I’ve always enjoyed reading career stories. I’ve always found it interesting to read the journey people have taken – especially in legal tech/ops. I can’t imagine anyone as a child saying “Mummy, when I’m older I want to be a legal technologist” yet for many this is a role and career that exudes a lot of passion.
Passionate people hungry to change, transform and improve ways of working in the legal space – pitching themselves against traditional ways of thinking and doing things. It’s a journey that takes them on (and through) trials on a quest for continuous improvement – advising or implementing their way to a better legal team or law firm one project at a time.
I started The Legal Technologist nearly eight years ago and have always been grateful for those that have shared their career stories over the years. Sharing career stories promotes what is possible. That you don’t always have to follow the mainstream or traditional routes. That you don’t just have to be either a Solicitor or Barrister if you’ve done a law degree.
I hope that over the years people have been inspired by reading others’ stories – and through that they’ve been able to find a role in legal tech/ops that they make their own. Perhaps even allow conversations to start and connections to be made. I hope that over the years the people that have shared these stories have described what it means to be a legal technologist.
“Sharing career stories promotes what is possible”
I’ve shared my story briefly in the past but I thought it would be useful to also share my own too. So here goes..
Early Years
It’s fair to say I could have done better at school although family circumstances hadn’t been ideal at the time. Although I passed my maths GCSE a year early I think I lost a lot of focus by the end of my last year – ultimately leaving secondary school with a handful of GCSEs.
Leaving school I felt like I didn’t want to pursue the same path everyone else was taking. Many of the others I went to school with went to one of the colleges in Cambridge. I did a Public Services course in Hitchin instead. I had visions of becoming a Royal Marine and this was (I think) the middle ground that kept me in education. I dropped out of the course in the end and I distinctly remember being told that the military wasn’t for me by one of the tutors.
The following year I tried to rejoin the traditional path and did AS levels – I got to the end of the year but felt like full time education was no longer for me. I’d done best at law (and I really enjoyed it) but knew that it would be a long path to university with the other grades I had.
At around this time my cousin was joining the Army and I followed suit not long afterwards. He joined a tank regiment and I joined the Royal Corps of Signals to become an electronics engineer.
Personal Transformation
People have different views on the Army but for me it was transformational.
It took around a year to get fully trained – from basic infantry skills to how to repair digital radio systems in the field. My electronics course dwindled from around 20 to 6 over the time I was on it as people failed exams and had to be re-traded. The perk of the role was that you’d get promoted as soon as you’d finished the course. I was still a bit immature when I finished and of the six of us – only I didn’t get promoted.
It was crushing at the time. I knew that it would be really obvious that I hadn’t been promoted as soon as I got to my new unit in Germany. In hindsight though, it was almost certainly the right decision. When I got to my new camp in a small town between Dortmund and Hannover I wasn’t really sure what to expect. I had a manager there that steered me in the right direction though.
I remember him giving me a year planner and telling me x number of days were blocked out for exercises. For the remainder of the year I should get on as much as I could – courses, adventure training, operational tours, etc. It was about six months before I got promoted (at the next promotion board) but that time shaped my mindset. I wasn’t going to be handed anything – if I wanted it I had to grab it with both hands.
“I wasn’t going to be handed anything – if I wanted it I had to grab it with both hands”
Making my way into law
I spent around four years in the Army – spending much of that time abroad either in Germany where I was based on operations in Iraq. I also spent time in Poland on exercise, mountaineering in Bulgaria, yachting up Denmark, as well as visits to Qatar, Kuwait and Cyprus.
Going on operations gave me a sense of perspective. That life wasn’t as long as I’d anticipated. Seeing people write goodbye letters to loved ones just in case the worst was to happen was a wake up call. I felt I still had plenty more to accomplish in life. Over this period I found I could do distance learning courses with the Open University (OU) so I pursued their law degree.
The OU’s law degree is done in six parts – each nine months long. I got through the first one and really enjoyed it. That spurred me to look at leaving the Army and going to university full time. I remember putting in my UCAS application while lying on the floor as another rocket attack hit Basra camp. There were a few close calls but I was ultimately lucky to return ok.
“I remember putting in my UCAS application while lying on the floor as another rocket attack hit Basra camp”
From law to lawyer
I left the Army and went to the University of the West of England in Bristol to do my LLB. Around this time the recession of 2008 was starting to bite and by the time I left it seemed like law jobs were scarce. In the end I went travelling for 10 months across SE Asia and Australia with money I’d saved up working during my degree.
I returned to the UK getting a Knowledge Services role at Clarke Willmott – sending out journal articles to fee earners and working with PSLs on automated real estate documents. My first taste of automation in legal. I think the following year I flew to Singapore to be with my now wife and stay with her and her family there. I was sat by someone on the plane who offered me a role at a Shiitake mushroom farm – getting a role before I even landed there! This role and another allowed me to stay in Singapore for about seven months – before I made my way back to the UK to do the Legal Practice Course.
