The CTO Compass

How User Psychology Grew a Dating App to 17 Million Users With Almost No Marketing Budget ft. Colin Hodge

Fri, 17 Apr 2026 09:00:00 +0200

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 Takeaways

The 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.

Chapters

00:00 The 14 Year-old Company Owner

05:47 Launching DOWN

12:54 Ad

13:26 The Controversial "Bang With Friends"

17:42 "Outrageous Startup Growth"

24:18 Ad

24:29 Psychology as a Foundation!

28:14 Standing Out Through The AI Noise

30:10 Past Advice and Future Plans!

33:22 Behavioral Improvement and Empathetic Approach

About Colin

Colin 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 Colin

Website: https://colinhodge.com/
LinkedIn: https://linkedin.com/in/ckbhodge
Instagram: https://instagram.com/ckbhodge
Colin'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

Why 95% of AI Pilots Deliver Zero Business Impact and How to Fix Your Foundation ft. Matt Soltau

Fri, 10 Apr 2026 09:00:00 +0200

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 Takeaways

Why most AI pilots fail to deliver business impact despite working in sandbox environments
The hidden risk of disconnected data pipelines and how they break AI in production
Early warning signs your data foundation is not ready for AI
Why point-to-point integrations create long-term complexity and technical debt
How 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 adoption

About Matt

Matt 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.

Chapters

00:00 Dangerous AI Assumption

09:37 Why Pragmatic Solutions aren't Enough

15:08 Ad

15:40 How Important is Compliance?

22:29 When Does the Problem Start?

28:59 Working with Enterprise Organizations

34:17 Dealing with Compliance Complexity

39:07 Ad

39:19 Expensive Integration Mistakes

46:26 Controlling Your Data Foundation!

Where to find Matt

Website: https://www.intellipaas.io/
LinkedIn: https://www.linkedin.com/in/soltaumatt/
YouTube: https://www.youtube.com/@IntelliPaaS

The Software That Can’t Be Wrong: Building Fintech for Millions in Africa ft. Erioluwa Asiru

Fri, 03 Apr 2026 09:00:00 +0200

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 Takeaways

Why fintech changes engineering standards completely and why “good enough” code is never acceptable
How to balance product growth with fraud prevention and system risk
A practical approach to deciding which features to build or reject based on risk vs return
How to scale a lean engineering team without introducing unnecessary process overhead
Why raising the bar for users can be more effective than building complex safeguards
The shift from writing code to leading people, making trade-offs, and owning outcomes

About Erioluwa

Erioluwa 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.

Chapters

00:00 What is Ajo?

06:56 Ad

07:28 Working in Nigerian Financial Technology

13:35 Fraud, Features, and Leadership

22:51 Ad

23:03 Complicated Solutions and Inspiration

26:38 The Future of Circle Funds

29:46 Mentorship Experience

31:05 You Need a Community!

Where to find Erioluwa

Website: https://circlefunds.io
LinkedIn: https://www.linkedin.com/in/asiru-erioluwa/

3 Ways to Build AI Systems That Survive the Real World ft. Sairam Sundaresan

Fri, 27 Mar 2026 09:00:00 +0200

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 systems

About Sairam

Sairam 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.

Chapters

00:00 Industry Real World Failures

05:26 Reliability of AI Models

11:24 Ad

11:57 "AI for the Rest of Us"

16:28 Starting With AI

24:54 Explaining AI to the Board

27:37 Ad

27:48 AI Unrealistic Expectations

32:42 What kind of People does AI Demand?

36:49 Keeping Up with AI

39:15 AI Predictions

Where 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/

AI Risk Is a Design Problem: 3 Questions Every CTO Should Ask Before Their Next AI Release ft. Jill Stover Heinze

Fri, 20 Mar 2026 09:00:00 +0200

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 Takeaways

Why most AI strategies fail before build and how to validate ideas against real user behavior
How generative AI changes risk and why non-deterministic systems require new leadership thinking
How to use risk and governance as a design tool instead of a compliance exercise
Why product-market fit still kills AI initiatives and how to avoid building the wrong thing
What to ask your board and teams to move fast without falling into AI hype and costly mistakes

About Jill

Jill 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.

