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What it’s like being a trans woman in Australia’s startup ecosystem

Joan Westenberg /

Joan Westenberg

Joan Westenberg. Source: Supplied.

I’ve known I was, and identified as a woman, for so many years I can’t recall the moment of realisation that triggered the original realisation. I have a long track record of avoiding it, and denying it, and refusing to acknowledge the situation.

Not too long ago, I stood up in front of my entire startup, over 40 people, and announced that I was coming out as a transgender woman, and that I was going to transition. It was something I was still getting used to saying out loud, still getting used to articulating, still getting used to owning as mine. If I were making a list, that would rank in the top 10 most terrifying, gut-wrenching moments of my life.

Every set of eyes was on me, and I had been rehearsing a bold speech all day, and in the end, I can’t even remember what came out of my mouth. And then people started clapping. The engineers, the devs, the support team, the sales team, the senior leadership. People came up after and hugged me, they emailed me to say they supported me, and that acceptance meant the world.

I work at a tech startup called Flare, and we build onboarding software used by some of the largest hospitality and retail companies in Australia, and that’s meant we care about people, and how we treat everyone here, and that matters. We’re a diverse crew of people, but I am the first trans person in the company. When I first started, I can remember telling a mate that maybe one day, in the future, perhaps five or so years ahead, I might find myself in a position, in a company, in a stage of my life, where I could transition.

It wasn’t something I thought I could do, right now. It wasn’t something that I thought was even possible, right now.

Not long after I started, I was hanging out with the founders, Dan Cohen and James Windon, and talking politics — I am a huge nerd, and it always comes up — and out of the blue, Dan said to me: ‘You know one of the things that are awful about Australia today? We don’t support transgender people enough’. His POV was that we could, should, had to do more, across the board. I looked at him and said: ‘It’s funny you should say that, Dan. I am transgender and I want to transition’. And they said: ‘What can we do to help?’

Flare helped me change my email address. Change pronouns. Change bathrooms. Change how I dress. Every step of the scary beginning of my long journey ahead started here.

Since then, my experience has been so far from what I had always feared.

The people I work with have loved and supported me. For most people in tech, I am the first transgender woman they’ve ever met.  I’m the first transgender person they’ve met full stop, and it’s a strange thing to experience.

People have so many questions, and those questions can be exhausting, but I answer them. I know they’re asked with a good intention and they’re coming from good people.

The folks in startups who have followed my work and my journey and my track record of working in the tech ecosystem have welcomed me as Joan, with open arms. From the team at Microsoft for Startups, to the folks at Microsoft Ignite who have invited me to speak. From VCs at some of Australia’s top funds to the tech bloggers and writers and journos. People have sent me notes to support me, they’ve reached out to just say hello, and I feel supported and accepted in a way that surprised me.

I’ve not found that my access to opportunities has been limited. I’ve not found that people have lost any faith in my work, based on my identity. I’ve not found that I am ever in a position where I can’t be and live out my identity openly and publicly and with a sense of pride.

That puts me in an incredibly privileged position. For many trans people, the outlook is far bleaker. We have high rates of unemployment, low salary growth, huge levels of prejudice and discrimination, and for many of the people I know, transitioning at work is such a non-option that they can only truly be themselves when they clock off. Tech is a more progressive space, generally, and it’s been very kind to me.

My privilege also extends to my position right now; I don’t know how far my career would have gone if I had transitioned to live as a woman earlier on. I don’t know if I’d have been able to achieve the recognition I’ve had for my blog, my work and my commentary, because I can only assume that presenting and living as a male has given me a much, much easier path. It’s not an easy world out there for women, particularly for women of colour and queer women, and I know that we’re not in a utopia.

When I look at the wider picture for my communities, as women and as transgender people, we’re living through a difficult time for representation. Sexism is rampant in so many areas of tech, and there are hugely problematic statistics about the number of women leading companies, exiting companies, receiving investment, being hired as partner, and generally being allowed to succeed by the gatekeepers in the ecosystem. That’s a global problem, and it’s not one that I know how to solve, that anyone knows how to solve in a quick fix.

It’s a wonderful thing to support an individual trans woman, but there’s a statistical and real divide between that experience and the experience of other women, there’s a lot of work to do and there’s no victory yet.

I’m proud of the startup and tech ecosystem. And if you’re a part of it, you should be proud too. It’s been amazing for me. The folks at Flare, the investors and the people I know have shown so much love. I’m happy, and healthy, and safe.

For the next few years, I’m going to be working through transitioning, and I can’t tell you how good it feels to be able to do that. But I’m also keenly aware that my next opportunity to step up is to find a way to encourage the ecosystem that has supported me to extend that support to every woman, working intersectionally to provide more opportunities, more growth and fewer barriers to entry.

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Joan Westenberg

With a thriving global audience, Joan writes about startup entrepreneurship, transgender activism and innovation. She is a mentor for Microsoft for Startups and the number one Medium blogger in the Asia Pacific Area, with an audience of 120,000.

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