The CTO Compass

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 t...

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...

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 contraria...

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 businesse...

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...

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 wi...

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 i...

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 ca...

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 dig...

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 m...

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 intersecti...

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 initiativ...

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 fi...

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...

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 leade...

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,...

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...

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 fr...

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...

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 infrast...

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...

Hiring has become one of the hardest problems CTOs and CIOs face, and most tech leaders are still using a playbook that no longer works. There is no longer a deep talent pool. Long interview processes lose top candidates. Remote work has changed what “good” looks like. And AI is forcing leaders to rethink experience, roles, and team design entirely. In this episode, Mark Wormgoor speaks with Bill...

Matt Dixon, a seasoned tech leader and fractional CTO, shares insights on aligning technology with business goals, addressing revenue leaks, and the importance of mindset in leadership. He discusses the role of a fractional CTO, the significance of metrics that matter, and the challenges of managing technical debt. Matt emphasizes the need for effective team dynamics and the dangers of shiny objec...

What if the way we talk about tech leadership is completely wrong? In this episode, Telle Whitney - Silicon Valley chip designer turned CEO and co-founder of the Grace Hopper Celebration - joins us to break down the myths that hold technology leadership back. She unpacks the dangerous illusion of meritocracy, the myth of the lone genius, and why many CTOs and CIOs unknowingly lead cultures that si...

In this episode, executive coach and former scale-up CEO Loic Potjes joins us to help CTOs, CIOs, and tech leaders break out of the "busy but stuck" cycle. We explore how to bring strategic clarity to your leadership, define a powerful USP, and position your company for exponential (not just incremental) growth. 🎯 Learn how to: Escape the trap of surface-level innovation Use AI as a strategic co-...