Meet the modern entrepreneur nurturing the next generation of women in business

How Caitlin Iles is redefining entrepreneurialism and helping shape the businesswomen of today and tomorrow with a new mentoring platform. By Michelle Keomany. Feature illustration by Stevie Rodger.

This article originally appeared in The Generation Issue, our June/July edition of Marketing magazine.

Michelle KeomanyCaitlin Iles is someone who’s experienced vastly different industries and roles, and navigated everything that being an entrepreneur can throw at you. When no two days are the same and you

have to be your own accountant, marketing team, salesman, cheer squad and everything in between, you learn a thing or two. According to Matt Ehrlichman, CEO of start-up Porch.com, an entrepreneurial spirit is defined by the following qualities: they are in tune with their passion, always questioning how it can be done better, optimistic about all possibilities, take calculated risks and, above all, they execute. Iles ticks every one of these boxes – twice.

At 15 Iles started a social impact business (backed by her dad), buying failed racehorses and retraining them for other roles o the track. During her time as a model and presenter, Iles made herself useful beyond the role she was being paid to do. She also went on to launch a property investment company in Dubai – without ever visiting the country beforehand.

Iles’ career has been anything but linear. Rather than seek the familiar, she has embraced constant change and learned from every aspect of each experience. Hearing about Iles’ instincts in action you get a picture of why she was so successful in venture capital at Artesian Venture Partners. In the world of financing start-ups and small businesses, the risks are higher, but it can be worth it for the long-term growth potential.

Iles explains why the industry appeals to her overall: “Venture capital is about investing in and supporting the brave mavericks who have the solutions to today’s and tomorrow’s problems, are courageous enough to give it a go and have the stamina to keep going when most people would give up.”

She was brought on to help Artesian find a new approach to identifying projects. “As a venture capital and angel investor I love that we are creating a new industry to buoy our economy and make Australia globally competitive and attractive to foreign investors,” she says.

les is the perfect example of what can be achieved when you find the role or industry that suits not just who you are but what you want to become. In a nutshell, Iles says entrepreneurs are ‘her tribe’. “Like me they are energised by ideas and solving problems,” she says. “I find entrepreneurs inspiring, brave, courageous individuals who are always up to something interesting. I love that they’re different from the crowd and challenge the status quo. They are exciting and always at the heart of innovation that leads to the new life-changing companies and products that we love and make life easier. What’s not to like?”

MK0617 cover generationThe tech and start-up spaces, however, are notorious for their underrepresentation of women. So, as one of only a handful of senior women in venture capital in Australia at the time, Iles was continually approached to be a keynote speaker and asked for advice through LinkedIn. The big question that women always wanted to know was how. This spoke volumes about the lack of support services available to women in business. “There’s a big emphasis on inspiration, but not on how to actually get from A to Z,” Iles says. This planted the seed for what has grown into Xchange, a mentoring platform for women in businesses of all sizes.

“It was a conversation with my life-long hero, Sir Richard Branson, that really gave me the confidence to take the leap and start working on Xchange,” she says. It’s this never-ending determination to execute that makes Xchange truly stand out from the crowd.

Set to be fully launched by the end of the year, and now open for subscriptions, Xchange is an ‘edutainment’ marketplace and platform for women in business who want to accelerate their careers and grow their businesses. Xchange merges inspiration with practicality and is rele- vant for all business backgrounds. Exclusive videos feature some of the world’s best (mostly women) leaders, rising stars, entrepreneurs and educators speaking about their expert subjects and there are courses in key areas helping you to upskill.

It’s designed to make learning entertaining, easy to fit around your schedule and not just another thing on an ever-growing to-do list. Most importantly, Xchange focuses on the steps needed to actually reach your goals – or, as the website says, ‘no more flu , we’re talking results’.

There’s also an important community aspect so that members can support each other through all the ups and downs of navigating their careers, and ask questions without judgement. Iles has specifically designed Xchange to help remove the barriers that usually prevent women from reaching new professional heights. “Removing the hand brake,” is how she puts it.

Above everything, Iles is a realist and doesn’t sugar coat anything – her tone is refreshingly blunt. “It’s just so damn hard and we know it’s so damn hard for anyone who’s an entrepreneur. Ninety percent of start-up founders fail and they’ll fail two or three times.”

