The CTO Compass

Mark Wormgoor speaks with organizational design expert JL Heather about the hidden forces halting innovation and progress in modern tech companies. They dive deep into the concept of "can't culture," an invisible web of structural and cultural barriers that prevents teams from voicing problems, challenging the status quo, and driving meaningful organizational change.Heather explains how omission bias and asymmetrical accountability create environments where employees feel it is far safer to stay silent than to speak up. Rather than trying to force individuals to be braver or crowding meetings with more oversight, executive leaders and CTOs must focus on making dissent cheaper and actively lowering the personal risk of pointing out critical flaws.The conversation offers practical framework tools for business leaders, ranging from running project pre-mortems and assigning devil's advocates to restructuring decision-making meetings. As technology rapidly evolves alongside AI, fostering managerial openness and psychological safety becomes essential for software engineering teams and enterprise leadership alike.Key Takeaways• Leaders must reward early warning signs to rebalance an environment where staying quiet carries zero career risk.• Focus on lowering the personal cost of speaking up rather than forcing individuals to be braver or adding more oversight.• Real behavioral change requires removing rigid structural approval barriers alongside driving cultural initiatives.• Break consensus bias by assigning devil's advocates, running project premortems, and having senior leaders speak last.• Build psychological safety by soliciting unprompted input, taking visible action on feedback, and protecting messengers.• Treat reported problems as valuable assets so teams feel safe raising red flags before minor issues turn catastrophic.• Define clear overall destinations so teams focus on removing obstacles to deliver business value rather than rigidly following process.Chapters00:00 Can't Culture04:08 Spotting Real Constraints09:57 Ad10:13 Getting People to Speak15:56 Changing the Culture21:38 Ad22:19 The Software/Engineering Side24:31 Can't Culture Around AI28:20 You're Own Team's Can't Culture31:02 What to Actually Do About itWhere to find JLWebsite: https://centered.work/LinkedIn: https://www.linkedin.com/in/jlheather/YouTube: https://www.youtube.com/@BreakthroughInnovationMy Socials• Website: https://tairi.co• LinkedIn: https://www.linkedin.com/in/mwormgoor• Instagram: https://www.instagram.com/markwormgoorContact Us• Business Email: [email protected]

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 Crises09:34 Ad10:07 You're Skills Matter!13:07 AI as a Partner, Not a Replacement15:41 Fear of Change19:22 Ad19:34 Helping People Through Change22:12 Kindness Through Fear23:51 Falling In Love with Your Idea26:59 The Sticky Note Exercise28:43 Unleashing InfluenceWhere to find Angela• Website: http://app.unleashinginfluence.com/v3• LinkedIn: https://www.linkedin.com/in/angelamulrooney

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 202608:56 Utilizing Your Time!13:32 Ad14:04 The Truth about AI Agents16:22 Handling Multiple Teams17:56 Keeping Up With Modern Technology!23:01 What Skill Should You Develop?28:10 Ad28:21 The Future of Engineering Managers32:04 Growing in ComplexityWhere to find Alex• LinkedIn: https://www.linkedin.com/in/alexponomarev/

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 Curiosity07:56 Keeping Up with Technology10:07 The Contrarian's Mindset13:51 Ad14:22 Surviving 17 Years!18:24 Biggest Mistakes and Small Ws24:42 Long Term Professional Relationships27:48 Ad28:00 Tech Market Cross Section!37:12 Agents, Assistants, and Reviewers44:32 Working With Your TeamWhere to Find Dominic• Website: https://domandtom.com/• LinkedIn: https://linkedin.com/in/domtancredi

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 TakeawaysThe 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 Approach05:53 gptstudio and workilo13:15 Ad13:47 AI Adoption Fear16:41 gptstudio's Userbase18:55 Ad19:06 Servers and AI Agents25:08 AI Platform Locking27:50 Teaching in the Age of AI31:08 What's Next?Where to find Clive• Website: https://gptstudio.workilo.io/• LinkedIn: https://linkedin.com/in/clivemoore• Instagram: https://instagram.com/clivemoore1979

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 Technology13:51 Ad14:21 Cybersecurity In The Age of AI16:12 Panic Selling vs Panic Buying22:36 Applying AI in Today's Market29:04 Ad29:15 The Problem With Vibe Coding33:29 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

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 Ad12:27 23 Years of Growth and Change15:41 The Value of People19:51 Customization Accommodation26:44 Ad26:55 Who Makes Technology Decisions?28:25 AI Implementation and AI Policy Issues36:36 The Future of TechWhere to find MikeWebsite: https://www.teamtectonic.com/LinkedIn: https://www.linkedin.com/in/miketoguchi/

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 Leadership06:33 Getting Promoted14:39 Ad15:11 What are You Busy With?20:26 How to Give Feedback22:53 Female Engineers!24:50 Coaching The Executives29:08 Ad29:19 Getting Unstuck36:54 Working with Different People40:45 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

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 Abusive08:46 Laying Down the Foundation!11:43 Ad12:14 Private Companies vs Private Sectors16:51 Excited AI Implementation20:26 AI's Impact27:09 Ad27:20 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/AbhijitVerekarAV’s Bookhttps://www.amazon.com/Start-Zero-Leading-Stakes-Modernization/dp/B0GZFQLDJ3

