Endeavor Founder Stories | Episode 4: Kirsty Chadwick, Founder & CEO of TTRO

The Unconventional Origin: From Piano to Property

Kirsty’s journey started on a dairy farm in Taranaki, New Zealand, where she learned the value of hard work and “grafting” as part of the family workforce. Her initial dream was unconventional: to be a concert pianist, a path that was abruptly ended in her second year of university after cutting her fingers in a lawn mower.

This setback led her to teaching, a natural fit given her love for school. However, a move to the UK for her two-year “OE” (Overseas Experience) quickly showed her that the classroom was no longer her fit. She found surprising success in a commission-only, door-to-door sales job:

“For some reason, I was really good at that. I made more money doing that than I made as a teacher in the UK.”

This discovery of her commercial strength ultimately led her to become a financial advisor and set up a mortgage brokerage—her very first entrepreneurial venture.

The TTRO Foundation: Solving South Africa’s Skills Gap

Kirsty’s move to South Africa sparked the vision for TTRO. She was deeply moved by the gap between credentials and practical skills while recruiting for her contact center:

“The level of education that some of the youngsters were coming with… they really didn’t have the skill that was needed in order to get them into that opportunity.”

TTRO was born in 2008, fueled by a passion to fundamentally change people’s lives through transformative learning experiences. This passion remains the core of the business, proving that for service-driven, people-centric industries like education, an emotional connection is a powerful driver.

Global Impact and The Power of Trust

TTRO’s global expansion into the Middle East, particularly Saudi Arabia, proved the need for localization and built upon a strong foundation of trust.

Rather than developing content from South Africa, TTRO proposed a unique model: they would empower young Saudi women with the skills to be the creators of digital learning content for their own nation. This initiative was a significant contribution to Vision 2030, setting the stage for how educational technology would evolve in the Kingdom.

The Pain of Transformation: Shifting to High Performance

The last few years, post-COVID-19, presented significant headwinds for TTRO, leading to necessary but painful rounds of restructuring and retrenchments. Kirsty realized her business needed a complete culture overhaul:

“I had to change the entire culture of my business. I needed to shift the culture from being a more family oriented culture to being a high one of high performance.”

This required establishing a new operating model, ruthlessly focusing on efficiency, and making difficult decisions around performance management that she had delayed. There were moments of self-doubt, but her intrinsic nature—”I’m not good at quitting”—forced her to push through, transforming the business into a structure ready to compete globally.

Leadership and the Power of Network

Kirsty advocates for finding the right balance between leading (setting culture and strategic direction) and managing (ensuring day-to-day performance). She also maintains an open view on the CEO role, noting that after 17 years, bringing in new skills and different experiences may be the right path for the business’s next chapter.

She stresses the critical importance of having a trusted network like Endeavor: “It’s not your family. It’s not your staff… it’s a network of just trust where you can truly be vulnerable.” This network provides the comfort and perspective needed to overcome the often lonely journey of high-impact entrepreneurship.