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Career Legal Tech Associate

The Legal Tech Associate – Jack Shepherd (Freshfields)


I am not one of those people who has wanted to be in law from the day I was born. Unlike my barrister brother, I never received birthday cards with the letters “QC” appended after my name. I did, however, have an interest in technology from a very early age. I developed my first website when I was 12, and started my own website design agency a few years later. 

I knew I wanted to go to university, and computer science was the natural choice for me. However, after researching the course I realised it was more of a mathematics course than a website development course. I didn’t think it was the right choice for me after all.

With a-levels in an eclectic bunch of subjects, I eventually settled on studying law at university. It was not really because I was passionate about law; more because there was nothing else I wanted to study or could study. Similarly, I did not especially want to have a career in law.

I was considering my career options in my second year and got on really well with some people I had met from Freshfields. I attended some open days and felt that it was a place I could work and flourish. After a vacation scheme, I secured a training contract. 

On day one of my training contract, I remember collaborating with my supervisor on an advice memo. Our method of collaboration was one familiar to most lawyers. It worked by  me producing a first draft, printing that first draft, and for my supervisor to mark it up with a  red pen. I would then type those changes into the document. This cycle repeated itself a number of times for each draft, before it was submitted to the partner. The partner changed nearly all of the document. So from day one, I had an interest in how legal processes could be optimised.

I qualified into the restructuring and insolvency team after my training contract. The people in that team are some of the most talented people I have (and probably will) ever work with. They are extremely dedicated to the work – but perhaps more importantly, are thoroughly pleasant people.

Nonetheless, as interested as I was in complex restructurings, I always knew it was not my life’s mission. I still had a very strong interest in technology, and my restructuring role was not making the most of this (except for sharing wisdom when it came to tips in PowerPoint and Word).

The opportunity to act as a product manager at Freshfields arose a few years after I qualified. I jumped at the opportunity. 

Taking this role was the steepest learning curve of my life. It was made even steeper by the fact that I had a technology background. While I was able to understand technical concepts well, this was a distraction to where I could add the most value to the team in my role. 

Instead of focusing on business outcomes, user experience and strategy, I was more interested in diving into technical matters. I was also very skeptical of anybody who tried to tell me that I would have more success following design sprint methodologies involving whiteboards and post-it notes. For me, these were time wasting distractions from an important delivery objective. 

Thankfully, I performed a complete u-turn from this position. I am now usually the first person in the room to try to take the conversation away from technical matters and divert them to business outcomes of a given initiative. I have an obsession for process mapping, identifying personas and spotting problems before jumping to solutions.

My work at Freshfields has taken me from law to product development right through to how to instil change within a large organisation. It has helped me realise that most lawyers are not really interested in using new technology. They are interested in how their working lives could be improved – whether that be by increasing profits, reducing wasted time or improving culture. Technology is only relevant insofar as it achieves these goals. Often, people prefer it if you can achieve these goals without technology at all.

I am extremely fortunate to be forging a career path that combines technology with my passion for driving change in law. I will shortly move from law firm to technology company, when I start in a new role with iManage RAVN at the end of the year.

Jack Shepherd
Legal Tech Associate at Freshfields


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