that is the wrong beginning. If you drop AI into a broken process, you don't fix the problem, you only accelerate the failure. Mike joins the conversation to discuss why the most critical technology decisions often happen outside the engineering team and how to build systems that scale without drowning in technical debt. Mike brings a unique perspective as a strategist who studied government and politics rather than computer science. Having spent 23 years evolving with the same company, he has seen the transition from simple web digitization to the current age of AI. We talk about the "bad cop" role a partner must play in forcing standardization across departments and why the biggest hurdle to digital transformation is rarely the code, but the legacy silos and people who protect them. We also dive into the reality of AI governance and policy. Mike shares how his team navigates the tension between rapid innovation and protected data in high-stakes environments like university disability services. It is a discussion about judgment, critical thinking, and why the next two years will separate the leaders who aggressively pursue change from those who simply try to limp along. About MikeMichael "Mike" Toguchi is the Chief Strategy Officer at Tectonic, formerly eResources, where he leads platform direction for application management systems that streamline complex processes like scholarships, grants, admissions, and accessibility services. With over 25 years of experience driving digital transformation for universities, non-profits, foundations, and associations, Michael specializes in simplifying internal workflows to help mission-driven teams reduce manual work, scale sustainably, and strengthen compliance. His work powers organizations including Stanford, UC Davis, PG&E, the Roddenberry Foundation, and Google’s Certified Innovator Program. At the core of his mission is a commitment to building technology that enables teams to focus less on managing systems—and more on delivering meaningful impact. Chapters00:00 Politics to Technology?!??! 06:08 What is Tectonic? 11:55 Ad 12:27 23 Years of Growth and Change 15:41 The Value of People 19:51 Customization Accommodation 26:44 Ad 26:55 Who Makes Technology Decisions? 28:25 AI Implementation and AI Policy Issues 36:36 The Future of Tech Where to find MikeWebsite: https://www.teamtectonic.com/LinkedIn: https://www.linkedin.com/in/miketoguchi/

    Why Dropping AI Into a Broken Process Makes Everything Worse ft. Mike Toguchi

  7. May 15

    3 Critical Career Mistakes Engineering Leaders Make ft. Limor Bergman Gross

    This episode focuses on the transition from technical execution to organizational impact. Limor Bergman Gross shares how many engineering managers get stuck because they focus solely on being good at their jobs. She explains that promotion to director or VP levels requires a shift in focus. It is no longer about how well you code or manage a sprint, but about how well the organization knows your impact. The conversation explores the "trust gap," where leaders mistakenly believe their direct manager is the only one who needs to see their value. Limor and Mark discuss the necessity of building strategic relationships across the company. They provide a framework for stakeholder management that relies on curiosity and solving business problems rather than internal politics. This approach helps technical leaders gain the visibility needed for executive roles. Finally, the discussion covers the practicalities of leadership like delegating effectively and giving direct feedback. Limor highlights the "busy trap" where leaders fill their schedules with low-impact tasks to feel productive. She offers strategies for pushing back on non-essential requests to create space for strategy. The episode concludes with advice on using the Radical Candor framework to build high-performing teams through clear, empathetic communication. About LimorLimor Bergman Gross is a former Director of Engineering with over 20 years of experience across software engineering, engineering management, and organizational leadership. She has led teams through growth, scaling pressure, and complex delivery environments, working closely with CTOs and senior executives to align technology, people, and business priorities. Known early in her career as the “reliable leader” and escalation point, Limor learned firsthand how high-performing leaders can unintentionally become bottlenecks at scale. Today, she works as an executive leadership coach with senior engineering leaders and CTO-adjacent roles, helping them transition from hands-on decision-makers to strategic leaders who build teams that think, decide, and execute independently. Her work focuses on decision-making, ownership, leadership culture, and the real trade-offs tech leaders face as they move from execution to executive impact. Chapters00:00 Software Engineer to Leadership 06:33 Getting Promoted 14:39 Ad 15:11 What are You Busy With? 20:26 How to Give Feedback 22:53 Female Engineers! 24:50 Coaching The Executives 29:08 Ad 29:19 Getting Unstuck 36:54 Working with Different People 40:45 What is Your Impact? Where to find Limor• Website: https://limorbergman.com/podcast/ • LinkedIn: https://www.linkedin.com/in/limorbergman/ • Instagram: https://instagram.com/limorbergman • YouTube: https://www.youtube.com/@LimorBergman

    3 Critical Career Mistakes Engineering Leaders Make ft. Limor Bergman Gross

  8. May 8

    Your AI Strategy Will Fail for the Same Reason Your Last ERP Did ft. Abhijit Verekar