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 Management07:26 What Kills Great Ideas?14:05 Aligning Individual Self-Interests17:25 Ad17:56 The Reality of Reorganization27:35 Unexpected Transformation31:02 Looking for Change!34:50 Ad35:00 Team Capacity vs Company Demand40:30 CTOs Have Power!47:06 Organizational CynicismWhere to find Bud• Website: https://nobl.io• LinkedIn: https://www.linkedin.com/in/budcaddell

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 assumptionsAbout 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 Journey05:42 Treating People as Machines12:38 AI's Societal Impact12:06 Ad20:32 What is Your Responsibility?26:00 What is Homo Conexus?39:01 Ad38:12 The Ugly Phase of Transformation42:25 A Hopeful Perspective!Where to find Margôt• Website: https://margotvanbrakel.com• LinkedIn: https://www.linkedin.com/in/margotvanbrakel/• Instagram: https://www.instagram.com/margotvanbrakel/

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 Owner05:47 Launching DOWN12:54 Ad13:26 The Controversial "Bang With Friends"17:42 "Outrageous Startup Growth"24:18 Ad24:29 Psychology as a Foundation!28:14 Standing Out Through The AI Noise30:10 Past Advice and Future Plans!33:22 Behavioral Improvement and Empathetic ApproachAbout 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

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 adoptionAbout 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 Assumption09:37 Why Pragmatic Solutions aren't Enough15:08 Ad15:40 How Important is Compliance?22:29 When Does the Problem Start?28:59 Working with Enterprise Organizations34:17 Dealing with Compliance Complexity39:07 Ad39:19 Expensive Integration Mistakes46:26 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

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 outcomesAbout 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 Ad07:28 Working in Nigerian Financial Technology13:35 Fraud, Features, and Leadership22:51 Ad23:03 Complicated Solutions and Inspiration26:38 The Future of Circle Funds29:46 Mentorship Experience31:05 You Need a Community!Where to find ErioluwaWebsite: https://circlefunds.ioLinkedIn: https://www.linkedin.com/in/asiru-erioluwa/

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 systemsAbout 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 Failures05:26 Reliability of AI Models11:24 Ad11:57 "AI for the Rest of Us"16:28 Starting With AI24:54 Explaining AI to the Board27:37 Ad27:48 AI Unrealistic Expectations32:42 What kind of People does AI Demand?36:49 Keeping Up with AI39:15 AI PredictionsWhere 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/

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 TakeawaysWhy 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 mistakesAbout 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 Truth04:38 AI's Hidden Consequences (NIST)12:47 Ad13:19 Approaching AI as a CTO18:45 FOMO in the Corporate World22:57 Keeping Up with AI28:42 Ad28:53 Effectively Using AI37:27 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

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 oversightRather 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 modelsIf 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 TakeawaysWhy 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 assumeAbout 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 Output20:54 Dealing with Bad Actors (Human or AI)25:36 Approaching AI as a Small Scale CTO30:43 Democracy of AI Agents35:15 AI Safety Conferences40:03 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

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 economyAbout 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 Perspective06:06 Avatar Buddy14:04 Automation using AI24:47 Getting People Into AI31:05 Working with Smaller Systems35:16 C-level People and Personal Growth43:42 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-MEeQMy Socials• Website: https://tairi.co• LinkedIn: https://www.linkedin.com/in/mwormgoor• Instagram: https://www.instagram.com/markwormgoorContact Us• Business Email: [email protected]

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 environmentsAbout 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 CTO05:48 "I need to fix everything"10:56 Delivery Expectations and Overwork21:54 What Burnout Looks Like26:40 When Standard Training Isn't Working33:05 Bringing People into the Culture37:54 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/markwormgoorContact Us• Business Email: [email protected]

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 CIOsWhy 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 AIAbout 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 Direction07:44 What is Data Readiness in AI?12:49 Where Do You Start with AI Data?17:43 AI Implementation in Your Business26:11 Microsoft Copilot is Overtaking!37:04 AI Enterprise Adoption43:53 Leveraging AI for Big ChangesWhere 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/markwormgoorContact Us• Business Email: [email protected]

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 projectChapters00:00 Handling Business Overload07:09 Simplifying the Process14:47 The Hurdles of Implementation18:31 Problems with Old Contracts23:11 OpenAI's Strict Timeline25:54 Complexity under Simplicity31:26 Implementing AI35:40 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

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 exitChapters00:00 When the Leader is the Bottleneck07:58 Being Open to Change15:36 Handling Visionaries19:12 How to Approach Delegation26:27 AI in Today's Business Landscape37:14 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

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 Kasko, President and CEO of Frontline Source Group, a national staffing and executive search firm. Bill began his career in IT security and infrastructure before spending more than 20 years helping companies hire and scale teams, giving him an expert view of what actually works in today’s market.You’ll learn:Why there is no longer a true “talent pool”, and how to hire without oneHow to design tech roles around outcomes instead of outdated requirementsWhere great tech talent actually comes from todayHow remote work has changed hiring signals and expectationsWhy adaptability matters more than years of experience in the AI eraThe one leadership habit that consistently separates strong tech teams from weak onesIf you’re a CTO, CIO, or senior tech leader and you frequently need to hire, this episode will help you rethink how you build teams.Chapters00:00 Starting Out in IT08:29 Infrastructure and Security Today15:46 Where To Start With Recruitment24:34 What's The Secret with Recruitment30:50 Approaching Remote Work36:56 The Hiring IT Landscape42:33 Hiring In Today's Market46:52 Hiring Retention50:26 Communication is Important!About BillBill Kasko is a seasoned business leader and entrepreneur with extensive experience in strategic planning, business development, and organizational growth. With a proven track record of driving results across multiple industries, Bill brings valuable insights into leadership, innovation, and sustainable business practices.Where to find Bill• Website: https://www.frontlinesourcegroup.com• LinkedIn: https://www.linkedin.com/in/billkasko/• Instagram: https://instagram.com/frtline• YouTube: https://www.youtube.com/@frontlinesource

