Go With The Data Flow – How Raymond Sun Turned His Passion Into A Career

Author: Ashleigh Cheuk
Interviewers: Jessica Woodyatt, Tiffany Lu & Ashleigh Cheuk

Raymond Sun, a UTS law alumnus, takes us through his inspiring journey to becoming a Senior Associate at Herbert Smith Freehills Kramer, all while building technology on the side. In this exclusive interview, Raymond sheds light on the technology law space, and shares how he leveraged on opportunities to merge his interests with his career.

Chapter 1: How It All Started

Raymond’s fascination with technology began at a young age. He recalls watching Bob the Builder and Thomas & Friends when he was 5 years old, then subsequently moving on to shows like Astro Boy and Iron Man as he got older. ‘I actually wanted to be an engineer when I grew up,’ he confesses.

In high school, Raymond often played computer games with his friends. This sparked a desire to build his own games from scratch, which led him to pick up coding. It was also around this time when he began to read avidly, taking a particular interest in detective novels. He found that he liked the idea of connecting evidence and information together to uncover the truth, which got him interested in law. This prompted him to take up legal studies in high school, a subject he thoroughly enjoyed.

Chapter 2: Decisions, Decisions

When it came to picking a university course, Raymond found himself at a crossroad. While he still loved engineering and coding, he also had a newfound interest in law. ‘I thought I could make engineering and coding a hobby, but I couldn’t really make law a hobby,’ he says candidly. As such, he opted for a straight law degree, and continued working on coding projects on the side.

Was doing a law double degree not an option back then? Raymond shares that it was. However, the most common combination was Law/Commerce, along with Law/Arts and Law/International Studies. Pre-Covid, there were still many jobs available in traditional legal pathways, and so the legal technology scene did not look particularly promising. As such, Law/Computer Science and Law/IT were not popular choices. Furthermore, wishing to keep his university life simple, Raymond ultimately decided to go with a straight law degree. 

Chapter 3: A Budding Career

During his time at university, Raymond took on a number of part-time gigs. He worked as an office clerk at a barristers’ chambers for a year, where he handled administrative work. When the chambers eventually wound up, Raymond sought work elsewhere, sending in numerous applications for paralegal roles. This was met with limited success, prompting him to switch things up and apply for a media intern position at Lawpath – a legal technology startup – instead. He ended up getting the job, and was tasked with writing blog posts daily. Given the craze with blockchain at the time, he wrote countless articles on the subject.

It was also during this time that Raymond participated in a legal technology hackathon, one of the first of its kind. Within his team, he took on the role of developer, which involved building and putting the prototype application together. The hackathon culminated in a pitch to the judges, and as it turned out, one of the judges was the head of Lawpath - the startup Raymond was interning at!

Having made a big impression, Raymond was offered the role of legal engineer at Lawpath the very next day. In this new role, he helped Lawpath build a document automation platform. After working on that for a few months, Raymond began the process of applying for clerkships.

In his penultimate year, Raymond landed a clerkship at Herbert Smith Freehills Kramer. He was assigned to the firm’s new digital law group, which focused on emerging technologies and growing the digital law space. Raymond also did a secondment to IBM as an engineer, where he coded for a smart legal contract platform.

A day in the life of Raymond. This picture was taken in a Prosple article written by Raymond. Read more here.

Chapter 4: Turning Passion into Profession

Following a successful clerkship at Herbert Smith Freehills Kramer, Raymond was offered a graduate position at the firm. During this time, he did rotations through insolvency, class actions, and finally, TMT. Upon completing the graduate program in September 2021, Raymond decided to settle in TMT as it was closer to technology, his main area of interest. He has been in practice ever since, and was promoted to senior associate in July 2025. 

So, what does a day in his life look like? For Raymond, work tends to start from 9.30am, and can end anytime from 6pm to 2am. ‘I do a lot more overseas work now, across Singapore, China, and Europe, so because of the time zone differences, I tend to work later, but also start later,’ he explains.

In terms of his job scope, Raymond categorises it into ‘three buckets’. ‘The first bucket,’ he says, ‘is your big traditional corporate deals, the big M&A work.’ As a technology lawyer, he supports such deals from an IT and privacy angle. ‘So I’m reviewing IT contracts and also looking at the privacy law issues relating to the deal. I’d say that’s around 10% of what I do now,’ he shares.

