“I swore I’d never be CEO” and how Dale Clareburt built a global HR tech company anyway

Boxers & Briefs Podcast #20: Building Resilience with Dale Clareburt

When Dale Clareburt co-founded Weirdly in 2014, she made a declaration to her fellow founders: “I don’t mind what happens so long as I’m not the CEO and I don’t end up in this business on my own.” Six months later, she was the CEO. It’s just one of many examples of how entrepreneurship can take you to unexpected places – often the very places you swore you’d never go.

As the co-founder and CEO of Weirdly, an HR tech platform that helps match candidates with company cultures, Dale has spent the past decade navigating the exhilarating, terrifying, and sometimes lonely journey of building a tech startup. From early morning gym sessions to pitching to Facebook and McDonald’s with a team of just six people, her story reveals what it really takes to build a resilient business – and yourself along with it.

The untold CV: finding the person behind the paper

Weirdly was born from Dale’s 25 years of experience in recruitment and a simple frustration: CVs only tell a fraction of someone’s story.

“When people are interviewing candidates, they look at a CV or a resume as a representation of a person, and it’s not… it’s not the whole person,” Dale explains. “It just seems a shame that there isn’t a little bit more information about someone so they can showcase themselves a bit more.“

This gap in the recruitment process became especially apparent when working with small businesses like Jucy Rentals, whose founder Tim challenged Dale: “If you could build me a product that would help mitigate the risk of me getting someone who wasn’t aligned with my purpose and values, then I would buy it.“

The result was a culture-fit quiz assessment that evaluated how well applicants aligned with an organisation’s specific values and purpose. But this was just the beginning. What started as a tool to help small businesses quickly evolved into something much bigger.

Like many startups, Weirdly’s journey involved significant pivots. Those first few years were spent experimenting – trying different pricing models, refining the product, and searching for product-market fit.

The breakthrough came when they realigned their focus from small businesses to large enterprises. “We realised that our product worked best when it was able to be used hundreds of thousands of times rather than just thousands,” Dale says. “We went from doing 1 to 8,000 [assessments] per client a year to 500,000 with one customer.“

This massive scale-up led to expanded capabilities. What began as a culture assessment tool evolved to encompass the entire early recruitment process, from application to interview booking. The efficiencies they created for their clients were immediate and substantial, helping Weirdly secure capital for further expansion.

“You have to be brave” taking New Zealand to the world stage

Dale’s entrepreneurial journey has taken her far beyond New Zealand’s shores. In 2016, with just six employees, she embarked on an ambitious trip to the United States, meeting with tech giants like Facebook, Google, and PayPal.

“It was a massive leap, but that’s what you’ve got to do,” she reflects. “You’ve got to be brave. You’ve got to go over there, you’ve got to go to all the networking events, you’ve got to walk up to people and introduce yourself.“

The experience taught her about cultural differences in business approaches. American meetings were direct and efficient: “You walk into a meeting and it starts with ‘They have a hard stop in 25 minutes, what can I do for you?’ That’s how it works… you can do 10 meetings in a day.“

Though the US expansion didn’t materialise as planned (largely due to insufficient capital), Weirdly later found success in the UK market. Just before Covid hit, Dale and her team flew to the UK for what would be one of the last flights back to New Zealand before border closures. The gamble paid off – they beat local competitors and secured Vodafone Global as a client.

She credits New Zealand’s business style for their overseas success: “We’re really good. Kiwis are fantastic in presentations. We’re enthusiastic, we’re grateful to be there… We don’t rock up in suits… we’re very casual but engaging and authentic, and people love that.“

“We give away too much of our business early on.”

When asked about lessons from her entrepreneurial journey, Dale doesn’t hesitate to discuss funding strategy – specifically what she might have done differently.

“The reason I wish we’d bootstrapped for longer is because when we first started… we gave away too much of our business early on in return for capital,” she explains. While grateful for her investors (PAII and 2040 Ventures), she acknowledges, “We didn’t think carefully about the long-term of every time we raise capital, we lose a little bit more.“

This creates two significant issues. First, founders can become demotivated as their ownership stake diminishes. Second, and perhaps more crucially, a fragmented cap table (ownership structure) can become problematic when seeking larger funding rounds later.

“When you start to get to a point where you want to raise big money… the people that write those checks are a different kind of investor sometimes, and they look at your cap table. If your cap table is a little bit messy, like there’s too many people who have ownership or shares, then that can be unappealing to potential investors in the future.“

Dale believes even bootstrapping for just 6-12 more months might have made a significant difference, allowing them to learn expensive lessons on their own dime rather than investors’.

