The CTO Compass

Mark Wormgoor

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

  1. 11h ago

    Why Enterprises Regret Public Cloud (and What They're Bringing Back) ft. Sabina Anja

    Mark sits down with Sabina Anja, Chief Technologist of VMware Cloud Foundation, to explore why patience has become the most critical virtue in enterprise technology leadership. Sabina discusses why large organizations are increasingly regretting full public cloud migrations, how AI demands are driving enterprise buyers to the back of the hardware line, and what European digital sovereignty actually looks like in practice. From resurrecting legacy techniques like tape storage and memory tiering to navigating the human politics of infrastructure migrations, this conversation delivers an honest, practical look at modern IT strategy. Key Takeaways • Infrastructure success depends far more on managing stakeholder egos, budgets, and organizational patience than on the technical execution itself. • Rising public cloud costs and unpredictable AI compute expenses are driving businesses back toward hybrid architectures and private cloud repatriation to retain operational and financial control. • Hyperscalers currently dominate hardware allocation, requiring enterprise leaders to extend asset lifecycles through capacity planning, tiering, and component reuse. • Digital sovereignty is better achieved through practical control and stack independence than through waiting for local hardware supply chains that do not yet exist. • Organizations can free up substantial budget and compute capacity simply by auditing underutilized systems, consolidating redundant tooling, and eliminating set-and-forget configurations. • Inspiring technical teams by framing resource constraints as creative engineering challenges produces far greater engagement and efficiency than issuing top-down mandates. About SabinaSabina Anja is a Chief Technologist with over two decades of hands-on experience, from embedded systems and network engineering all the way to AI infrastructure and private cloud strategy. She has spent the better part of her career at the layer where enterprise technology actually runs, designing, building, and operating the systems that organizations depend on at scale. In parallel, she built a self-funded open-source services company to profitability in its first year, reaching 150 customers across three continents with 89% customer retention and no outside capital. She is one of the rare guests who can speak to both the deepest technical layer and the boardroom conversation, and today she is here to talk about what enterprises are getting wrong before they ever commit to an AI infrastructure strategy. Chapters00:00 A Story of Lack Thereof 04:05 Becoming a Chief Technologist 09:17 Ad 09:58 Enterprise Infrastructure Today 14:33 The Future of Infrastructure 18:57 The Future of Networking 23:10 Ad 23:26 The Hardware Crisis 27:03 Sovereignty in The Age of AI 31:10 Maneuvering Tech Today 37:21 Everybody Wants to Do AI! Where to find Sabina• Website: https://www.vmware.com/ • Website: https://critical-path.is/ • LinkedIn: https://www.linkedin.com/in/sabinaanja/ My Socials• Website: https://tairi.co • LinkedIn: https://www.linkedin.com/in/mwormgoor • Instagram: https://www.instagram.com/markwormgoor Contact Us• Business Email: team@tairi.co

    Why Enterprises Regret Public Cloud (and What They're Bringing Back) ft. Sabina Anja