The second bucket, advisory, constitutes 70% of his work. Startups and big companies approach him for advice on privacy, IP, online safety, and the likes - basically, ‘any regulatory or legal issue around a particular product,’ he explains. Drafting and reviewing contracts relating to a technological product fall within this bucket too.

This brought him to his final bucket, training and education. ‘So I do a lot of presentations and CPD sessions for clients on tech-related topics, and I do that for clients from Australia, China, Singapore, and Europe,’ he shares. In particular, AI legal issues have become a hot topic in recent years.

‘The ratios are very different every day. Some days I have a big deal, and then that first bucket becomes 90% of my day,’ Raymond clarifies. ‘Some other days it’s purely the second bucket, and I do that for a few weeks. The days differentiate, but these are the three main buckets of work,’ he adds.

Currently, about 50 to 60% of his clients are domestic, while the rest hail from overseas. He clarifies that he does not actually deliver advice overseas as he lacks local qualification. ‘But what I do is, I help the locally qualified lawyer with putting together drafts, advice, and doing a lot of the initial contract reviews. Then, we get that signed off by the locally qualified lawyer to then give to the client,’ he explains.

Chapter 5: techie_ray

Even while his career took off, Raymond continued working on tech development projects. One of his most notable projects is the Global AI Regulation Tracker, an interactive world map that provides users with quick summaries of the AI regulatory approaches and developments in various countries. The idea for this tracker came to him quite organically - he got interested in AI ethics back in university, and made notes in his diary over several years. Eventually, he took to posting on LinkedIn, where he shared about the AI policies in different countries. His LinkedIn posts eventually blew up, and, in a bid to better organise his posts, the Global AI Regulation Tracker was born. Fast forward to today, it now covers more than 200 countries - a highly impressive feat! Besides the tracker, other noteworthy projects include SyncTrainer and Auxtract, which were born out of his interests and everyday problems.

Chapter 6: Looking Ahead

With the rapid advancement of AI and technology in recent years, Raymond has noticed significant changes in the technology law space. During the initial years of his career, AI law was a niche area. However, ever since GenAI took off, clients have begun to invest heavily in obtaining legal advice prior to the launch of a new project. Furthermore, Raymond now sees clients from a whole range of sectors - banks, telecommunications, and media, to name a few. ‘It’s not just tech companies, everyone’s doing it,’ he says, demonstrating how AI has taken the world by storm.

To wrap up the interview, we asked Raymond if there are any emerging technologies outside of AI that lawyers should be paying attention to. He cites blockchain as one – ‘I imagine land registries, copyright registries, anything that’s got to do with registration can be done on blockchain,’ he shares. Besides that, he names quantum, cryptocurrency, virtual reality, and energy-climate technology as others to look out for.

As for his future plans? ‘I’m just going to keep building and see what comes up,’ he confesses.

Raymond’s projects (in the areas of law, education and entertainment) can be found on his very own website here.

 Tips for Students

  • Students who are interested in both technology and law have the option to go down either one of two paths - that of tech law or legal tech.

    During the interview, Raymond clarified that there is no such thing as tech law in Australia - it is actually a repertoire term for several areas, including privacy, IP, consumer protection, and online safety law, along with commercial contracts. This is so as Australia does not have a Technology Act. Those who enjoy being a lawyer tend to go down the tech law route, which involves providing legal advice in the aforementioned areas.

    On the other hand, those who don’t necessarily want to be a lawyer or who wish to handle ancillary legal matters tend to go into legal tech. In legal tech, the focus is on practical operations - in particular, incorporating technology to help streamline and automate traditional legal processes. Many firms currently have legal tech teams for this purpose.

  • It is not a prerequisite to have an IT degree, or even an understanding of coding and technology before getting into technology law. However, possessing prior knowledge in the field can help you stand out and will make your work a lot easier. 

