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.
Go With The Data Flow – How Raymond Sun Turned His Passion Into A Career
Author: Ashleigh Cheuk
Interviewers: Jessica Woodyatt, Tiffany Lu & Ashleigh Cheuk
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.