After finishing that I managed to get a temporary paralegal role at Simmons & Simmons looking for insider traders in their team focused on white collar crime (which actually lasted around six months), before moving to RPC as a claims handler (later becoming a paralegal). It was enlightening on both counts – but particularly the latter as it related to professional negligence (claims made by clients against their lawyers).
At RPC a carrot was dangled to the paralegals that they could qualify as a solicitor through a route called Equivalent Means – but that we would need to find out more about it (as there was very little info). I liked the thought of this – partially because it felt like I had the power to do it myself (rather than be subject to selection by others) and also I didn’t like the thought of having to wait two years for any training contract to even start.
I found a few others that had completed it, got the info I needed and did everything required to get qualified (see article here in The Lawyer). I was also pleased to help three others through the route not long after me too. It had taken about seven years to get my practising certificate so it was a relief to finally get there! (big thanks to Austin, Sanjeev, Rob and Ian who were all supportive at RPC during the application)
“I read all the release notes for the solution I was using and tried to squeeze out (and pitch) as much functionality as I could”
The road less travelled
At this point I had a choice – pursue an Associate role doing professional negligence or take the road less travelled and become an Automation Specialist. I knew I wasn’t so passionate about prof neg work (sorry prof neg lawyers!) and I enjoyed the technical side of things – so ended up taking the latter. My remit was to roll out document automation across the firm and I learnt a lot about automation, change management and return on investment.
I read all the release notes for the solution I was using and tried to squeeze out (and pitch) as much functionality as I could. After a few years I then moved onto SYKE (now fully absorbed into Consilio) automating documents and helping with client RFPs. This progressed to CLM where I eventually led a team of 25 – 30 people implementing Icertis.
There was some pretty insane growth over that period. In the end it burnt me out, and with my second son imminent, I knew working late every night wasn’t going to be sustainable. I moved to a new role internally and spent some time helping with DocuSign CLM projects and projects in need of a lift. After about six months I found myself at another crossroads.
A new door opens
Around this time I was looking to grow The Legal Technologist and bring in some advertising revenue to fuel that growth. One of those conversations led me out of consultancy and towards marketing – arriving in a new role as Contract Mill transitioned to Ment. It was great to spend time with Kaisa Kromhof seeing firsthand what founder life was like. I think I’d only been in the role for about nine months when M-Files acquired Ment and with it I’d moved to another role again. This time into the industry solutions team which focused on solutions specific to particular industries – which fell under the remit of the marketing team.
I learnt a lot over those couple of years – both in relation to the job itself and also Finnish culture. I’m a big fan of travelling and it was always great to make my way to Helsinki or Tampere. It was a shame that in the end the company had a large restructure and I fell victim to that.
It was a bit of a long goodbye and while I was going through the motions to leave the company I decided I would post up on LinkedIn to see if there were any opportunities out there. Thankfully I had a few people get in contact – ultimately leading me to my current growth role at Document Drafter.
No time like the present
So that’s the story so far.
I’m currently Head of Mid-Market Growth at Document Drafter – enjoying speaking with people from around the world looking to improve their legal drafting. I’m also Founder of The Legal Technologist and Co-Founder of Legal Tech in the South West – bringing together people to discuss the latest topics in legal tech/ops/design.
My path so far hasn’t been straightforward. Perhaps I could have made things easier for myself, but maybe that wouldn’t have made me as adaptable and resilient as I am today. I wouldn’t change any of it though as I’ve learnt so much over the years – and continue to do so daily.
I guess I consider myself a late bloomer travelling the path less travelled – not specifically beholden to any traditional path but making new tracks when required. When I ask people to offer their career stories I usually ask at the end what advice they’d give to others pursuing the same role. My career is a bit ‘squiggly’ so perhaps I’d round off with some things that have worked for me over the years:
- You don’t ask, you don’t get – In essence, this is really a phrase about boldness and perhaps curiosity. Asking the right questions opens doors, creates opportunities, progresses careers and allows you to learn. Don’t waste time deliberating over whether to ask things.
- Make the most of everything – I did this in the Army originally but then when I got to RPC I remember doing all sorts of things – using up available budgets to organise charity and festive events (I even attempted to organise an office ‘jailbreak’ event but didn’t get the approval!).
- Improvise, adapt and overcome – Something I undoubtedly picked up from the Army but in essence it’s a mindset where no obstacle is impossible to get over. An obstacle is simply a puzzle – if you can’t crack it the first time, keep on trying different ways until you do.
- Don’t do something you don’t enjoy – I think this where the passion comes in. Doing something you’re passionate about makes a difference to you and the people you work with. It could be that additional effort to roll out a bit of legal tech or spending additional time learning about a tool to get the absolute most out of it. Ask yourself whether you want to be the best at what you do? Do you have the passion for it? If not, perhaps it’s time to move on.
- Never stop learning – become a lifelong learner and learn as much as you can. Keep up to date on release notes and learn new functionality. Horizon scan your niche and understand the differences between what you use and what is available. Maintain your skills and upskill yourself to remain adaptable and flexible to new roles and opportunities.
If you’ve got this far I hope you enjoyed the read. Feel free to connect with me here.
My adventure continues – I hope to see you all along the way.