  2. Nov 6

    Chat Is the Lousiest Way to Use AI ft. Akhil Mantripragada

    Mark sits down with serial entrepreneur and Pie CTO Akhil Mantripragada to discuss software architecture, user experience, and practical artificial intelligence. Akhil shares how Pie scaled to more than 3,000 small business customers and secured a nearly $20 million Series A within 14 months by solving customer acquisition for local merchants. Akhil explains why his first three hires were product designers instead of software engineers, why open-ended prompting fails everyday operators, and how replacing chat with deterministic, inbox-style workflows drives real adoption. He also breaks down Pie's go-to-market playbook through vertical SaaS partnerships, the low-risk rollout strategy behind their front-desk voice agent, and how engineering leaders can transition into customer-obsessed product engineers. Key Takeaways • Open-ended chat prompts create friction for everyday users, making deterministic, inbox-style approval systems far more effective for software adoption. • Small business owners value tangible business outcomes like new customer growth over artificial intelligence buzzwords or technical novelty. • Distributing through white-label partnerships with existing vertical SaaS platforms enables software startups to scale customer acquisition rapidly without bloated sales teams. • Deploying voice agents in low-risk stages, such as handling ad-driven inquiries and after-hours calls first, allows merchants to build confidence before full system integration. • Technical leaders can bridge the gap between engineering and product by shadowing customer calls and watching for the physical "eyes light up" reaction to prototypes. • Long-term product defensibility in modern software relies on capturing rich customer context rather than depending on commoditized foundational models. About AkhilAkhil Mantripragada is Co-founder and CTO of Pie, an AI-native marketing platform for SMBs. A 2x founder and software engineering leader, Akhil has built and launched more than 10 products across AI, education technology, and enterprise software. He previously served as New Ventures Tech Lead at Toast and spent more than seven years as a Software Architect and Engineering Leader at Pragya Systems, where he led the integration of his acquired startup, Edulinc, and helped launch six products across more than 10 institutions. Earlier in his career, Akhil co-founded Intuitive Inventions, selling its product to UTSA before attending Columbia University. His work sits at the intersection of AI, product design, and applied engineering, with a focus on building practical technology that meets users where they are. Chapters00:00 Say Yes! 02:36 From Toast to Pie 07:02 Selling AI to Non-tech people 10:51 AI Answering the Phone 13:09 Handling Onboarding 15:10 Ad 15:51 Being Close to The Customer 18:40 Customer Wants vs Needs 20:43 The Age of Custom Solutions! 24:37 AI Chat and Service Pricing 29:30 Ad 29:46 Talking to Customers 35:32 LLMs Changing The Software Industry 39:33 The Future of Pie Where to find Akhil• Website: https://getpie.com/ • LinkedIn: https://www.linkedin.com/in/akhileshmantripragada/ My Socials• Website: https://tairi.co • LinkedIn: https://www.linkedin.com/in/mwormgoor • Instagram: https://www.instagram.com/markwormgoor Contact Us• Business Email: team@tairi.co

    Chat Is the Lousiest Way to Use AI ft. Akhil Mantripragada

  3. Oct 30

    Should We Worry? How a Non-Technical Founder Built Her Own Software With Lovable and Claude ft. Audrie Spjute

    How does a beauty studio owner of over twenty years end up building and launching her own software platform? In this episode of The CTO Compass, host Mark Wormgoor sits down with esthetician and salon owner Audrie to discuss how she tackled financial blind spots by creating Elona, an all-in-one software integrating booking, point-of-sale, and banking data. Audrie explains how relying on bank balances led to recurring cash flow surprises, why hiring an outside developer stalled, and how she used Claude, Lovable, and Vercel to build the solution herself. Whether you are a business owner struggling with financial visibility or a tech leader watching the evolution of AI-powered development, this conversation highlights the advantage of solving problems you have lived firsthand. Key Takeaways • Managing a business solely by looking at available bank balances hides real operational costs and leads to recurring cash shortages. • Service professionals frequently receive thorough technical craft training but lack foundational business education on bookkeeping and value-based pricing. • Generative AI tools and low-code builders enable non-technical founders to architect and deploy functional software products on their own. • Testing a product internally with your own staff produces immediate, candid feedback that external customers rarely take the time to share. • Firsthand domain experience in an industry gives founders a massive advantage when designing software tailored to real user needs. • Adopting a mindset that questions why you cannot learn a new skill allows entrepreneurs to overcome intimidation and solve their own problems. About AudrieAudrie Spjute is the founder of Elona, the financial OS turning beauty pros' booking and banking data into real-time profit clarity — no spreadsheets, no guesswork. She built it after running her own brow studio and realizing "fully booked" doesn't mean "actually profitable." Now she's helping beauty professionals everywhere run their business like a CEO, not just work in it. Chapters00:00 Financing in the Beauty Industry 03:05 Looking at Your Numbers 04:57 Creating Your Own Software 08:28 Ad 09:08 Managing a Software and a Beauty Business 11:56 Thinking Bigger, Dreaming Bigger 13:44 Hurdles of Making Your Own Software 17:39 Ad 17:55 The Beauty Industry's Perspective 19:39 The Future of Elona 22:12 Believe In Yourself! 23:19 3 Years Into Elona Where to find Audrie• Website: https://getelona.co • LinkedIn: https://www.linkedin.com/in/audriespjute/ • Instagram: https://www.instagram.com/therealaudrie/ • YouTube: https://www.youtube.com/@AudrieSpjute My Socials• Website: https://tairi.co • LinkedIn: https://www.linkedin.com/in/mwormgoor • Instagram: https://www.instagram.com/markwormgoor Contact Us• Business Email: team@tairi.co