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 object syndrome in tech. He also explores the future of AI in business and the evolving role of CTOs in modern organizations.Chapters00:00 Tech, Business, and Leadership04:16 Revenue Leaks and Fractional CTO Work08:41 Working with Existing Tech Teams13:02 Managing Expectations and Misunderstandings16:39 Code Program and Misaligned Priorities20:58 Technical Debt and Shiny Object Syndrome26:47 What CTO's Should Be Doing28:55 AI in Tech and BusinessAbout MattMatt Dixon is the Founder and CEO of Front Range Systems, serving as a Fractional CTO for growth-stage companies generating $10-75 million in revenue. With over 25 years of technology leadership experience, Matt specializes in identifying and eliminating "revenue leaks": the invisible operational inefficiencies that cost companies significant money through manual processes and misaligned systems.Now based in Nashville, Matt focuses on logistics, insurance, healthcare, and sports industries, delivering operational clarity and measurable cost reductions within 90 days.When he's not helping CEOs fix their operations, you'll find him on track days pushing limits behind the wheel or traveling with his wife.Where to find Matt• Website: https://frontrangesystems.com/• LinkedIn: https://www.linkedin.com/in/mattdixon/• Instagram: https://www.instagram.com/fractionalctomatt• YouTube: https://www.youtube.com/@FractionalCTOMatt

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 silence key voices. Drawing from her book Rebooting Tech Culture, Telle offers actionable insights for building inclusive, creative, and high-impact organizations, starting at the executive and board level.Listen to learn how today’s tech leaders can:Rethink hiring and strategy for real boardroom impactBuild cultures that amplify innovation (not just output)Spot the hidden signals that sabotage diversity and creativityLead with courage, even when you feel like an imposterChapters00:00 From Theater to Computer Science05:39 The Grace Hopper Celebration11:27 Rebooting Tech Culture20:12 Meritocracy and The Lone Genius26:15 What a Company actually needs32:44 Does Inclusivity Improve The Output?34:28 AI4ALL38:43 Taking RisksAbout TelleTelle Whitney is a consultant, senior executive leader, and recognized expert and advocate for diversity and women in technology. Telle has been called "a pioneer for the promotion of women technologists" and was named one of Fast Company's Most Influential Women in Technology. Telle served as CEO of the Anita Borg Institute from 2002 to 2017 and cofounded the Grace Hopper Celebration of Women in Computing conference. Prior to joining the Anita Borg Institute, she was vice president of engineering for Malleable Technologies. She holds a PhD in computer science and is now a speaker and consultant helping executives and their companies create cultures where diverse teams thrive.Where to find TelleTelle Whitney's book: Rebooting Tech Culture: How to Ignite Innovation and Build Organizations Where Everyone Can ThriveWebsite: https://www.tellewhitney.com/LinkedIn: https://www.linkedin.com/in/telle-whitney/

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 innovationUse AI as a strategic co-pilot, not a tactical bolt-onTransform from technical expert to strategic leaderLead with clarity, purpose, and structure, especially in fast-scaling environmentsChapters00:00 Worldwide CEO Experience Perspective06:23 Transitioning for the Future11:30 Personal Growth as a CEO14:07 Business-Tech Mistakes21:52 Change and Improvement29:22 Coaching Growth34:49 Business AI Integration41:50 Navigating the AI Hype48:10 Simplifying Your PitchAbout LoicLoic has a global perspective and 25 years of experience as a corporate/scale-up CEO, chairman and tech investor, and therefore uniquely qualified to partner with CEOs across diverse industries and growth stages. He has successfully launched, structured, and grown companies across mature and emerging markets, managing up to 4,000 employees at a time, with core expertise in go-to-market strategies, new technologies, innovation, and mergers & acquisitions.Where to find Loic• Website: https://www.disruptiveleap.com• LinkedIn: https://www.linkedin.com/in/loicpotjes/

Hollis discusses the intricacies of raising capital, emphasizing the importance of multiple interactions with potential investors. He highlights the average of 32 touchpoints required to secure a significant investment and explores how AI can streamline this process without compromising the quality of engagement.Chapters00:00 Beginnings with Technology and Career06:20 When to use Tech and People08:08 Implementing Tech into Real Estate (Raise AI)12:45 Streamlining "32 Touch points" with AI19:31 Building a Team and AI Adoption24:06 AI Future-proofing and Relationships28:36 Why Real Estate AI and Building Culture33:02 The Future of Raise AIAbout HollisWilliam Hollis, known as “Hollis,” is the Founder & CEO of Raise AI, where he helps real estate capital raisers and fund managers use AI-powered automation to streamline investor communication, increase deal visibility, and raise capital faster. A self-taught software engineer turned real estate investor, Hollis specializes in bridging cutting-edge AI technology with the real-world challenges of capital raising.Born and raised in Hollis, Queens, NY, he has built his career at the intersection of AI, automation, and real estate. Before founding Raise AI, Hollis developed AI solutions for global brands like Disney and Nike, then applied those same efficiencies to real estate by launching 24 Capital Group in 2022 and 24 Tech Systems in 2024. Today, through Raise AI, he empowers dealmakers with scalable, intelligent systems that replace manual follow-ups and outdated workflows—helping them move from hustling for capital to raising it effortlessly.Where to find Hollis• RaiseAI: https://theraiseai.com/• Website: https://williamhollis.com/• LinkedIn: https://www.linkedin.com/in/rei-hollis/

