With more than 15 years' experience in tech spanning three continents, Alison Caldicott, Head of Marketing and Digital at WiseTech Global, has a wealth of knowledge and advice, and is passionate about creating a culture of equality and respect.

In celebration of International Women’s Day, we sat down with Alison to hear about her experiences as a woman in tech, how she overcame imposter syndrome by backing herself, and why we all have a role to play in eliminating gender biases.

How did you get into tech and what’s your experience as a woman in tech been like?

While my background is in marketing and communications, I’ve been working in tech for the last 15 or so years and, overall, it’s been an incredible experience.

But I’m very aware that I kind of fell into the industry, many years ago, when I started my career at a Sydney-based PR agency. At the time, I got to pick between working on a premium skincare range or a global telecommunications client. Despite my friends thinking I was crazy, I picked the latter.

While I’d never seriously considered a career in tech before that, I loved the fast-paced nature of the work and the fact that innovation and entrepreneurship are at the heart of the industry.

I’d like to think I can count on one hand the number of times I’ve been made aware – intentionally or unintentionally – of my gender in the workplace. But there’s no denying those moments do stick with you. The fact is that IT, like many industries, remains male dominated – particularly in technical and more senior positions.

While there is no single solution for this imbalance, I’m pleased that we’re increasingly having conversations focused on the root cause of the problem, not just the symptoms. For example, recent studies revealed some parents’ outdated perceptions of jobs for men and women were in fact discouraging girls from pursuing a future in the STEM sector.

That’s why I’m so inspired by our CEO Richard White’s personal commitment to transform STEM education in Australian high schools, particularly for girls and students from remote areas. Fast forward 10 or so years and I can’t wait to hear about the incredible women running some of Australia’s most successful and innovative tech companies.

What’s an achievement (either at work or outside of work) that you’re proud of?

Probably backing myself when I moved into my current role at WiseTech as Head of Marketing and Digital in early 2021.

In corporate speak, I was an “individual contributor" for a number of years. For normal people, that just means I hadn’t had a lot of experience leading large teams.

This role oversees a sizable global team of deep domain experts across marketing, digital platforms, design and video production, so I was worried my lack of people management experience would be glaringly obvious from the get-go.

I allowed myself to fret about it for a couple of days and then took a friend’s advice to write down all the great things I could bring to the role, including the unique experiences I’d had over the previous five years living and working in the USA and UK.

Sure, I hadn’t managed a large team. But I had done a six-month secondment at an amazing e-health company in London. I’d spent time in San Francisco, working alongside smart people from some of the world’s largest tech companies. I’d even had the opportunity to organize a group of my colleagues to participate in the Women’s March in New York, standing in solidarity with others participating in similar protests worldwide.

And it was through this reflection process I realized that actually, my lived experiences – particularly failures and lessons learnt – were extremely valuable, so I should celebrate instead of downplaying them. There will always be a corporate playbook for career progression, but that’s not necessarily the one you have to follow to be successful.

What advice would you give to women considering a career in tech?

My first piece of advice is to build a small, trusted network – say three or four people – who you can have on speed dial when you need important work advice. Ideally, you’ll align on your core values, but they’ll have diverse career experiences to you and, importantly, a bigger appetite for risk.

When I moved back to Sydney from the USA, I thought my best bet was to get as many people’s opinions as possible on my potential next career move. Do not do that. You will get a thousand different views on what these people would do if they were in your position. But not what is necessarily best or right for you.

My inner circle includes a friend who works overseas in finance, and I was matched with him as part of a corporate mentoring program 10 or so years ago. I might only speak to him once a year, but I trust his counsel implicitly and he’ll always be my go-to when I need a pep talk about taking a risk or discussing anything salary related.

My other big piece of advice – perhaps easier said than done – is to back yourself and always know you have what it takes to achieve your ultimate ambitions.

In my 20s I spent a lot of time alternating between imposter syndrome, a fear of failure, and a sense I should be eternally grateful for any career opportunity that came my way. What a waste of energy.

Life is short, so don’t spend it stressing about what someone in a meeting may or may not think about you! Find a company where you can be yourself, do work that you enjoy and comes naturally to you, and succeed alongside a smart and compassionate bunch of people who inspire you. I promise, these jobs do exist, and I feel pretty lucky to live this every day at WiseTech.

What does International Women’s Day mean to you?

International Women’s Day has always been a special day for me. It’s where we get the chance to pause, reflect on, and celebrate women’s stories and successes.

Over the past few years, it’s also become a really important moment to gauge the progress – or perhaps lack of progress – made on some of the systemic challenges holding women back. Think about critical issues like closing the gender pay gap, investing in childcare reform, or getting more women into the workforce.

In 2022, addressing these issues feels more urgent than ever. There’s so much research telling us that women were hit hardest by the pandemic, particularly those in lower income jobs who experienced decreased employment, working hours, and wages at a higher rate than men.

On top of this, while we won’t know the full impact for some years, data shows that all types of violence against women and girls – particularly domestic violence – has intensified since the outbreak of COVID-19.

These statistics are heartbreaking and a critical reminder why events like International Women’s Day shouldn’t be seen as just a once-a-year “celebration”, or a tick-the-box corporate exercise.

As the inspirational Brittany Higgins reminded us during her recent National Press Club engagement in Canberra: The time for talking is over. We need to ensure that words are matched by actions.  

What does this year’s International Women’s Day theme, Break the Bias, mean to you?

So, I’ve got a good story for you on this. A few years ago, I was at a work dinner in a previous role. I was seated next to a customer who I hadn’t met before, so naturally we were engaged in polite small talk.

A couple of minutes into the discussion, he asked me where I went to school in Sydney. I have always found this a loaded question and pretty irrelevant – whether you’ve just finished or graduated 20 years ago like I did.

I asked him why it mattered. He told me, straight faced, that he wanted to “box me”. Confused, I questioned what he meant. “Where you went to school helps me put you in a box. It tells me things about you,” he said. I was speechless.

Now this is an example of social bias rather than gender bias. But it demonstrates how comfortable some people are in making assumptions about your character, capabilities or intelligence, based on random stereotypes and how you look, speak or behave.

For women in the workplace, this might mean someone wrongly assumes you’re more junior because of your age. Or perhaps a colleague thinks you’re being “aggressive” in a meeting, while your male counterpart in similar circumstances is considered “assertive”.

These biases are not just frustrating – they can be very damaging. And they’re even more acute and harmful for women of color, LGBTQI+ women, and women with disabilities.

Sadly, there’s no one simple solution for eliminating biases. But clearly, we all have a role to play in recognizing and combating them.

For me, this means actively listening to others’ perspectives, leaning into difficult conversations, and holding people and institutions accountable for their words and actions. Ultimately, it’s about treating our differences as a source of knowledge and connection, while pushing for a culture that’s built on equality and respect.