    Should We Worry? How a Non-Technical Founder Built Her Own Software With Lovable and Claude ft. Audrie Spjute

  4. Oct 23

    How to Get Your 2027 AI Budget Approved

    host Mark Wormgoor tackles the challenges of corporate IT budgeting and explains why conventional metrics like hours saved and software utilization fail to convince the CFO. Reflecting on insights shared by Anaconda VP of Engineering Emilie Schario, Mark examines the three core missteps corporate leaders make with AI deployments, from isolated micro-pilots to restrictive licensing strategies. Learn how to shift from raw spend tracking to measuring real units of customer value, redesign workflows from end to end, and build executive buy-in to protect your AI initiatives. Key Takeaways • CFOs routinely reject soft metrics like saved hours or user adoption surveys, demanding verified financial returns through revenue growth or tangible operational savings instead. • Tracking AI spend in isolation is counterproductive because usage naturally trends upward, requiring leaders to measure costs against delivered units of customer value. • Automating a single isolated task inside a larger workflow produces no measurable financial return unless the underlying process is overhauled end to end. • Restricting software access to a small group of power users prevents broader AI literacy and stalls company-wide modernization. • Technology teams must move away from passive service delivery by co-designing initiatives and sharing business case accountability directly with business unit leaders. • Securing board alignment on organization-wide AI literacy well ahead of budget cycles prevents critical technology funding from being eliminated by finance. Chapters00:00 Intro 03:02 1st Point 05:45 2nd Point 09:37 3rd Point 11:18 Outro My Socials• Website: https://tairi.co • LinkedIn: https://www.linkedin.com/in/mwormgoor • Instagram: https://www.instagram.com/markwormgoor Contact Us• Business Email: team@tairi.co

  5. Oct 16

    AI Spend Is a Bad Metric: How to Measure AI ROI in Your Engineering Team instead ft. Emilie Schario

