Looking for an executive role in New Zealand is nothing like looking for a senior one. The market is smaller, the rules are unwritten, and most of what decides outcomes happens in rooms you're not in.

In this solo episode, Jakub shares three big ideas that reframed how he thought about the exec search, the small things that quietly make or break processes, and what to remember when it doesn't go your way.

This episode is sponsored by Wires Uncrossed.

After three years, Joekub is back, and this time they brought a startup, an AI agent that writes project updates in five minutes, and some very uncomfortable questions about your career trajectory.

Jakub and Joe (collectively: Joekub) reunite on Tech Waka for a wide-ranging conversation about what's actually happening at the coalface of AI-powered delivery. Joe left agile coaching to join an AI startup and hasn't looked back. Jakub is steering product and technology through the same wave from the C-suite. Between them, they've got enough delivery scar tissue to know when something is new and different.

They cover why extreme programming turned out to be a prophecy rather than a methodology. Why the spec is more important than the code now. Why your AI agent might be sandbagging its own performance to protect team morale. And the question that no one in a sprint planning meeting wants to answer out loud: if the agent is outperforming the humans, who gets the bonus?

Funny, honest, and grounded in real experience, this is what it sounds like when two people who've been around long enough to have opinions stop being polite about AI and just say what they think.

This episode is sponsored by Wires Uncrossed.

JD Trask has been building global tech companies from Wellington since 2007, first Mindscape, then Raygun, now Autohive. When ChatGPT arrived, he didn't wait to see what happened. He shut down his company for a week, made every employee pass an engineering hiring test using AI, and started rebuilding his entire organisation around agents.

In this episode, JD shares what he actually saw during that week, why he put TVs around the office showing each employee's token usage, and why he thinks the "AI makes mistakes" argument says more about the person making it than about AI. He also shares his AI economic maturity model, his take on headcount as an ego metric, and why the most important thing a CEO can do right now is get their hands dirty.

Autohive: https://www.autohive.com/

Raygun: https://raygun.com/

This episode is sponsored by Wires Uncrossed - helping teams across New Zealand, Australia and beyond untangle software delivery and build systems that truly perform. wiresuncrossed.co.nz

Lauren Peate and her team at Multitudes spent 15 months researching how AI is actually impacting engineering teams, following 500+ developers, surveying hundreds of leaders, and conducting in-depth interviews.

What they found challenges the hype: engineers merged 27% more PRs after AI rollouts, but also did 20% more out-of-hours work. The biggest predictor of success wasn't the tool , but it was leadership.

In this episode, we dig into what separates successful AI rollouts from struggling ones, why peer-to-peer learning matters more than mandates, and what engineering leaders should actually be measuring.

Get access to Lauren's research here: https://www.multitudes.com/research

This episode is sponsored by Wires Uncrossed.

Daniel Walters is a consultant, CTO coach, and former CTO of Seek Asia - one of Southeast Asia's largest job platforms. He is the founder of Great CTO, where he works with technology executives across New Zealand and beyond. He is also the co-creator of an AI-assisted engineering course, now running its eighth cohort.

In this episode, we cover:

• What drew Daniel from the operator role into coaching and consulting
• How he defines the difference between coaching, mentoring, and consulting, and why it matters
• The most common themes that come up when CTOs seek coaching support
• Why experienced engineers often resist AI adoption, and how leaders can bridge that gap
• The origin of the AI-assisted engineering course and what they have learned building it
• Why a cohort-based, experiential format is the right container for this kind of learning

Links

• Daniel's website
• AI-assisted engineering course

Why are your teams busy, but the business isn't growing the way it should? Sarah Clearwater, founder of Reframer and customer experience strategist, explains how siloed KPIs create invisible dysfunction — marketing optimises for volume, sales for conversion, product for features, and engineering for delivery — while nobody is optimising for the customer journey as a whole.

In this episode, we explore how customer journey mapping gives technology leaders a shared language for prioritisation, why engineers benefit from seeing how their work connects to real customer value, what "experience debt" is and why it might be the best way to get your executive team to care about tech debt, and how AI agents are changing journey design.

Try it yourself: download Sarah's free 90-minute journey mapping template at https://www.reframr.co.nz/90minutemap

This episode is sponsored by Wires Uncrossed.

Sometimes it feels like senior leadership in New Zealand tech isn’t recognised at the level it should be , especially when big roles come up, and decision-makers look offshore for “proven experience”.

In this episode, Jakub is joined by Paul Meyrick and Stuart Collins from Wires Uncrossed to unpack what’s really going on. Drawing on leadership experience across Silverstripe, MetService, BNZ, and Xero, they explore the hidden step-change from being an excellent engineer to becoming a system leader — shifting from “building solutions” to “designing the conditions where solutions can happen repeatedly”.

They talk about why success feels harder to claim in leadership, how humility can turn into invisibility, and why the right language matters when you’re asking for investment or influencing boards and exec teams. They also share practical signals that you’re ready for the next step, how to make imposter syndrome work for you (without letting it crush you), and why community and mentorship are critical — because leadership can be lonely.

In this episode we cover:

• Why NZ tech leadership can be under-recognised (and what to do about it)

• The shift from technical leader to system leader

• Visibility vs humility: claiming impact without ego

• How to build the language to influence senior stakeholders

• Signals you’re ready for the next step in leadership

• Community, mentorship, and frameworks that help when leadership feels lonely

This episode is sponsored by Wires Uncrossed.

This episode is a little different. Instead of a guest, I’m taking a moment to reflect on Tech Waka’s second year — and how it grew from a podcast into a community for New Zealand tech leaders.

This episode is sponsored by Wires Uncrossed.