Scott Morris, a veteran HR leader turned startup founder, discusses his transition from a successful corporate career to launching Propulsion AI, an innovative company focused on AI-powered HR solutions. He highlights the significant challenges in traditional HR practices, particularly the lack of clarity in role expectations and the misalignment of employee engagement. Scott introduces Athena, an AI teammate designed to enhance role design and improve hiring processes, ultimately aiming to create a more effective and engaged workforce. The discussion also touches on the future of hiring, performance management, and the importance of understanding the value of operational roles within organizations.Chapters00:00 - Risks, Startups, and HR07:35 - Solving The Problem with Hiring14:39 - Athena and Propulsion21:20 - Importance of Operational Roles25:04 - Athena as a Teammate29:41 - Collaborating with Tech32:08 - Culture in the Hiring Process34:32 - Are You Ready to Hire?38:41 - Future of HR Tech41:44 - Hiring and Managing AdviceAbout ScottWith more than 25 years of HR leadership - including two decades at the C-suite level - Scott Morris has navigated talent management across five distinct industries and two continents. He's led HR strategy for nimble tech startups with 250 employees and orchestrated comprehensive workforce solutions for enterprises exceeding 15,000 employees. His experience spans the full spectrum of organizational complexity, guided by a core philosophy: if it feels comfortable, you're behind.Scott is now Founder & CEO of PropulsionAI, building the first HR team made entirely of AI - digital teammates that coach managers through strategic talent decisions using proven frameworks. These AI coaches clarify how roles connect to business outcomes, transform hiring and performance management, automate labor-intensive documentation, and help organizations simultaneously raise employee engagement and productivity.Where to find Scott• Website: https://getpropulsion.ai/• LinkedIn: https://www.linkedin.com/in/mscottm/

Mark and Margaret explore how leaders can operate effectively in unpredictable environments, emphasizing curiosity, reflection, and making decisions without perfect information. They discuss the limits of efficiency, the risks of relying too heavily on metrics, and how AI may weaken independent thinking. Margaret shares real examples of leaders who improved their organizations by listening more, empowering their teams, and building trust. They also examine extreme work cultures, the importance of maintaining personal autonomy, and how strong social connections in remote teams support better collaboration and problem-solving.Chapters00:00 - The World of Uncertainty03:57 - Curiosity in Business10:15 - Measurements, Data, and KPIs12:51 - Letting AI think for Us16:29 - Growing Leadership Skills26:31 - CEO Coaching Experience33:29 - 9-9-6 Mentality38:00 - Business Trends40:00 - Social Capital with Global Teams45:40 - Margaret's Essential QuestionAbout MargaretDr. Margaret Heffernan began her career producing BBC radio and television programmes, including dramas, documentaries, and the first broadcasts featuring Simon Schama. After moving to the United States, she led multimedia initiatives for Intuit, The Learning Company, and Standard & Poor’s, later serving as CEO of InfoMation Corporation, ZineZone, and iCast. Recognized as one of Streaming Media’s “Top 25” and The Hollywood Reporter’s “Top 100 Media Executives,” she is also the author of seven influential books, including Willful Blindness, A Bigger Prize, and the best-selling Uncharted. Her TED talks have been viewed more than fifteen million times, and her next book, Embracing Uncertainty, will be published in 2025.A Professor of Practice at the University of Bath, Heffernan mentors global CEOs through Merryck & Co., speaks at major international conferences, and chairs the board of DACS. She has advised high-profile public inquiries, was inducted into the Thinkers50 Hall of Fame in 2023, and is a frequent BBC Radio 4 broadcaster. She also writes for the Financial Times and serves as a parish councillor.Where to find Margaret• Website: https://mheffernan.com/• X: https://x.com/M_Heffernan• Ted: https://www.ted.com/speakers/margaret_heffernan• Substack: https://heffernanm.substack.com/

