Cheryl Spain is a Leading Change for Good Alumni

What if giving wasn't just a transaction, but a relationship built on trust?

That's the question that kept surfacing as we spoke with Cheryl Spain, a graduate of the Leading Change for Good programme at academyEX and executive director of The Gift Trust. With more than 25 years working in philanthropy, social justice, and environmental change across New Zealand and the UK, Cheryl has spent her career shaping generosity into impact.

But it was during a time of rapid growth within The Gift Trust that she chose to step back, reflect, and reimagine her leadership.

The Challenge: Scaling Values

In 2021, Cheryl had been leading The Gift Trust for four years. It was growing quickly. What had started as a small, nimble team was evolving into a complex operation supporting millions in giving.

"We were about to grow fast, and I knew we needed strong foundations," she says. "But I also needed inspiration. And I didn't want to lead the way I'd always led."

So she enrolled in Leading Change for Good, a programme designed to strengthen values-based leadership and connect changemakers across sectors. What she found was a cohort of people as curious, ambitious, and generous as the communities they served.

The Turning Point: Personal Meets Professional

For someone who had long focused on organisational outcomes, the course offered a surprising provocation: to reconnect with her why.

"I've always had a strong sense of why I work in this space, but I hadn't really articulated it. The course helped me name my why and understand how my own journey shaped my leadership."

That journey included growing up in a large family with a solo mum in a lower-income part of Wellington, followed by a sudden shift to a much wealthier environment when her mother became a housekeeper in a well-off household.

"I saw two very different worlds. And I realised how much of life comes down to luck—and how powerful it is when people choose to give back."

That lived experience became the foundation for Cheryl's commitment to equity in giving.

The Transformation: From Admin to Action

Through the programme, Cheryl sharpened her strategic thinking, embedded kaupapa Māori more intentionally into The Gift Trust's mahi, and co-created new initiatives like the Gift Collective. This fund-holding model enables small, grassroots organisations to thrive without administrative burden.

"We've raised over $5 million through Gift Collective already. Many of these groups are kaupapa Māori-led. We act as their financial back end so they can focus on what they do best."

Alongside that, she's helped The Gift Trust distribute over $110 million to causes that matter, with sharp awareness of the power dynamics at play.

Watch this webinar on our YouTube channel

When Giving Gets Complicated, Start with Trust