Love Your Career Podcast: ​Reflections by Dean Pendergreast on the Journey of Enrolmy

About the Love Your Career Podcast and Host Lawrence Everest

​Lawrence Everest is the CEO and co-founder of Love Recruitment (2015) and Love Childcare Recruitment (2021). He hosts the Love Your Career Podcast, where he interviews industry leaders to share practical guidance on hiring, leadership, and career progression—helping employers build stronger teams and helping professionals grow with confidence.

​I was in the UK on a flying visit when Lawrence from managed to grab me for an episode. I hadn't planned it. But I sat down, and for the better part of an hour we talked through how I'd ended up where I am, and somewhere in that conversation, a few things became clearer than they'd ever been.

That tends to be what good questions do for you.

Starting in the Countryside

I grew up in rural New Zealand. Farm work, rugby, the kind of upbringing that teaches you to get on with things without much ceremony. My formative years in the countryside really shaped the work ethic and values that I still lead with today. After my dreams of becoming one of New Zealand's national rugby players for the All Black's were derailed with a dislocated lumber spine injury, I followed another skillset and became a school teacher. Which I loved, but I also knew that in the long-run becoming a school principal wasn't for me.

I founded MusiqHub while I was teaching and somewhere along the way I ended up earning more from a couple guitar lessons than from a full day in the classroom. I set off down the path of building Musiqhub full time and eventually grew it to over forty locations. And then the software we built to run it became Enrolmy.

It doesn't sound particularly complicated when you say it like that. But none of it was planned. And sitting down with Lawrence, being asked, really asked, how it happened, forced me to reflect on what was intentional, what was me, what was the people around me and which parts were luck.

Having a Solutions Attitude

I believe in bringing solutions. To any and every situation.

There was a point where it was no longer feasible for me to run Musiqhub alongside my full-time teaching gig. The solution was scary but clear to me and my wife, its time to go all in. So I did. Identifying problems and moving fast to solve the issue is one of the reasons why I think I've seen many successes with Enrolmy. Bringing solutions and pivoting quickly.

There have been times when investors have said no.

So we've found another.

There have been numerous moments where the penny has dropped and the Enrolmy co-founders and I have realised, we're on the wrong path and we need to change. We've built and then dropped features because in the end, it didn't hit. We've tried launching products to various markets or even countries and pulled it back too.

It's not been a perfectly linear path to building Enrolmy, but now we're helping thousands of school aged childcare operators around the globe!

Intentionally Building a Team and Culture

Right from building up my trusted team of music teachers, to now hiring Enrolmy staff globally. Choosing people who align with our goals, values and how we outwork these is, I believe, a significant factor to success. I believe in hiring leaders. Enrolmy is a flat organisation structure where team members are encouraged to challenge ideas and provide feedback. Even our interns or newest employees are hired with their leadership potential in mind, as those who take ownership, give and take constructive criticism and love to learn are a vital part to our culture.

Lawrence and I also talked about being wrong. This is one I’ve had to humbly keep learning but has largely contributed to the development of leaders around me.

When you're building a company there's a real temptation to perform certainty, to project confidence even when you don't have it, because you think that's what leadership looks like. What I've found, slowly, is that the opposite tends to be true. The teams I've seen perform best are the ones where anyone, including the newest person in the room, feels comfortable saying "I think we've got this wrong." That culture doesn't appear on its own. It has to be modelled. It has to start with the person at the top being willing to say it first.

My co-founders Mike and Andrew would tell you there have been no shortage of times I've needed to be challenged. We're friends in business because we're not afraid to call each other out. That's not always comfortable. But I think it's essential.

The Role of Luck and Opportunity

​I had a good starting point in life. A solid upbringing, decent education, the kind of foundation that gives you options. I'm aware that not everyone has that, and I don't pretend otherwise. But here's what I said to Lawrence, and I meant it: that foundation doesn't do the work for you.

The people I've seen fail with every advantage tend to be the ones who thought the world owed them something. The ones I've seen build remarkable things, often from much less, tend to be the ones who believed they owed the world something. That's not a small distinction. It shapes how you show up every day, whether you're waiting for the opportunity or already doing the work so you're ready when it arrives. Now there have been plenty of moments where doors have opened or opportune emails or phone calls came out of the blue, but you've still got to do that work to be in the position to handle those opportunities and see them through.

Growing up on a farm, nobody confused hard work with luck. You got up because the work was there, not because someone was watching. That instinct, show up, do the thing, figure it out, is probably the most transferable thing I took into building a business.

Podcast Reflection

I'm glad Lawrence grabbed me that afternoon. Not because I said anything particularly new, most of it I'd been thinking for years, but because saying it out loud, in order, to someone asking the right questions, has a clarifying effect. You discover what you actually believe when you have to articulate it.

If you're building something in childcare, kids' activities, or education, if you're somewhere in the uncertain middle of it, I'd encourage you to listen. Not for my story specifically, but for the reminder that most careers don't go to plan, and that's rarely the problem we think it is.

Listen to the full episode on Spotify (55 mins)