Build a Business That Thrives on Its Own.

Discover the Next Peak of Your Leadership

A transformational journey for CEOs: 3 months of deep coaching

+ 2 weeks of once-in-a-lifetime experience.

The New Zealand Challenge: Leadership, Liberation, and Legacy

You didn't build your company just to feel trapped by it. This program is for CEOs who are ready to create a business that thrives without them—and to rediscover what comes next.

It's not a retreat.

It's a RESET.

For your business. For your leadership. For your life.

In the New Zealand Challenge,

you'll go through two powerful chapters:

CHAPTER 1: Rebuild Your Business

With 3 months of one-on-one and group coaching, you'll shape a stronger, more independent leadership team that allow you to focus on what matters most.

CHAPTER 2: Rediscover Yourself

In a once-in-a-lifetime adventure through New Zealand's wildest beauty, you'll explore your next personal and professional summit.

This Is Not for Everyone. But It Might Be for You.

You're not afraid of getting your boots dirty and your heart stirred. This is for those who dare to dream.

You Are:

A CEO of a growing company with 10–500 employees.
Feeling like the bottleneck in your own business.
Tired of pushing every project, every person, every deadline.
Longing for time, clarity, and the ability to step back without fear.
An adventurer who wants to hike one of the best walks in the world

You Want:

A self-driven leadership team you can trust.
Systems that run without your daily handholding.
A life with space for reflection, adventure, and meaning.
To feel free—again

Chapter One: Build a Company That Doesn't

Need You Every Minute

By the end of this chapter, you'll have an organisation that runs with or without you—and a mind that's ready for the second chapter. For 3 months, you'll receive:

A Game Plan for Scale

A custom roadmap to delegate, simplify, and empower

Unlimited 1:1 Coaching

Focused on leadership, systems, team design, and personal bottlenecks

Real Accountability

No fluff. Just results. We track progress and maintain focus

Weekly Group Masterminds

Connect with other CEOs in the Challenge for shared insights

Chapter Two: Go Off the Grid.

And Come Back Changed.

Chapter Two: Go Off the Grid. And Come Back Changed.

For two weeks, we'll hike, pause, reflect, and grow—together.

Guided Treks

Experience some of New Zealand's most breathtaking Great Walks with expert guides.

Campfire Sessions

Share deep conversations under the stars about legacy, purpose, and direction.

Coaching in Motion

Experience deep conversations on trails, at summits, and by glacial lakes.

Break Patterns

Step away from your routine to meet your next version and discover new perspectives.

This isn't tourism. It's transformation. You'll leave with a stronger body, a sharper mind, and a clearer mission for what's next.

This isn't tourism. It's transformation. You'll leave with a stronger body,

a sharper mind, and a clearer mission for what's next.

Meet Your Guide & Coach – Gilad Wagner

As a seasoned leadership coach with over 20 years of experience working with CEOs and executives, I've witnessed firsthand the challenges of building a company that can thrive without constant intervention.

My background combines business leadership and transformational coaching, with experience as an officer in the special forces, where I led teams all over the world in missions, workshops, programs, and journeys. This unique perspective gives me insight into both the organizational and personal aspects of CEO growth.

I created the New Zealand Challenge to combine my love for adventure and the outdoors with the organizational adventure of leadership transformation. After seeing how many leaders are trapped by their own success, I knew there had to be a better way.

Building my company, Milestone, to work independently allowed me to pursue my dream of relocating to New Zealand. My coaching philosophy centers on creating sustainable systems, developing leadership teams, and helping CEOs rediscover their sense of purpose beyond the day-to-day demands of their business.

What Past Participants Say

Hear from CEOs who have already taken the Challenge

"I wasn't just skeptical about coaching—I was negative toward the whole idea. I used to think—what can an external person really offer me? How could they possibly understand the reality of my day-to-day leadership? But today, after these sessions, I regret not doing this five years ago! The value of having an external person who challenges you and helps you become better—it's just enormous. It made me think deeply, question assumptions, and after each session, it took me 24 hours to digest things—and then I went out and applied them. I felt you enriched my life, my work, and helped me grow. It was incredibly valuable—and I really enjoyed it. A big thank you!"

Marcel Martens

GM EMEA HP

"Gilad was able to quickly and precisely identify my company's growing pains – and more importantly, the ways in which I was unintentionally holding it back. The entire process was clear, structured, and full of real progress. Gilad brings a rare combination of deep business experience, high-level managerial insight, sharp analytical skills, and an exceptional ability to diagnose challenges and offer powerful, practical solutions. What mattered most to me was receiving real, actionable tools – not empty buzzwords – and I found myself implementing them already during the program."

CEO O.G.A

"When I joined the Challenge, I was in a very critical and intense period, with many important things coming together all at once. I felt alone in my role as CEO. Joining was an opportunity to speak with someone who truly understands the complexity, and who helped me plan the most sensitive and high-stakes matters I was facing. In a very clear and structured way—and through a fast, low-effort process—I gained clarity on what really matters and how to execute it. I immediately began implementing changes, even during the Challenge itself. I highly recommend the CEO Challenge."

Gadi Konvalina

CEO, Feelit

"In this challenge, I had to introspect and reevaluate the various aspects of change, including people, strategy, and processes. We've started thinking about this cycle before, but with Gilad, it was a very clear picture. Gilad's ability to offer realistic, penetrating observations made me delve deeper and deeper. It generated a process that combined company-level thinking with personal-level thinking. I highly recommend this short intervention, which lead to a meaningful growth opportunity."