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From law to life: Tom Kaldor

Tom shares a career shaped by innovation, entrepreneurship and rethinking the future of legal services.

29 May 2026

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Tom Kaldor graduated from Sydney Law School in 2011 before embarking on a career across some of Australia’s leading legal institutions, including the Supreme Court of New South Wales, Allens and the High Court of Australia. Over the course of his professional journey, he transitioned from traditional legal practice into the startup and technology space, ultimately founding Ajust, an AI-powered platform helping consumers resolve disputes with businesses. We sat down with Tom to chat about his experience.

What’s your favourite memory from your time at Sydney Law School?

Hanging out on the steps outside the Law School library, writing skits for the Law Revue. I did the Law Revue for 4 years and was the director in 2010. From that experience, I made relationships that are still some of the most important in my life today – including my wife, close friends and collaborators at Ajust.

How did you get started in your legal career?

I started at the same place as a lot of Sydney Law School graduates: a summer clerkship at a corporate law firm (Allens). But Allens wasn’t my first full-time legal job after graduation. That came up a little differently. I did my final semester of uni on exchange in Copenhagen (an amazing experience). I was planning to spend the next year travelling, but there were also some pretty good reasons to come home. As I was thinking through that decision, a Professor I knew from Law School emailed me about an opportunity to work as a researcher for the Equity Division of the NSW Supreme Court. I took it as a sign to come home and ended up in the role. (But I still had to travel for a good stretch before the job started!)

Can you give us a brief snapshot of your career journey from graduation to now?

I started my career working in blue ribbon legal institutions: the Supreme Court of NSW, Allens and then the High Court (as an associate to Justice Kiefel, a few years before she became Chief Justice). After the High Court, I was due back at Allens – but in my heart I knew I wanted a different path. I was brave enough to try something new, but not brave enough to leave the law completely. Luckily, I stumbled across LegalVision, which at the time was a young business in the emerging NewLaw sector. LegalVision introduced me to a version of law that was genuinely different. It was also my cadetship in building a business, giving me the experience and confidence to take the leap into my own startup, which is not a legal business, but still has some connections to the world of law.
 

Know yourself - the legal profession has a strong pull towards precedent and conformity; hold onto what makes you ‘you’.

Tom Kaldor

Class of 2011 Bachelor of Arts (Honours I, University Medal), Bachelor of Laws (Honours I)

What’s one thing you love about the work you’re doing now?

I run Ajust – our AI agent takes on cases for consumers when things go wrong with businesses. The agent can send emails, complete web forms and engage in live chat to help consumers get a fair outcome for issues like faulty products, slow internet, unexpected bills and cancelled flights. I love how tangible our work is: it’s so validating to see consumers using Ajust and getting real results every day. Plus, we’re living through a seismic change with AI right now – and I feel lucky to be in a role where we constantly use this technology in both our product and our business operations.

What’s your top tip for current law students?

First, work with a business (and with people) you actually believe in – whatever it is, it should be something you’re proud to talk about at a barbecue. Next, be willing to reinvent wheels – there’s almost always a different and better way of doing things. Lawyers have many of the skills you need to create new paths, as long as we’re willing to ask the difficult questions. Finally, know yourself – the legal profession has a strong pull towards precedent and conformity; hold onto what makes you “you”.
 

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