The CTO Compass

Mark Wormgoor
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  • TECHNOLOGY

The CTO Compass is a podcast about CTO, CIO, and tech leadership - on strategy, scaling, teams & bringing clarity to technology leadership for real boardroom impact. Hosted by Mark Wormgoor, each episode features candid conversations with experienced CTOs, CIOs, and senior tech leaders from startups through to large enterprises. The focus is on the real work of leading in tech: – Setting clear tech strategy that aligns with business goals – Scaling teams and culture – Making high-stakes decisions under pressure – Navigating the transition from hands-on engineer to executive leader This is not a hype show, nor a theoretical leadership podcast. Guests share hard-won lessons, mistakes, and practical insights from the moments that mattered most - when clarity was missing, heavy decisions needed to be made, and leadership was tested. If you’re a CTO, CIO, or tech leader looking to sharpen your thinking, increase your influence, and create real impact in the boardroom, The CTO Compass is built for you.

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

    6D AGO

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

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

    43 min
  2. Hiring Is Broken for Tech Leaders. Here’s What Actually Works Today ft. Bill Kasko

    JAN 30

    Hiring Is Broken for Tech Leaders. Here’s What Actually Works Today ft. Bill Kasko

    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 ones If 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 IT 08:29 Infrastructure and Security Today 15:46 Where To Start With Recruitment 24:34 What's The Secret with Recruitment 30:50 Approaching Remote Work 36:56 The Hiring IT Landscape 42:33 Hiring In Today's Market 46:52 Hiring Retention 50:26 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

    54 min
  3. How to Spot Revenue Leaks and Align Tech to Business Goals. Lessons from a Fractional CTO ft. Matt Dixon

    JAN 23

    How to Spot Revenue Leaks and Align Tech to Business Goals. Lessons from a Fractional CTO ft. Matt Dixon

    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 Leadership 04:16 Revenue Leaks and Fractional CTO Work 08:41 Working with Existing Tech Teams 13:02 Managing Expectations and Misunderstandings 16:39 Code Program and Misaligned Priorities 20:58 Technical Debt and Shiny Object Syndrome 26:47 What CTO's Should Be Doing 28:55 AI in Tech and Business About 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

    33 min
  4. Beyond the Lone Genius: Telle Whitney on Rethinking Leadership for Today’s CTOs and CIOs

    JAN 16

    Beyond the Lone Genius: Telle Whitney on Rethinking Leadership for Today’s CTOs and CIOs

    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 imposter Chapters00:00 From Theater to Computer Science 05:39 The Grace Hopper Celebration 11:27 Rebooting Tech Culture 20:12 Meritocracy and The Lone Genius 26:15 What a Company actually needs 32:44 Does Inclusivity Improve The Output? 34:28 AI4ALL 38:43 Taking Risks About 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/

    43 min
  5. The 80/20 that Actually Moves the Needle ft. Loic Potjes

    JAN 9

    The 80/20 that Actually Moves the Needle ft. Loic Potjes

    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 environments Chapters00:00 Worldwide CEO Experience Perspective 06:23 Transitioning for the Future 11:30 Personal Growth as a CEO 14:07 Business-Tech Mistakes 21:52 Change and Improvement 29:22 Coaching Growth 34:49 Business AI Integration 41:50 Navigating the AI Hype 48:10 Simplifying Your Pitch About 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/

    51 min
  6. RaiseAI: Cutting the Time for a Capital Round in HALF ft. William Hollis

    12/19/2025

    RaiseAI: Cutting the Time for a Capital Round in HALF ft. William Hollis

    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 Career 06:20 When to use Tech and People 08:08 Implementing Tech into Real Estate (Raise AI) 12:45 Streamlining "32 Touch points" with AI 19:31 Building a Team and AI Adoption 24:06 AI Future-proofing and Relationships 28:36 Why Real Estate AI and Building Culture 33:02 The Future of Raise AI About 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/

    35 min
  7. Reinventing Talent: on Clarity, Culture, and AI w/ Scott Morris

    12/12/2025

    Reinventing Talent: on Clarity, Culture, and AI w/ Scott Morris

    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 HR 07:35 - Solving The Problem with Hiring 14:39 - Athena and Propulsion 21:20 - Importance of Operational Roles 25:04 - Athena as a Teammate 29:41 - Collaborating with Tech 32:08 - Culture in the Hiring Process 34:32 - Are You Ready to Hire? 38:41 - Future of HR Tech 41:44 - Hiring and Managing Advice About 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/

    46 min
  8. Don’t Wait for All the Data: on Courage, Culture, and AI ft. Margaret Heffernan

    12/05/2025

    Don’t Wait for All the Data: on Courage, Culture, and AI ft. Margaret Heffernan

    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 Uncertainty 03:57 - Curiosity in Business 10:15 - Measurements, Data, and KPIs 12:51 - Letting AI think for Us 16:29 - Growing Leadership Skills 26:31 - CEO Coaching Experience 33:29 - 9-9-6 Mentality 38:00 - Business Trends 40:00 - Social Capital with Global Teams 45:40 - Margaret's Essential Question About 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/

    49 min
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About

The CTO Compass is a podcast about CTO, CIO, and tech leadership - on strategy, scaling, teams & bringing clarity to technology leadership for real boardroom impact. Hosted by Mark Wormgoor, each episode features candid conversations with experienced CTOs, CIOs, and senior tech leaders from startups through to large enterprises. The focus is on the real work of leading in tech: – Setting clear tech strategy that aligns with business goals – Scaling teams and culture – Making high-stakes decisions under pressure – Navigating the transition from hands-on engineer to executive leader This is not a hype show, nor a theoretical leadership podcast. Guests share hard-won lessons, mistakes, and practical insights from the moments that mattered most - when clarity was missing, heavy decisions needed to be made, and leadership was tested. If you’re a CTO, CIO, or tech leader looking to sharpen your thinking, increase your influence, and create real impact in the boardroom, The CTO Compass is built for you.

Information

  • Creator
    Mark Wormgoor
  • Years Active
    2025 - 2026
  • Episodes
    21
  • Rating
    Clean
  • Copyright
    © Copyright 2025 Tairi
  • Show Website
    The CTO Compass