David Soileau discusses the potential of AI and automation in optimizing customer service and order processing. He emphasizes the importance of accurate order entry to reduce the need for customer service interactions and highlights the benefits of automating documentation processes. The discussion also touches on the shift towards self-service options, reducing manual data entry, and streamlining operations to enhance efficiency.Chapters00:00 – Gopher’s Origin & Pivot04:18 – Why Logistics Needs Tech07:40 – Going Digital in Old Industries10:16 – AI Features: Pic-to-Ship & GoPilot12:12 – Tech Challenges & Early Mistakes16:21 – Team, CTO, and Automation20:07 – Fixing Legacy Logistics24:23 – Techstars, Expansion & Future of AIAbout DavidDavid is an entrepreneur and founder passionate about building companies that transform industries and create lasting impact. As a Co-founder of Gophr, he's part of a team redefining logistics and procurement. By combining pricing intelligence, technology, and service, they’re delivering a faster, smarter, and more cost-effective way for industrial and construction businesses to move materials and products. Their vision is to save teams time, reduce costs, and reshape the future of logistics. He's also a founder of Embark, a business incubator designed to launch and scale ventures that matter. At Embark, they provide entrepreneurs with the tools, network, and mentorship needed to transform ideas into thriving businesses. Alongside these ventures, David owns Integrity Homes, a residential construction company built on trust, craftsmanship, and long-term relationships. Whether it’s homes, logistics systems, or startups, his passion is taking ideas from the ground up and scaling them into businesses that create real impact. David thrives on solving big problems, building strong teams, and driving sustainable growth. Always open to connecting with leaders, innovators, and partners who share a vision for building what’s next.Where to find David• Website: https://gophrapp.com/• LinkedIn: https://www.linkedin.com/in/davidtheguy• Youtube: https://youtube.com/@gophrapp

How do you lead when AI is changing everything about how we work? Mike Todasco, former Senior Director of Innovation at PayPal and Visiting Fellow at the SDSU AI Lab, talks about what it really takes to build an AI-first organization. Mike shares hard-won lessons from running innovation inside Paypal, why most teams get stuck in “pilot hell,” and how leaders can build a culture that embraces experimentation instead of fearing it.Mark and Mike also explore the human side of tech leadership: creativity, curiosity, adaptability, and how to stay grounded as AI accelerates. From PayPal’s innovation tournaments to the future of work and the rise of solopreneurs augmented by AI, this episode gives CTOs and tech leaders a clear, practical view of what’s coming, and how to prepare.Chapters00:00 Who Is Mike Todasco? 02:42 What AI-First Really Means for Companies 04:32 How Leaders Can Drive AI Adoption 07:56 Inside PayPal’s Innovation Culture 15:31 Getting Executive Buy-In for Innovation 21:06 The Leadership Skills That Matter in the AI Era 32:42 The Future of Work: Humans + AI 39:43 When AI Feels Overwhelming (Mike’s Advice) About MichaelMichael Todasco is the former Senior Director of Innovation at PayPal, where he spent over a decade leading initiatives to design, test, and scale disruptive ideas across the company. He is currently a Visiting Fellow at San Diego State University’s Artificial Intelligence Lab, where he explores the intersection of AI, creativity, and the future of work. In addition, he is pursuing his MFA in Creative Writing at Johns Hopkins University, blending his passion for storytelling with his expertise in technology. A frequent speaker and writer on AI, innovation, and creativity, Michael helps audiences rethink how to stay relevant and human in a rapidly changing world.Books Referenced• "How to Win Friends and Influence People" by Dale CarnegieWhere to find Michael• LinkedIn: https://www.linkedin.com/in/todasco/• Website: https://todasco.lovable.app/

Coby Skonord founded IdeaWake, an innovation crowdsourcing platform. He addresses common misconceptions about innovation in organizations, the role of technology leaders, and the importance of integrating innovation into company culture. Koby also shares insights on overcoming budget constraints, navigating security challenges, and the impact of AI on innovation processes. He emphasizes the need for a sustainable innovation culture that is measured and integrated into the organization's goals.Timestamps00:00 – Leaving EY to Build Ideawake02:35 - Why Innovation Fails Inside Big Organizations03:47 - Building a Culture That Enables Innovation05:26 - Turning Ideas into Impact09:38 - Innovation in Healthcare and Regulated Industries10:37 - The CTO’s Role in Driving Innovation13:50 - Escaping the Budget Trap19:35 - Breaking Through Enterprise Barriers26:36 - The Future of Innovation and the Role of AIAbout CobyCoby Skonord helps corporate innovation, improvement, and HR teams more effectively tap into the wisdom of employee ideas.Over the last decade he's led the team at Ideawake, an innovation management platform used by thousands of companies like KraftHeinz, SiriusXM, and Jason's Deli power their employee ideas program focused on growing revenue, reducing costs, and improving efficiency.Where to find Coby• Website: https://ideawake.com/• LinkedIn: https://www.linkedin.com/in/coby-skonord/

Bart Spangenberg, co-founder and CTO of NewU, shares his personal health journey and how it led him to create a health tech company focused on employee well-being. He discusses the challenges of transitioning from a health background to tech, the importance of data privacy in health apps, and how behavioral science informs the design of their application. Bart also highlights the significance of building a strong remote team, hiring for culture, and the future goals of New You, including market expansion and integrating their services into organizations.Timestamps00:00 From Personal Struggles to a Mission in Health02:49 Learning to Code & Building NewU06:39 Lessons from Working with an Agency08:49 What NewU does10:59 Privacy by Design and Trust in Health Data14:19 Digitizing the Dutch PMO: Compliance Meets Health15:50 Leading a Remote International Development Team20:04 Hiring for Mindset, Growth, and Culture Fit26:29 Applying Behavioral Science to Product Design32:36 The One Thing: Focus and Decision-Making in LeadershipAbout BartHealth, you wish the best for your friends and family. However, sometimes we forget to take care of ourselves. That was me. Ignited by being not so healthy, I decided to turn things around. Health has fascinated me for many years now. This wonderful obsession has greatly improved my life, and I hope it will make yours phenomenal as well!My mission is to help as many people as possible to take control of their health.I found that this is achieved best through digital solutions. So NewU was born. Our enterprise builds digital health solutions for exercise, nutrition, sleep, connectedness, smoking, mental wellness and much more. Every day I am grateful that I can work with passionate professionals that share this mission.You can wake me up to talk about technology, behaviour, UI/UX, high performance, design, habits or health.Books referenced• Designing for Behavior Change by Stephen Wendel• The Phoenix Project by Gene Kim, Kevin Behr & George Spafford• Clean Code by Robert C. Martin• Clean Architecture by Robert C. Martin• The Pragmatic Programmer by Andrew Hunt & David Thomas• The One Thing by Gary Keller & Jay PapasanWhere to find Bart• Website: https://www.newu-app.io• LinkedIn: https://www.linkedin.com/in/bartspangenberg/