    What are you actually getting for all that AI spend? Host Mark Wormgoor sits down with Emilie Schario, VP of Engineering at Anaconda and co-founder of Kilo, the agentic engineering platform Anaconda acquired this year. Emilie's answer is blunt: AI spend is a bad metric, because usage only moves in one direction. The number that matters is what the spend returns, and she gives engineering leaders a simple place to start measuring it. Emilie walks through the equation behind AI ROI, why pull requests merged is the best available proxy for customer value created, and why the size of a pull request does not matter. She explains how software development stopped being a funnel and became a straight tube, what that does to planning and validation, and why teams now have to be willing to kill features after shipping them. Along the way she covers running Kilo without product managers, the one place a PM is still essential, and how to choose models when 500 of them are on the menu. Key Takeaways AI spend only moves in one direction, so tracking the spend itself tells leadership nothing about whether the investment is working.AI spend divided by pull requests merged gives engineering leaders a practical measure of cost against customer value created.Revenue is the ideal measure of customer value, but long enterprise sales cycles make it too lagging to steer by, so lean on DORA-style delivery metrics instead.The size of a pull request does not matter. A one-line outage fix and a 50,000-line feature are both one unit of customer value, and the distribution averages out.Software development is no longer a funnel. Shipping quickly and learning from real users beats planning, validating and wireframe testing up front, as long as you are willing to kill what nobody uses.Tools do not change culture. Rolling out AI without changing how teams operate and coordinate is the biggest drag on engineering organizations right now. About EmilieEmilie is VP, Engineering at Anaconda and the former cofounder of Kilo (acquired by Anaconda), where she focuses on turning AI investment into real engineering output. She operates at the intersection of AI tooling, engineering org design, and the day-to-day realities of running high-performing teams, helping organizations translate innovation into measurable impact. Chapters00:00 Measuring AI ROI 06:56 How AI Changes Workflow 12:26 Ad 13:07 From Politics to Engineering 17:48 A Different Perspective on Data 20:21 Should You Have a Product Manager? 24:24 Ad 24:41 AI in This Age 32:24 How AI Changes Culture 37:10 Choosing The Correct Model Where to find Emilie• LinkedIn: https://www.linkedin.com/in/emilieschario/ • Website: https://kilo.ai/ • Website: https://www.anaconda.com/ My Socials• Website: https://tairi.co • LinkedIn: https://www.linkedin.com/in/mwormgoor • Instagram: https://www.instagram.com/markwormgoor Contact Us• Business Email: team@tairi.co

    AI Spend Is a Bad Metric: How to Measure AI ROI in Your Engineering Team instead ft. Emilie Schario

  6. Oct 9

    Too Good to Be Promoted: Why Being the Best at Your Job Keeps You Stuck and What to Change

    Are you so good at your job that you cannot get promoted? In this solo episode of the CTO Compass Podcast, we explore the paradox of being "too good to move up" and why high praise can sometimes keep your career locked in place. Drawing from a personal experience managing identity systems at a major bank to key insights from a conversation with Kathy Eastwood, this episode breaks down why execution-focused tech leaders get trapped in operational roles. You will learn actionable strategies to build a successor, delegate effectively, and make yourself replaceable so you can step into higher leadership without burning bridges. Key Takeaways • Being exceptionally reliable in execution can lock you into your current role because leadership relies on you to keep things running smoothly. • Leaders often hesitate to promote top performers because replacing a proven operator creates operational risk for the business. • Advancing your career requires actively mentoring a replacement by involving them in complex tasks and letting them learn through hands-on experience. • Successors must be introduced to stakeholders and given public credit so leadership clearly sees that your position is covered. • Moving into higher leadership requires balancing your operational strengths with strategic vision, collaboration, and stakeholder management. • Developing a clear succession plan ensures you can transition or exit without leaving the organization vulnerable or burning bridges. Chapters00:00 Intro 02:09 1st Point 04:57 2nd Point 08:37 3rd Point 09:39 Outro My Socials• Website: https://tairi.co • LinkedIn: https://www.linkedin.com/in/mwormgoor • Instagram: https://www.instagram.com/markwormgoor Contact Us• Business Email: team@tairi.co

    Too Good to Be Promoted: Why Being the Best at Your Job Keeps You Stuck and What to Change

  7. Oct 2

    The Strongest Operator Won't Make a Leader: How to Add Vision and Collaboration Without Faking It ft. Kathy Eastwood