    ‘For example, I remember having a matter where one of our clients was being sued by a big tech company for allegedly using their software without a license. The client had this accounting software that crunches a bunch of data and then exports it into a spreadsheet, and the big company was claiming the software as theirs. So that was a license infringement matter, and it required someone in the firm to really understand the client’s product and how it went from input all the way to that spreadsheet output. I was chosen to investigate that particular question, and that required me to look into the source code, the documentation, to really understand how the accounting software produced a spreadsheet. And it turned out that our client had not used the big company’s software; it had used another format to produce the spreadsheet. Though it sounds simple now, it wasn’t that obvious an answer. But because I sort of knew how programs work, I was able to come to that conclusion, and ended up helping our client save $42 million in license fees.’

  • ‘All the law-coding geeks, there aren’t many of us. I think all the people I know who are lead lawyers and coders are pretty much the only people of that particular type in Sydney. So the community is really small, and we’re very tight. I think it mostly started as just sharing cool things and hanging out.

    I think what changed was post-Covid and ChatGPT and all that where AI started to become a really big thing. And it’s not just a niche thing that you do for fun; it’s actually a serious area that all clients, no matter what sector they’re in, are focused on. It’s now changed the whole idea of tech law into an actual attractive space.

    And I think that’s where you still have people like me in that community who have had that sort of head start and are now just building upon that base. But you also have a new category of lawyers, what I call the laterals - so those who are very established in finance or other areas of law. They bring that valuable cross-sector experience, so they basically self-teach themselves the tech stuff, and then they marry that a lot with their existing experience to provide a very competitive capability.

    So you have a lot of them as well, and you also have the other side, which is those who have been doing general things (eg. contracts). They don’t have a particular focus area, but because of this new tech law space, they can now specialise in that.’

  • 1. Knowledge

    It is important to know who the key players are and to be aware of the key trends in the sector - so what companies are looking at and prioritising these days. With regard to Australia, be familiar with the basic privacy law framework, the basic IP framework, and so on.

    Additionally, many universities now offer subjects regarding emerging technology (and technology in general). If the opportunity arises, it would be good to take on these subjects. If not, there are many textbooks that students can look into.

    2. Skills

    There is a lot of self-learning involved in the tech law space, especially when compared with other practice areas. Tech law is unique in the sense that there isn’t one Act - it is a combination of many areas. 

    ‘Are you the person who prefers take-home assignments/exams, or long-form assignments? If you like take-home assignments, that’s what the area of tech law is like. Every day feels like a tech exam, like a two to three hour assignment you have to do. And you do three to four of them every day. If you prefer a long-form assignment where you’re given one month to do an essay, then tech law might not be for you. That would be more like dispute or corporate M&A.’

    Additionally, things are constantly changing in the tech law space. Raymond shared that his knowledge from last year is pretty much redundant this year because things have changed so much. However, while knowledge is ever-evolving in this space, the required skillset remains the same.

    3. Personality

    Students should display a genuine interest in the tech law space, and can do so by participating in a hackathon, going to a tech conference or summit (eg. South by Southwest), or reading books pertaining to the field. Given that the tech law space is ever-changing, it is crucial for one to possess genuine interest, so as to avoid burnout from all these changes.

    There is an abundance of resources available online. For one, there are many free AI courses that students can undertake - simply search up AI on YouTube, or look up the courses offered by renowned American universities like Stanford, Harvard, and MIT. As for the legal side of things, students can read articles on AI, tech, and privacy law, which are available on databases such as LexisNexis and Westlaw. 

  • The most well-known one is clerkships. Other than that, a lot of legal tech startups are hiring, and these positions can be found on SEEK or LinkedIn Jobs. Students can also go into the legal operations space of big law firms, seeking out digital and legal tech analyst roles, to name a few.

    Additionally, students who are interested in the policy side of things can consider going into tech policy. This is closer to tech law as you have to understand the underlying legal frameworks in order to develop a viewpoint from a policy perspective. Places like the Tech Council of Australia actively hire policy analysts and policy managers to advise on tech policy; and research institutions also offer policy analyst positions. Furthermore, by extension, students can also consider the role of an in-house counsel at a tech or non-tech company.

  • LexisNexis and Westlaw have embedded AI tools to help with research. Copilot, ChatGPT, Claude, and Gemini are also good, depending on what you have available. However, remember to always be careful when using these tools, and refrain from uploading sensitive information.

    ‘At the end of the day, I feel like it’s not so much what tools are out there, but finding your own style and finding your own combination of tools to do your work.’