Chapters

00:00 The Ground Truth

04:38 AI's Hidden Consequences (NIST)

12:47 Ad

13:19 Approaching AI as a CTO

18:45 FOMO in the Corporate World

22:57 Keeping Up with AI

28:42 Ad

28:53 Effectively Using AI

37:27 Talk to Your People!

Where to find Jill

Website: https://www.saddlestitchconsulting.com
LinkedIn: https://www.linkedin.com/in/jill-stover-heinze/
Instagram: https://www.instagram.com/jill_saddlestitchconsult/
YouTube: https://www.youtube.com/@JillHeinze-SaddleStitchConsult
Facebook: https://www.facebook.com/profile.php?id=61581363390571
TikTok: https://www.tiktok.com/@jill_saddlestitchconsult

AGENTS.md Won’t Save You: Design AI Systems You Can Actually Control ft. Craig Kaplan

Fri, 13 Mar 2026 09:00:00 +0200

AI is moving from copilots to autonomous agents, and most tech leaders are not prepared for what that shift means. Craig walks through the real risks behind superintelligence, why AI checking AI is becoming inevitable, and how CTOs and CIOs can design safer, more resilient systems before autonomy outpaces human oversight

Rather than focusing on hype, this episode dives into the alignment problem, 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 models

If 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 Takeaways

Why AI checking AI is not optional as code generation and autonomy scale
What the alignment problem really means for enterprise technology leaders
The limits of guardrails and why prevention at design stage beats patching at deployment
How democratic architectures of multiple agents can reduce systemic risk
Why vendor agnostic, multi model strategies increase resilience and strategic control
How to embed company values into AI systems through training, memory, and architecture
What P(doom) represents and why many leading researchers assign it far higher risk than most executives assume

About Craig

Dr. 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.

Chapters

00:00 How far is AGI?

06:55 What is P(doom)?

16:43 AI Reviewing AI Output

20:54 Dealing with Bad Actors (Human or AI)

25:36 Approaching AI as a Small Scale CTO

30:43 Democracy of AI Agents

35:15 AI Safety Conferences

40:03 AI Models, Open-Source or Big Company?

45:05 Is AI Adoption Keeping Up?

Where to find Craig

LinkedIn: https://www.linkedin.com/in/craigakaplan
Website: https://www.superintelligence.com
Website: https://iqco.com
YouTube: https://www.youtube.com/@iqstudios1

Why Treating AI Like Software will cause Most AI Initiatives to Fail ft. Stephanie Sylvestre

Fri, 06 Mar 2026 09:00:00 +0200

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 economy

About Stephanie

Stephanie 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.

Chapters

00:00 Managing AI with a Human Perspective

06:06 Avatar Buddy

14:04 Automation using AI

24:47 Getting People Into AI

31:05 Working with Smaller Systems

35:16 C-level People and Personal Growth

43:42 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-MEeQ

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 CTOs Burn Out when the Pressure to Deliver Keeps Rising ft. Andrew Hinkelman

Fri, 27 Feb 2026 09:00:00 +0200

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 environments

About Andrew

Andrew 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.

Chapters

00:00 What makes a Successful CTO

05:48 "I need to fix everything"

10:56 Delivery Expectations and Overwork

21:54 What Burnout Looks Like

26:40 When Standard Training Isn't Working

33:05 Bringing People into the Culture

37:54 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/markwormgoor

Contact Us

• Business Email: team@tairi.co

Why Enterprise AI Keeps Disappointing (hint: CoPilot isn’t the Problem) ft. Santosh Kaveti

Fri, 20 Feb 2026 09:00:00 +0200

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 CIOs

Why AI adoption fails without strong data readiness and ownership
What “data as a product” looks like in practice
How to move from AI pilots to production in four to six weeks
Why Copilot often struggles and how to unlock real productivity gains
How to measure AI ROI beyond licenses and usage metrics
Why model-agnostic architecture matters for enterprise AI

About Santosh

With 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.

Chapters

00:00 Knowing When You're in the Wrong Direction

07:44 What is Data Readiness in AI?