Peadar Coyle, CTO and co-founder of AudioStack, shares insights on building an AI-driven audio production company before the AI hype. He discusses the importance of understanding customer needs, the impact of AI on workflows, and the significance of team dynamics in a distributed environment. Coyle also emphasizes the value of open source contributions and offers advice for startup founders navigating the competitive landscape of AI technology.Timestamps00:00 Building AI Before the Hype03:41 Surviving the GPT wave05:57 Defensibility without mega-rounds07:30 What AudioStack actually does08:11 One-to-many: turning unscalable into scalable12:06 Thin wrappers vs thick platforms14:58 Model churn & provider neutrality19:34 Ship faster: the metric that matters24:17 Open Source Communities vs. Business Customers26:40 Scaling across locations30:25 Government advice36:05 CTO and Startup LessonsAbout PeadarPeadar Coyle is CTO and co-founder of AudioStack.Together with the Head of Engineering, he is dedicated to making AudioStack’s audio production infrastructure flexible, reliable, secure and scalable to meet the diverse ambitions of agencies, brands, publishers and AdTech.He is an authority on software engineering, data science and AI, and has been invited on multiple occasions as a contributor to steering groups on AI innovation by industry groups and the UK Government.He has long been an involved member of the Open Source community, and his core role in developing PyMC3, a Bayesian Computing Library, has supported the development of numerous scaleups around the world.With an AI-native, technical founder’s perspective, he is passionately involved in conversations about the culture of engineering and has published a series of interviews of the teams behind data science innovations at some of the world’s best-known tech disruptors (Amazon, Spotify, Etsy).Where to find PeadarAudiostack Website: http://www.audiostack.ai/Peader's LinkedIn: https://www.linkedin.com/in/peadarcoyle/and on Youtube: https://www.youtube.com/c/Aflorithmic

In this conversation, Tony Kyriakidis, founder of Nevron, shares his journey from Cyprus to the Netherlands, detailing his experiences in software development and the establishment of Mission Control, a platform for incident management. He discusses the importance of learning the local language for business success, navigating government contracts, and transitioning from an agency model to a product-focused company. The conversation also explores the role of AI in incident management, proactive project management strategies, and the freedom and challenges of entrepreneurship.Timestamps00:00 Introduction 02:19 Learning Dutch & Fitting in10:16 Landing the First Government Client15:27 Transitioning from Agency to Product19:45 What Mission Control actually does24:36 Leadership & Operations at Scale33:36 AI in Incident Management38:51 Risk Planning & Entrepreneurial Mindset42:16 Freedom and EntrepreneurshipAbout TonyTony is the founder of Nevron B.V., a software company specialized in mission-critical systems for governments, law enforcement, organisations, and major events. Since starting his entrepreneurial journey with Smashing Parties in 2014 and Venuepark in 2016, he has built a track record of delivering high-impact solutions. Under his leadership, Nevron’s software has been used during the Formula 1 Dutch Grand Prix, by the Dutch National Police, Rijkswaterstaat, and at leading festivals in the Netherlands. With a clear mission to become the world’s leading incident and operations management software company within the next 30 years, Tony continues to drive Nevron forward.Where to find TonyWebsite: https://nevron.ioLinkedIn: https://www.linkedin.com/in/tony-kyriakidisInstagram: https://instagram.com/iam.tony

Nola Simon is a strategic futurist, and we discuss the evolving landscape of remote work, the importance of trust and connection in the workplace, and the integration of AI with her. Nola shares her insights on building engaged remote teams, the significance of asynchronous work, and the necessity of measuring trust within organizations. She emphasizes the need for strategic foresight in navigating rapid changes in technology and society, and discusses the role of narrative intelligence in leadership. The conversation concludes with practical advice for CTOs on fostering a culture of trust and engagement in distributed teams.Chapters00:00 Intro to Remote Work & Flexibility05:34 Creating Connection in Remote Teams10:55 Async workflows, documentation, and AI13:31 Earning trust for knowledge sharing15:16 Measuring trust via outcomes & psychological safety29:04 Strategic foresight: scenarios and adaptability in AI turbulence44:35 Playbook for first-time distributed CTOsAbout NolaNola Simon is a strategic futurist and a steady voice for leaders navigating the messy, human moments at work. Her keynotes are part mirror, part map—reflective, insightful, and grounded in the lived experience of leading when the future isn’t clear.What sets Nola apart? She blends sharp systems thinking with a warm sense of humour and a love of pop culture. Whether it’s a tongue-in-cheek reference to a classic sitcom, a playful callback to a viral meme, or a story about the unexpected lessons of a Zoom mishap, Nola uses levity to spark connection and make big ideas stick. Her sessions are as likely to include a laugh-out-loud anecdote as a breakthrough leadership insight.As host of Hope & Possibilities: A Love Letter to the Future of Work, Nola brings lived experience, quiet power, and a knack for making people smile to every stage. She adapts to the moment—remote, hybrid, or in person—always with clarity, presence, and deep respect for the space she’s in.Nola invites audiences to question assumptions, explore new perspectives, and leave with a renewed sense of agency, possibility, and optimism about the future of work.Where to find Nola• LinkedIn: https://www.linkedin.com/in/nolasimon• Youtube: https://youtube.com/@nolasimonsayings• Website: https://www.nolasimon.com