She outlines the three things that hold up the glass ceiling for women on top of that: lack of role models, lack of exposure to transplant their experience, and knowledge, mentoring and sponsorship. Xchange addresses all three head-on in an innovative and exciting way. “I think it’s important to learn from anyone who is talented and can help you evolve into a better person or professional,” she says, “no matter their colour, gender, cultural background, age.

“The real value of women learning from other, more experienced, women is that it shows them if she can do it, so can I. Research has continued to show that the lack of women in senior levels of business is not due to a lack of competence, rather a lack of confidence.”

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What’s really exciting about speaking to Iles is that she’s true to her entrepreneurial roots, so she’s all about execution and always going that extra step to make something really successful. For Xchange, things are no different – #3billion- women is her BHAG (Big Hairy Audacious Goal) for the platform. “I want to be able to measure that Xchange has directly or indirectly impacted – one woman, one community at a time – the lives of three billion women globally.”

Iles explains why she’s chosen this as her goal: “The statistics show that women reinvest 90% of their resources into their families and community. Men, in comparison, reinvest around 30% to 40%.”

She continues by clarifying: “This is not man-shaming. Men are exceptionally important in resolving the gender diversity issues that we face globally. But if we want to improve things globally for all of humankind, the statistics say we have to start with women.”

So what are some changes that she would implement now to start to make a difference for women? Iles says she’d start by showcasing, promoting and celebrating women who are already excelling in tech. Some of her examples include Cyan Ta’eed, executive director of Envato, a marketplace and community for creative assets and creative people, Rebekah Campbell, CEO of Hey You!, an ordering and payment app for cafés, Nyree Corby, CEO of Fame and Partners, an online platform for made-to-order custom clothing, Jodie Fox CEO of Shoes of Prey, a custom footwear website, and

Taryn Williams, founder of WINK models, who pre-empted the influencer market and created TheRight.Fit, a digital platform and talent agency in one that makes the process of booking talent easier and more transparent.
“These exceptional business leaders provide great role models in encouraging women to consider a career in tech,” says Iles. She points out that one of the issues we currently face is that female talent isn’t transitioning from traditional business models into the technology space, therefore restricting the pipeline of talent needed to power future economies.

Iles is a big advocate for STEM (Science, Technology, Engineering, Mathematics) subjects to be compulsory for every student through to the end of high school. She’s been challenged on this stance: “While this may appear to be a wild statement, it’s based o the success of one of the world’s leading innovation, start-up, venture capital markets in the world: Israel. I believe we have a responsibility to ensure that our future pipeline of talent is armed with STEM skills that will not only ensure they survive but, more importantly, thrive in tomorrow’s economy.” She thinks this is key to helping to change the culture around tech and ensuring more women will consider it as a real career path.

Iles is all about embracing every facet of a role and not avoiding hard conversations or situations and learning from them in as many ways as she can. She points out that people find taking responsibility for failure hard. “Success, however, has a hundred mothers and fathers. Taking responsibility for failures wins respect and, although it’s hard to do, owning your mistakes ultimately stands you in better stead.”

She goes on to caution against falling into the trap of thinking ‘I’m making this difficult and they’ll find someone else’. “This has never been my experience. My father taught me that people will value you by the value that you place on yourself. If you handle tough conversations respectfully and professionally you will win respect. Tough conversations are an opportunity to step up to the next level, not fall behind.”

One big game changer many industries are already facing is automation. While Iles acknowledges that it will be a challenging time for many individuals, she encourages us to shift our perspectives. “What we’ve seen every time technology has improved the efficiency of an industry, it actually frees up human potential to go to the next step,” she says. “That’s why I’m so interested in tech and the industry: its ability to unlock human potential and solve bigger and more important problems.”

Our conversation wraps up by looking at the current landscape and what’s to come in the near future, and pointing out some stark truths. “Sticking to ‘it’s always been done this way’ is just not going to work in the future,” she says. “We’ve seen it in industries that fail to see they’re being disrupted or those that miss opportunities.

“Things are going to change faster and faster and faster. The average lifespan of a company used to be over 65 years and today it’s less than 20. By 2030 it will be less than 15.”

Instead of being intimidated by the constant change around us, true to Iles’ nature, her advice is to embrace it with both hands. “Our careers are never going to look like what they used to look like. The beauty of that opportunity is you get to reinvent your career and how you work. That’s the exciting part.”

Michelle Keomany is a social/content strategist at DigitasLBi France

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