12:49 Where Do You Start with AI Data?

17:43 AI Implementation in Your Business

26:11 Microsoft Copilot is Overtaking!

37:04 AI Enterprise Adoption

43:53 Leveraging AI for Big Changes

Where to find Santosh

Website: 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/markwormgoor

Contact Us

• Business Email: team@tairi.co

The Hidden Complexities of SaaS Pricing, CPQ, and Quote-to-Cash ft. Tina Kung

Fri, 13 Feb 2026 09:00:00 +0200

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 scale
How pricing flexibility and personalization create hidden complexity that impacts execution and strategy
Why revenue systems should be treated as core technical infrastructure with direct boardroom impact
What most enterprise AI gets wrong by stopping at summaries instead of removing operational work
How CTOs can simplify revenue workflows to improve clarity without triggering a large transformation project

Chapters

00:00 Handling Business Overload

07:09 Simplifying the Process

14:47 The Hurdles of Implementation

18:31 Problems with Old Contracts

23:11 OpenAI's Strict Timeline

25:54 Complexity under Simplicity

31:26 Implementing AI

35:40 What's Next?

About Tina

Tina 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 Tina

LinkedIn: https://www.linkedin.com/in/tinakung/
Website: https://nue.io

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

Fri, 06 Feb 2026 09:00:00 +0200

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 bottlenecks
the difference between delegation and abdication
how to work effectively with visionary CEOs without drowning in continuously changing priorities
why AI often amplifies leadership problems instead of fixing them
and what buyers look for when evaluating whether a business can scale or exit

Chapters

00:00 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 David

David 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 David

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

Fri, 30 Jan 2026 09:00:00 +0200

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 one
How to design tech roles around outcomes instead of outdated requirements
Where great tech talent actually comes from today
How remote work has changed hiring signals and expectations
Why adaptability matters more than years of experience in the AI era
The 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.

Chapters

00:00 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 Bill

Bill 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

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

Fri, 23 Jan 2026 09:00:00 +0200

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.

Chapters

00:00 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 Matt

Matt 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

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

Fri, 16 Jan 2026 09:00:00 +0200

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 impact
Build cultures that amplify innovation (not just output)
Spot the hidden signals that sabotage diversity and creativity
Lead with courage, even when you feel like an imposter

Chapters

00:00 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 Telle

Telle 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 Telle

Telle Whitney's book: Rebooting Tech Culture: How to Ignite Innovation and Build Organizations Where Everyone Can Thrive
Website: https://www.tellewhitney.com/
LinkedIn: https://www.linkedin.com/in/telle-whitney/

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

Fri, 09 Jan 2026 09:00:00 +0200

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

🎯 Learn how to:

Escape the trap of surface-level innovation
Use AI as a strategic co-pilot, not a tactical bolt-on
Transform from technical expert to strategic leader
Lead with clarity, purpose, and structure, especially in fast-scaling environments

Chapters

00:00 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 Loic

Loic 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/

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

Fri, 19 Dec 2025 09:00:00 +0200

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.

Chapters

00:00 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 Hollis

William 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/

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

Fri, 12 Dec 2025 09:00:00 +0200

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.

Chapters

00:00 - 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 Scott

With 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/

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

Fri, 05 Dec 2025 09:00:00 +0200

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.

Chapters

00:00 - 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 Margaret

Dr. 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/

Revolutionizing Logistics with AI ft. David Soileau

Fri, 28 Nov 2025 09:00:00 +0200

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.

Chapters

00:00 – Gopher’s Origin & Pivot

04:18 – Why Logistics Needs Tech

07:40 – Going Digital in Old Industries

10:16 – AI Features: Pic-to-Ship & GoPilot

12:12 – Tech Challenges & Early Mistakes

16:21 – Team, CTO, and Automation

20:07 – Fixing Legacy Logistics

24:23 – Techstars, Expansion & Future of AI

About David

David 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

The Future of Work: AI and Human Roles ft. Mike Todasdo

Fri, 21 Nov 2025 09:00:00 +0200

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.