In this episode of the CTO Compass podcast, Mark interviews Kelsey Daingerfield, founder of Pocket COO, who specializes in bridging the gap between technical teams and executive leadership. Kelsey shares her journey from higher education to entrepreneurship, discussing the importance of the visionary vs. integrator dynamic, the role of a fractional COO, and how to identify operational red flags. She emphasizes the significance of effective delegation, change management, and communication within teams, as well as the need to change the perception of IT departments. Kelsey also highlights the potential of AI in optimizing operations and shares a success story of transforming a business to achieve greater efficiency and work-life balance.Chapters00:00 Introduction & Background02:13 Visionary vs. Integrator (Rocket Fuel)05:00 Transition into Entrepreneurship08:24 Client Work Examples11:28 Recognizing Operational Red Flags18:39 Delegation & Leadership Challenges25:33 Change Management & Communication31:15 AI in Operations37:42 Common Leadership Pitfalls40:14 Success Story43:23 Final Advice & Wrap-upAbout KelseyKelsey Daingerfield is the founder of The Pocket COO, where she partners with growth-stage founders to help them scale without burnout. With a background in operations, marketing, and project management—plus early career experience working alongside engineers—Kelsey is a master of translating vision into execution and bridging the gap between technical teams and executive leadership.Today, she serves as a strategic COO and advisor for founders who are scaling fast but feel stuck in the weeds. Her specialty is turning chaos into clarity by building the operational infrastructure businesses need to run smoothly and sustainably. Whether it’s team delegation, systems setup, or change management, Kelsey brings both structure and soul to her clients’ companies—so they can grow without grinding themselves into the ground.Where to find KelseyWebsite: https://www.kelseydaingerfield.com/LinkedIn: https://www.linkedin.com/in/kelseydaingerfield/Instagram: https://www.instagram.com/kelseydaingerfield/

In this episode Ahmed Bashir, head of engineering at DevRev shares his journey from Apple to DevRev, discussing the excitement of reimagining work through AI and the importance of writing in the age of technology. He explains how DevRev integrates AI from day one, the significance of knowledge graphs and vector databases, and shares customer success stories. Ahmed also delves into managing a global engineering team, his leadership philosophy, and the impact of AI tools on software development. The conversation concludes with insights on the future of AI and its influence on the younger generation.Chapters00:00 Going from Apple to DevRev08:13 Built-In AI: How DevRev Differs from Other Platforms15:44 Writing as a Superpower in the Age of AI22:10 Knowledge Graphs vs. Vector Databases25:22 Using AI to enhance Work Observability35:43 Leading Remote Engineering Teams at Scale41:57 How an AI company uses AI tools in Software Development46:48 The Future of AIAbout AhmedAhmed Bashir is Head of Engineering at DevRev, where he leads global engineering and promotes a culture of clarity, writing, and outcome-driven work. Previously, he was Director of Engineering at Apple, building large-scale cloud infrastructure. He began his career at IBM Research, working on DB2 optimization. He holds B.S. and M.S. degrees in Computer Science from UT Dallas, pursued a Ph.D. at UIUC, and attended Stanford. His immigrant background and early work experiences shaped his values of humility, curiosity, and inclusive leadership.Where to find AhmedDevRev: https://devrev.ai/LinkedIn: https://www.linkedin.com/in/ahmedmbashir/

In this episode, Zulfiya Forsythe, CEO and founder of the Omadli Group, shares her journey from accounting to the tech industry. She talks about the importance of automation and AI in optimizing business processes. She discusses her experiences in building her company during the COVID pandemic, the innovations in AI agents for businesses, and the misconceptions surrounding AI in the corporate world. Zulfiya also highlights the skills needed for tech leaders in the evolving landscape of AI and shares valuable lessons learned in her entrepreneurial journey.Chapters00:00 Introduction08:36 The Role of AI in Data Management10:26 Launching a Business during COVID18:05 Client Impact Stories22:35 AI in Construction and Plumbing31:30 Financial Impact of AI38:51 Skills for Tech Leaders in the AI Era44:07 Lessons LearnedAbout ZulfiyaIt all started with a simple question: “There has to be a better way, right?”Zulfiya began her career in accounting, spending countless hours buried in spreadsheets. The inefficiencies were frustrating, and she knew there had to be a smarter way. That curiosity led her to discover automation and data analytics, starting with Visual Basic and SQL. The first time she watched millions of data rows transform in seconds, she was hooked.That passion pushed her to transition into the world of data, where she deep-dived into data analytics and automation. Fast forward to today, she is the CEO and Founder of Omadli Group, where they help businesses streamline operations, uncover valuable insights, and use AI to buy back their time. Additionally, she offers AI coaching to help individuals and organizations unlock the full potential of artificial intelligence in their work. Her mission is simple: turn complexity into simplicity and empower businesses to focus on what truly matters.Where to Find ZulfiyaWebsite: https://omadligroup.com/Youtube: https://www.youtube.com/@zulfiyaforsytheInstagram: https://www.instagram.com/zulfiyaforsythe/LinkedIn: https://www.linkedin.com/in/zulfiya-forsythe-akbarova-cpa-0214b98