    How do you lead successful organizational change when technical execution alone is not enough? Host Mark Wormgoor sits down with Kathy Eastwood, former Chief People Officer and author of The E3 Leadership Code. Kathy breaks down why tech and operational leaders often struggle with change management, and reveals the framework needed to bridge the gap between execution and long-term vision. Discover why true leadership requires balancing three roles simultaneously: the Visionary, the Collaborator, and the Operator. Kathy shares actionable strategies on how to build influence without formal authority, cascade vision effectively, and break down organizational silos. She also unpacks real-world case studies from her corporate career at HP, demonstrating how taking a people-first approach directly drives high performance and profitability. Key Takeaways • Driving lasting organizational change requires operating as a Visionary, a Collaborator, and an Operator simultaneously. • Successful execution requires learning how to influence and align people when you lack direct authority over them. • Shift from the Golden Rule to the Platinum Rule by adapting your communication style to treat team members the way they want to be treated. • A strategy must be communicated at least seven times across multiple management layers to achieve true organizational alignment. • Focusing on employee engagement and well-being directly boosts productivity and can increase profitability by 23%. • Sharing a personal leadership profile outlining your values and work style drastically accelerates trust across remote and global teams. About KathyKathy Eastwood is a leadership strategist, executive advisor, and CEO of E Equals Why with over thirty years of executive experience across the technology sector. She began her career as a CPA at Ernst & Young and went on to hold diverse roles across startups and global corporations, including Chief People Officer, pre-sales, consulting, and Chief of Staff for R&D at Hewlett Packard Enterprise. Throughout her corporate career, she specialized in driving complex organizational transformations, managing mergers and acquisitions, and scaling cross-functional operations. As the author of The E3 Leadership Code: A Human Approach to High Performance, Kathy helps executives close the gap between strategic intent and everyday execution. Her system equips leaders to balance clear vision, authentic connection, and disciplined operations while leveraging emotional intelligence to sustain results. Today, she advises organizations on building high-trust cultures, breaking down silos, and increasing profitability through people-first leadership. Chapters00:00 From CPA to Consulting 02:14 Managing Operations vs People 06:41 Ad 07:22 Getting to a Vision 15:31 Managing Burnout 18:14 Money Ball Project 23:06 Ad 23:22 Raising Engagement, Cutting Costs 27:52 Communication ≠ Alignment 30:10 Building Trust with Your Teams 33:49 Developing Your Leadership Skills 36:55 Starting with Awareness Where to Find Kathy• LinkedIn: https://www.linkedin.com/in/kathyeastwood/ • Instagram: https://www.instagram.com/kathyeastwoodleadership/ • YouTube: https://www.youtube.com/channel/UC3cYFAUj2Bvf3meKjBZmkGA • Website: https://www.eequalswhy.com • Book: https://www.kathyeastwood.com/book My Socials• Website: https://tairi.co • LinkedIn: https://www.linkedin.com/in/mwormgoor • Instagram: https://www.instagram.com/markwormgoor Contact Us• Business Email: team@tairi.co

    The Strongest Operator Won't Make a Leader: How to Add Vision and Collaboration Without Faking It ft. Kathy Eastwood

  8. Sep 25

    Deep-dive One Hour a Month: How IT Leaders See What Their Reports Never Show

    High-level dashboard reports look clean and simple, but aggregated data frequently hides critical operational mistakes and distorts reality. In this episode, 30-year IT veteran Mark Wormgoor shares why effective leadership requires mastering the distance from your work by balancing granular deep-dives into raw data with periodic offline strategic reflection. Key Takeaways • Aggregated dashboard summaries often round or omit critical details, masking - operational problems behind clean metrics. • Effective oversight requires leaders to occasionally step past high-level reports and directly inspect raw data at the source. • Scheduling just one hour per month to observe front-line operations or review line-item data can prevent costly decision-making errors. • Setting aside half a day each quarter completely offline gives leaders the necessary distance to evaluate long-term priorities and habits. • Successful business leadership depends on finding the right balance between deep-dive operational checks and high-level strategic perspective. Chapters00:00 Intro 02:08 Your Numbers 05:24 Own Your Work 07:23 The Habit 08:55 Outro My Socials• Website: https://tairi.co • LinkedIn: https://www.linkedin.com/in/mwormgoor • Instagram: https://www.instagram.com/markwormgoor Contact Us• Business Email: team@tairi.co

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Ratings & Reviews

5
out of 5
2 Ratings

About

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

Information

  • Creator
    Mark Wormgoor
  • Years Active
    2025 - 2026
  • Episodes
    52
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Tairi
  • Show Website
    The CTO Compass