Chapters

00:00 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 Michael

Michael 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 Carnegie

Where to find Michael

• LinkedIn: https://www.linkedin.com/in/todasco/

• Website: https://todasco.lovable.app/

Debunking Innovation Myths ft. Coby Skonord

Fri, 14 Nov 2025 09:00:00 +0200

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.

Timestamps

00:00 – Leaving EY to Build Ideawake

02:35 - Why Innovation Fails Inside Big Organizations

03:47 - Building a Culture That Enables Innovation

05:26 - Turning Ideas into Impact

09:38 - Innovation in Healthcare and Regulated Industries

10:37 - The CTO’s Role in Driving Innovation

13:50 - Escaping the Budget Trap

19:35 - Breaking Through Enterprise Barriers

26:36 - The Future of Innovation and the Role of AI

About Coby

Coby 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/

Building a Health Tech Revolution ft. Bart Spangenberg

Fri, 07 Nov 2025 09:00:00 +0200

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.

Timestamps

00:00 From Personal Struggles to a Mission in Health

02:49 Learning to Code & Building NewU

06:39 Lessons from Working with an Agency

08:49 What NewU does

10:59 Privacy by Design and Trust in Health Data

14:19 Digitizing the Dutch PMO: Compliance Meets Health

15:50 Leading a Remote International Development Team

20:04 Hiring for Mindset, Growth, and Culture Fit

26:29 Applying Behavioral Science to Product Design

32:36 The One Thing: Focus and Decision-Making in Leadership

About Bart

Health, 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 Papasan

Where to find Bart

• Website: https://www.newu-app.io

• LinkedIn: https://www.linkedin.com/in/bartspangenberg/

Revolutionizing Audio Production with AI with Peadar Coyle

Fri, 31 Oct 2025 09:00:00 +0200

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.

Timestamps

00:00 Building AI Before the Hype

03:41 Surviving the GPT wave

05:57 Defensibility without mega-rounds

07:30 What AudioStack actually does

08:11 One-to-many: turning unscalable into scalable

12:06 Thin wrappers vs thick platforms

14:58 Model churn & provider neutrality

19:34 Ship faster: the metric that matters

24:17 Open Source Communities vs. Business Customers

26:40 Scaling across locations

30:25 Government advice

36:05 CTO and Startup Lessons

About Peadar

Peadar 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 Peadar

Audiostack Website: http://www.audiostack.ai/
Peader's LinkedIn: https://www.linkedin.com/in/peadarcoyle/
and on Youtube: https://www.youtube.com/c/Aflorithmic

Navigating Government Contracts as an Expat with Tony Kyriakidis

Fri, 24 Oct 2025 09:00:00 +0200

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.

Timestamps

00:00 Introduction

02:19 Learning Dutch & Fitting in

10:16 Landing the First Government Client

15:27 Transitioning from Agency to Product

19:45 What Mission Control actually does

24:36 Leadership & Operations at Scale

33:36 AI in Incident Management

38:51 Risk Planning & Entrepreneurial Mindset

42:16 Freedom and Entrepreneurship

About Tony

Tony 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 Tony

Website: https://nevron.io
LinkedIn: https://www.linkedin.com/in/tony-kyriakidis
Instagram: https://instagram.com/iam.tony

Navigating the Future of Remote Work with Nola Simon

Fri, 17 Oct 2025 09:00:00 +0200

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.

Chapters

00:00 Intro to Remote Work & Flexibility

05:34 Creating Connection in Remote Teams

10:55 Async workflows, documentation, and AI

13:31 Earning trust for knowledge sharing

15:16 Measuring trust via outcomes & psychological safety

29:04 Strategic foresight: scenarios and adaptability in AI turbulence

44:35 Playbook for first-time distributed CTOs

About Nola

Nola 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

Visionary and Integrator Dynamics with Kelsey Daingerfield

Fri, 10 Oct 2025 09:00:00 +0200

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.