    Most large-scale technology projects don't fail because the software is broken; they fail because the incentives are misaligned long before the first line of code is written. AV, founder of Avira Advisors and author of Start at Zero, joins Mark Wormgoor to discuss why massive ERP implementations, like the Birmingham City Council’s £200 million disaster spiral out of control and how tech leaders can prevent the same history from repeating itself with AI. AV argues that the "abusive" nature of traditional consulting often stems from a lack of "Phase Zero" preparation. Organizations frequently jump into software selection and vendor RFPs without understanding their own internal processes, political buy-in, or desired outcomes. By the time an implementation partner is on-site, the customer has already lost their leverage, leading to endless change orders and "fluffy" risk registers where every red flag is painted green. As we move into the age of AI, AV sees enterprises making the exact same mistakes: chasing shiny "agentic" products before they have established data sovereignty or governance. This conversation serves as a pressure-test for any leader about to sign off on a major digital transformation. AV shares how to reclaim ownership of your data, align consultant incentives with business value, and why the future of consulting belongs to those who can bridge the gap between AI-native thinking and human judgment. Key Takeaways • Success in high-stakes projects is determined before the RFP; spend time documenting processes and securing political buy-in before talking to vendors. • Traditional consulting can become "abusive" when vendors dictate timelines and products based on their own sales targets rather than the client's actual needs. • In the AI era, leaders must ensure they own their data and can move it between third-party tools rather than being locked into a single SaaS provider's ecosystem. • Like ERP, AI adoption fails when it is treated as a product-first purchase instead of a business-process transformation requiring clean data and human oversight. • The traditional billable-hour model is collapsing; value now lies in senior-level judgment, "blameability," and the ability to integrate AI "Lego bricks" into delivery. • While AI can automate the "grunt work" of deliverables, final accountability must always rest with a seasoned human expert who carries the risk of the decision. About AVAV is the CEO of Avero Advisors, a government consulting firm he built from zero to $7.5 million over the last ten years. He's spent two decades helping state and local agencies navigate ERP implementations, AI strategy, and digital transformation, and he's been in the room for a majority of these engagements. He's currently writing a book called Start at Zero and rebuilding his firm around AI agents that handle everything from business development to content production and delivery. Before Avero, AV spent a decade inside the traditional consulting world learning how the machine worked before deciding to build something different. Avero operates as the buyer's agent for government agencies, sitting on their side of the table instead of the vendor's. The firm has grown to a team of around 40 to 50 people, including a Global Innovations Center. Outside of consulting, AV is an active investor. He's invested in BSG Hospitality and Market Square Ventures, applying the same builder's mindset to opportunities outside of govtech. When he's not running the firm or writing, you'll probably find him on a motorcycle. He's an avid rider who uses long rides the same way some people use meditation: to think, decompress, and come back with clarity. AV brings a rare combination to any conversation: deep technical credibility in government technology, real experience bootstrapping and scaling a services business, and an honest willingness to talk about what he got wrong along the way. He's not going to give your listeners a sales pitch. He's going to give them something useful. Chapters00:00 When Consulting Becomes Abusive 08:46 Laying Down the Foundation! 11:43 Ad 12:14 Private Companies vs Private Sectors 16:51 Excited AI Implementation 20:26 AI's Impact 27:09 Ad 27:20 How do You see the Future? 32:29 Starting Out Today! Where to find AV• Website: www.averoadvisors.com • LinkedIn: https://linkedin.com/in/verekar/ • Instagram: https://www.instagram.com/verekar/ • Twitter: https://x.com/AbhijitVerekar AV’s Book https://www.amazon.com/Start-Zero-Leading-Stakes-Modernization/dp/B0GZFQLDJ3

    Your AI Strategy Will Fail for the Same Reason Your Last ERP Did ft. Abhijit Verekar
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About

The CTO Compass is a podcast for CTOs, CIOs, IT directors, and everyone leading technology teams. The hardest part of leading in tech was never the technology. It's leading people, growing into the job while everyone assumes you already know how to do it. That's what this show is about. Every guest brings one lesson: the one thing they'd teach every tech leader, backed by their real stories. The growth, the setbacks, and the decisions that made them the leader they are today. Alongside the interviews, there are solo episodes where Mark shares the leadership lessons from his own career and his executive coaching. This is not a hype show, and it's not theoretical leadership content. Real stories, real mistakes, and lessons you can use. Your host: Mark Wormgoor. He spent 30 years in technology, six of them running global IT teams at JDE, and today he works as an executive coach for IT leaders. If you lead in tech, or you want to, The CTO Compass is built for you.

Information

  • Creator
    Mark Wormgoor
  • Years Active
    2025 - 2026
  • Episodes
    41
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Tairi
  • Show Website
    The CTO Compass