In this episode, Jeff Mains sits down with Barbara Wittmann, a 25-year veteran of IT transformation who has pioneered the concept of "human infrastructure" - the invisible framework of trust, clarity, and collaboration that determines whether technology projects succeed or fail. Barbara shares her journey from mountain biking and logistics to SAP consulting, and how she discovered that most technology failures are actually people problems in disguise.

She introduces her four-pillar model for preventing costly project detours, explains why people development should be a permanent IT budget line item (not a one-time HR initiative), and reveals how AI is raising the bar on what humans need to do best. The conversation explores psychological safety, shared mental models, limiting beliefs, and why wisdom drawn from indigenous cultures can help modern SaaS leaders build more resilient organizations.

[4:56] - Technology problems are almost always people problems - software can't fix misalignment, confusion, or teams that weren't brought along for the change

[8:35] - Human infrastructure is the framework where departments work seamlessly together, end-to-end processes are understood, and people have artifacts to help them navigate complexity

[10:14] - Shared mental models are critical - creating a high-level map of systems, data elements, and functions helps everyone align on what changes will impact

[12:20] - People development should be an OPEX line item in IT budgets, not a one-time HR initiative - we upgrade servers continuously but treat people upgrades as "one and done"

[16:15] - Empowering the middle layer of organizations can save about 20% on consulting spend because in-house people already have the knowledge

[20:20] - The four-pillar model: Understand the problem → Condense it → Create a solution → Get people excited about it (most teams skip understanding the problem)

[22:32] - The dual ecosystem approach: Train people in a cross-industry environment where they can practice without fear, then bring learnings back to their organization

[25:53] - Once 25% of your middle layer adopts a new mindset, you see behavioral shifts ripple throughout the entire organization

[29:00] - Indigenous wisdom teaches that everything is connected (ecosystems) and everything works in cycles - nature isn't "on" all the time

[34:27] - Limiting beliefs often sound like "I can't do that, I've never done that before" - when your instant reaction is "no," pause and get curious about why

[37:17] - AI should be seen as a coworker, not a competitor - the key is training our uniquely human aspects: emotional intelligence, sense-making, and asking better questions

[39:38] - First step to building human infrastructure: Create psychological safety where people can voice concerns, and reconnect with your company's core mission and values

"Most teams learn the hard way: Technology rarely fails because of the tools. It fails because the people aren't aligned to use them." - Barbara Wittmann

"If your company is not really talking to each other as it is, a software is not gonna fix the issue." - Barbara Wittmann

"We are upgrading servers all along, but with people upgrades, we look at it in a very old fashioned way. It's a one and done kind of thing." - Barbara Wittmann

"AI models are evolving at the speed of light, and we are not upgrading our humans. What can go wrong?"- Barbara Wittmann

"Your execution layer cannot delegate complexity anymore because they need to deal with it inevitably."...

In this episode, Jeff Mains sits down with Michael Ferranti, a veteran of developer tools and cloud-native infrastructure with over a decade of experience at companies like PortWorks, Teleport, and Unleash. Michael shares insights on feature management, the critical role of feature flags in modern software delivery, and how to effectively market to developers.

The conversation explores why "friends don't let friends build their own feature flag system," the evolving landscape of product-led growth, and how AI is reshaping go-to-market strategies for developer tools.

[5:27] - The Common Thread in Category Creation

[7:17] - What is Feature Management?

[11:56] - The Cost of Downtime

[18:28] - The Race Car Analogy

[19:59] - Marketing to Developers

[24:18] - User vs. Buyer

[30:30] - Easy to Try is Essential

[35:30] - Organic Search is Declining

[36:29] - AIO (AI Optimization)

[40:26] - The PLG Myth

[44:17] - The AI Shift

1. Market Size Trumps Perfect Execution Even with the best product and conversion rates, growth will plateau if your addressable market isn't large enough. Evaluate market size as rigorously as you evaluate product-market fit.

2. Speed Requires Safety Mechanisms The fastest-moving teams aren't reckless—they've invested in systems (like feature flags) that allow them to ship confidently and recover instantly. Build your "brakes" before you try to accelerate.

3. Know Your User vs. Your Buyer Developer tools require a dual strategy: serve the hands-on-keyboard users who will love (or hate) your product, while convincing budget holders of business value. Neglect either and you'll struggle.

4. Friction is the Enemy of Adoption In developer tools, the ability to try your product without a sales conversation isn't optional—it's existential. Whether through open source, free trials, or freemium models, eliminate barriers to first value.

5. Proprietary Data is Your AI Moat As AI reshapes discovery, the companies that win will be those with unique data sources that LLMs cite as authoritative. Think "Zillow for home prices" in your category.

6. Adaptability is the New Competitive Advantage The pace of change has accelerated to the point where strategies have a 3-6 month shelf life. Build a culture of curiosity, experimentation, and rapid learning rather...

In this episode, Jeff Mains sits down with Martin Lesperance, an engagement specialist and interactive keynote speaker on a mission to help people fall back in love with their work. Martin shares his powerful "Four Not So Surprising Secrets" framework for rebuilding engagement, motivation, and momentum in the workplace.

From the symbolism of the yellow smiley ball to practical strategies for combating the engagement crisis (which is now worse than during the pandemic), this conversation offers a refreshingly human approach to leadership. Martin explains why engagement isn't a soft skill—it's strategic, and why bringing energy back to work starts with purpose, presence, gratitude, and fun.

5:18 - The Yellow Ball Philosophy

8:07 - The Founder Roller Coaster

11:39 - The Engagement Crisis

13:41 - Secret #1: Live Your Why

17:32 - Finding Your Why

22:32 - Secret #2: Be Present

24:00 - The Smartphone Problem

27:17 - Secret #3: Be Grateful

31:17 - Wabi-Sabi: Beauty in Imperfection

36:00 - Secret #4: Have Fun

39:34 - The Seattle Fish Market Example

41:50 - Making Dreams Come True

45:15 - Remote Engagement Challenges

When people stop caring, performance doesn't crash loudly—it quietly leaks out through missed details, slower execution, and "good enough" energy. With engagement at an all-time low (worse than the pandemic), leaders must treat engagement as strategically as they treat revenue metrics.

Your "why" isn't about you—it's about who you serve. When teams realize they're serving others (customers, colleagues, end users), the grind becomes meaningful. Help your team answer: Who do we serve? How do we serve them? What makes us proud?

In a world of Slack threads, Zoom boxes, and endless mental tabs, attention has become one of the rarest leadership skills. Listen to understand, not just to respond. Put down the devices. Be fully there. Someone on your team deserves more of you.