In this episode, Mattia Peiretti shares his journey from a young tinkerer to the CTO of PocketCFO, a startup focused on making finance effortless for entrepreneurs. He discusses the importance of curiosity, the role of AI in finance, and the dynamics of building a successful team. Matt emphasizes the need for daring and innovation in the tech landscape, offering valuable insights for aspiring CTOs and entrepreneurs.Chapters00:46 Intro & Early Tech Obsession05:04 From School Projects to Running an Agency12:10 Scaling Up at Pararius16:17 Inside the Antler Experience22:58 Finding a Co-Founder & PocketCFO’s Start29:32 Why SMEs Matter & The Future of Finance41:00 Building Fast, Smart Tech without Regrets50:42 Lessons & Advice for Aspiring CTOsAbout MattiaMattia is a techie at heart. Since the age of 3 years old he was fascinated with technology and the impact that could be achieved by it. From taking toys apart and playing with Arduino at 10, to building a game engine in C++ at 12, to starting a Web dev and Marketing agency at 18.His passion for building also expanded from tech to business. Building innovative products that solve real world problems. Having worked with lots of SMEs and having seen their problems up close, now on a mission to make finance for SMEs intuitive and proactive, leveraging AI and cutting egde technologies.Where to find MattiaLinkedIn: https://www.linkedin.com/in/mattiapeiretti/Website: https://mattiapeiretti.com/PocketCFO: https://pocketcfo.io/

In this conversation, Niranjan Sridhar shares his extensive journey in technology and transformation leadership, emphasizing the importance of curiosity, change, and impact. He discusses pivotal moments in his career, the significance of co-creating experiences for the future, and the challenges of leading large-scale transformations. Niranjan also highlights the critical role of change management, the need for trust within teams, and the evolving landscape of AI in business. He offers valuable insights for aspiring leaders, stressing the importance of authenticity and the journey over the destination.Chapters00:00 Introduction to Niranjan 04:50 Pivotal Moments and Decisions in Career08:58 The Philosophy of Co-Creation and Three Foundry13:45 Success Factors in Large Transformation Programs22:42 Transitioning from Program Director to CIO26:11 Transforming Business Processes: The Lipton Case Study31:19 Navigating the AI Landscape: Learning and Implementation39:19 Adapting to Rapid Technological Change: The Future of Business Programs43:15 Lessons from Setbacks: The Importance of Change Management47:59 Leadership Insights: Authenticity and Continuous LearningAbout NiranjanBorn in India and raised by the World, Niranjan is a strategic, outcome-driven, CIO & transformation leader with >25 years of experience delivering technology enabled value creation across PE-backed enterprises, consumer goods, and global consulting. He is a purpose led, people focused, practical & pragmatic leader grounded in the core values of integrity, respect, excellence. He has lived in 5 continents, 9 countries, delivering enterprise-wide transformations from Brazil to New Zealand, and Norway to South Africa. As the founder of 3Foundry, he is on a mission to co-create experiences for a better tomorrow. 3Foundry focuses on Transformation, Advisory and Innovation. Where to find NiranjanLinkedIn: https://linkedin.com/in/niranjan7879

In this episode of CTO Compass, Mark Wormgoor interviews Mattieu, the CEO and co-founder of Elora, a company specializing in AI voice bots. They discuss the inception of Elora, the challenges faced in developing AI technology, the importance of multilingual capabilities, and the pivot from outbound to inbound calls. Mattieu shares insights on funding strategies, customer use cases, team dynamics, and the competitive landscape of hiring in the AI sector. The conversation concludes with Mattieu's vision for the future of AI in customer interactions and valuable advice for aspiring entrepreneurs.Chapters00:56 Welcome & Mattieu’s Journey02:14 How Elora Was Born04:09 Pivoting to Inbound Voice AI08:58 Challenges of Multilingual Voice Tech15:40 Funding and Growing in Luxembourg24:07 Hiring, Leadership & Team Building33:02 Using AI Tools in Development38:06 AI Hype vs Reality39:59 Future Vision & Lessons LearnedAbout MattieuMattieu is the co-founder at Elora, leveraging generative AI for enhancing business communications. Based in Luxembourg, their company specializes in advanced AI-powered chat and call assistants designed to automate and transform both internal and external business communications.Their technology empowers organizations to manage repetitive interactions seamlessly, enhancing productivity and providing valuable insights through sophisticated AI-driven conversations.With a strong background as a cloud architect and big data engineer, he leads their efforts in deploying state-of-the-art solutions that drive efficiency and innovation. Owning certifications in leading cloud technologies and having extensive experience in AWS, Google Cloud, and Azure, he ensures their solutions are robust, scalable, and tailored to meet the unique needs of each client.If you are looking to enhance your communication strategies with AI, connect with Mattieu.Where to find MattieuElora: https://elora.lu/LinkedIn: https://www.linkedin.com/in/mattieudetaille/