The false economy of solo travel

Among Dale’s most interesting reflections is her assessment of how she approached international business travel. Driven by New Zealand’s frugal business culture, she always opted for economy seats and budget accommodation like youth hostels when travelling.

While the cost-saving approach seemed sensible at the time, she now sees a hidden cost: “I did that and I went alone, and I think that it’s a wasted opportunity when you’re going somewhere to really important meetings… Having someone else’s point of view in those meetings – I might have missed an opportunity, I might have missed something.“

She envies other founders who travelled in pairs, who could debrief after meetings and events, provide feedback to each other, and process information together. This collaborative approach might have accelerated their learning curve and improved decision-making.

“I would do differently next time – still economy, but take someone with you,” she concludes.

Cash flow, companionship, and self-care

When asked about her top three priorities for business owners, Dale’s answers reflect hard-won wisdom:

First and foremost: cash flow. “If you can have a runway or you’ve got enough money covering your costs and you’re profitable, then the decisions that you make about the future are better,” she emphasises. “You’re thinking about it from an innovation and staying true to your values and your brand… rather than saying yes to any money that can walk in the door.“

Her second priority is never going it alone. While four co-founders might have seemed excessive to some advisors, Dale found strength in numbers. “I’d say you need at least two because it’s a very lonely path,” she says. “Having worked in senior roles inside smaller businesses, I thought I knew what it meant, but it’s not the same as owning your own business.” Beyond distributing the burden of responsibility, she adds, “It’s lots more fun to do it with somebody else.“

Her third priority is perhaps the most personal: putting yourself first. After nearly burning out, Dale now prioritises her health with non-negotiable early morning gym sessions starting at 4:15 am – a time when no one can interrupt her.

“In the past, I would put everything… I would put work first always, and as a result, I nearly burned out,” she reflects. “You’ve got to understand this is a marathon, it’s not a sprint, and you’ve got to look after yourself.“

Building resilience through repeated exposure to fear

What gave Dale the resilience to keep going through a decade of business challenges? Part of it came from her upbringing – “hard work trumps everything” – and a natural tenacity. But she also developed a philosophy of purposely seeking out challenges.

“Repeatedly doing things that scare you builds resilience,” she explains. Whether it was travelling alone to unfamiliar cities, pitching to rooms full of strangers, or facing the prospect of missing payroll, Dale found that the first experience was terrifying, but each subsequent iteration became easier.

“In a startup, in your own business, you’re doing that every single day, and you actually become addicted to it,” she says. “When you don’t have too much to do, or you don’t have something in front of you that might scare you, a challenge or something like that, you can feel bored.“

This mindset has transformed her relationship with fear entirely. Rather than avoiding scary situations, she now seeks them out, believing that “you wouldn’t believe what you’re capable of” once you push through initial discomfort.

The five days when everything clicked

After years of challenges, Weirdly experienced a profound breakthrough last year. In the span of just 3-5 days, several critical elements converged: they expanded from 100 users to 2,000 users through a new feature that allowed hiring managers direct access to their platform; they achieved profitability after years of prioritising growth at all costs; and they demonstrated that their product had appeal beyond the few long-standing customers who had been with them from the beginning.

“We went, ‘This is what it’s supposed to feel like,’” Dale recalls. “We’ve got 2,000 people who love our product using it, we’re profitable now, we’ve got the base that we need to take the next big step, and we’ve got a fantastic team of people.“

This moment of alignment – where product, finances, and market validation all clicked simultaneously – provided a powerful affirmation that the years of persistence had been worthwhile.

The power of ‘can’t’

Perhaps the most revealing insight into Dale’s character comes in her response to being told something isn’t possible: “If someone tells you you can’t do something, then you absolutely must do it.“

This defiant spirit has propelled her through countless obstacles, from scaling a tech business globally to maintaining her own wellbeing during the process. It’s an attitude that has served her well in a journey filled with unexpected turns, including becoming the very CEO she once swore she’d never be.

For entrepreneurs facing their own challenges, Dale’s story offers both practical advice and inspiration. Her willingness to share not just successes but also missteps and course corrections provides a realistic picture of what building a business truly entails – a constant process of growth, adaptation, and pushing beyond perceived limitations.

As she continues to evolve as a founder, Dale carries forward the lessons from building Weirdly, applying them to new ventures with the benefit of experience and the same unyielding determination that has defined her entrepreneurial journey thus far.

This article is proudly brought to you by Gilligan Sheppard, the problem solvers in business who believe in thinking differently.