Chapters

00:00 Introduction & Background

02:13 Visionary vs. Integrator (Rocket Fuel)

05:00 Transition into Entrepreneurship

08:24 Client Work Examples

11:28 Recognizing Operational Red Flags

18:39 Delegation & Leadership Challenges

25:33 Change Management & Communication

31:15 AI in Operations

37:42 Common Leadership Pitfalls

40:14 Success Story

43:23 Final Advice & Wrap-up

About Kelsey

Kelsey 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 Kelsey

Website: https://www.kelseydaingerfield.com/
LinkedIn: https://www.linkedin.com/in/kelseydaingerfield/
Instagram: https://www.instagram.com/kelseydaingerfield/

The Future of Software Development with Ahmed Bashir (DevRev)

Fri, 03 Oct 2025 09:00:00 +0200

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.

Chapters

00:00 Going from Apple to DevRev

08:13 Built-In AI: How DevRev Differs from Other Platforms

15:44 Writing as a Superpower in the Age of AI

22:10 Knowledge Graphs vs. Vector Databases

25:22 Using AI to enhance Work Observability

35:43 Leading Remote Engineering Teams at Scale

41:57 How an AI company uses AI tools in Software Development

46:48 The Future of AI

About Ahmed

Ahmed 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 Ahmed

DevRev: https://devrev.ai/
LinkedIn: https://www.linkedin.com/in/ahmedmbashir/

From Spreadsheets to AI Agents with Zulfiya Forsythe

Fri, 26 Sep 2025 09:00:00 +0200

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.

Chapters

00:00 Introduction

08:36 The Role of AI in Data Management

10:26 Launching a Business during COVID

18:05 Client Impact Stories

22:35 AI in Construction and Plumbing

31:30 Financial Impact of AI

38:51 Skills for Tech Leaders in the AI Era

44:07 Lessons Learned

About Zulfiya

It 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 Zulfiya

Website: https://omadligroup.com/
Youtube: https://www.youtube.com/@zulfiyaforsythe
Instagram: https://www.instagram.com/zulfiyaforsythe/
LinkedIn: https://www.linkedin.com/in/zulfiya-forsythe-akbarova-cpa-0214b98

From Tinkerer to CTO with Mattia Peiretti

Fri, 19 Sep 2025 09:00:00 +0200

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.

Chapters

00:46 Intro & Early Tech Obsession

05:04 From School Projects to Running an Agency

12:10 Scaling Up at Pararius

16:17 Inside the Antler Experience

22:58 Finding a Co-Founder & PocketCFO’s Start

29:32 Why SMEs Matter & The Future of Finance

41:00 Building Fast, Smart Tech without Regrets

50:42 Lessons & Advice for Aspiring CTOs

About Mattia

Mattia 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 Mattia

LinkedIn: https://www.linkedin.com/in/mattiapeiretti/
Website: https://mattiapeiretti.com/
PocketCFO: https://pocketcfo.io/

The Journey of a Global Leader w/ Niranjan Sridhar

Fri, 12 Sep 2025 10:00:00 +0200

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.

Chapters

00:00 Introduction to Niranjan

04:50 Pivotal Moments and Decisions in Career

08:58 The Philosophy of Co-Creation and Three Foundry

13:45 Success Factors in Large Transformation Programs

22:42 Transitioning from Program Director to CIO

26:11 Transforming Business Processes: The Lipton Case Study

31:19 Navigating the AI Landscape: Learning and Implementation

39:19 Adapting to Rapid Technological Change: The Future of Business Programs

43:15 Lessons from Setbacks: The Importance of Change Management

47:59 Leadership Insights: Authenticity and Continuous Learning

About Niranjan

Born 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 Niranjan

LinkedIn: https://linkedin.com/in/niranjan7879

Revolutionizing Customer Service with AI w/ Mattieu Detaille

Fri, 05 Sep 2025 09:00:00 +0200

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.

Chapters

00:56 Welcome & Mattieu’s Journey

02:14 How Elora Was Born

04:09 Pivoting to Inbound Voice AI

08:58 Challenges of Multilingual Voice Tech

15:40 Funding and Growing in Luxembourg

24:07 Hiring, Leadership & Team Building

33:02 Using AI Tools in Development

38:06 AI Hype vs Reality

39:59 Future Vision & Lessons Learned

About Mattieu

Mattieu 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 Mattieu

Elora: https://elora.lu/
LinkedIn: https://www.linkedin.com/in/mattieudetaille/