Steve Wheeler is a lifetime technologist, catching the bug aged 7 when he got his first computer, a Sinclair ZX-81.
Today Steve is CTO of Legatics, and before his current role led various technology teams and on large scale technology projects and products at a variety of organisations, including the BBC and some of the early ISPs that later went on to be merged or acquired into the major ISPs we all use today.
If you live in the UK, there is a very good chance you use technology that Steve has worked on, whether it’s your ISP or BBC News.
As a newcomer to the legal industry and the legaltech technology niche, Steve brings a wealth of experience and insights from outside the legal bubble and is excited to share his experience and help scale and extend Legatics. Although Steve is new to legaltech, he isn’t new to start-ups, having also previously helped launch a fintech business, CrowdBnk.
Let’s dive in!
Take us back to the start. Where does your career begin?
My interest in technology began aged 7 years old. My mum worked as a Senior Systems Analyst – the first female one – at a crane company, working with the English Electric KDF9, an early British computer, and my uncle was a lecturer in computer science at Teesside University. So I always had a strong tie to IT.
It was my uncle who gave me my first computer when I was around 7. It was a little Sinclair ZX-81 computer that had to be plugged into the TV, which meant I couldn’t use it all the time!
Because I couldn’t use it all the time, it was in those early days a real treat to use it. At the time there wasn’t lots of packaged software or games. It meant copying code out of the backs of instructions manuals or magazines and poking away at that code to make it do different things, and then gradually working out what was going on and being able to build things myself. I enjoyed reading and hacking with things, so I got a lot of enjoyment out of this.
I was also lucky with school. I had some really excellent teachers who supported computers in the late eighties to mid nineties. They really let us go beyond what was in the curriculum and mess around much more freely on the computer network at school than they probably should have!
One of my first school related projects – part of my GCSEs – was trying to build a vet management system for my local vet after my sister and I got some gerbils as pets. It worked well and had quite a nice user interface that I’d had to build from scratch but it ran on a Commodore Amiga and wouldn’t really have been ready for real-world use.
As I got older, I spent time around my degree at the University of Leeds working for Electrolux, Berghaus and the Halifax bank on the side, so by the time I graduated I had a fair amount of experience dating back a long time, plus some commercial experience. I think that was helpful to stand out a bit from the crowd when looking for my first full time job.
Around graduation in 2000 I realised I wanted to learn more about the internet, which was really starting to take off – though also heading into the first dot.com bust at the time.
Against that backdrop, although I had a lot of computing experience and had used dial-up internet for a few years, I wanted to understand more about how the internet worked. As an example, at the time your modem could dial a number in Newcastle or one in Northampton or Nottingham, and you’d get the same connection – your data would go from and to the same place – which went against the way I thought it worked. So I decided I wanted to find out how that could happen.
So my first job after uni was a tech support position at an Internet Service Provider (ISP) called Planet Online, which became Energis and eventually a part of Vodafone. At the time, it was the biggest business ISP in the UK – something like one third of the UK’s internet traffic went in and out of their network.
Tech support turned out to be a great way to speak to customers directly and learn about their problems, solutions and how they were experiencing the internet and their challenges getting early websites and other web services spun up. Often this was big customers, such as Jungle.com (a sort of early UK based Amazon type business). Speaking to lots of people didn’t come naturally to me – actually I dreaded it at first – and tech support probably isn’t a role Computer Science graduates often target, but as a first career step I think it worked out well for me.
Planet Online, or Energis as it became whilst I was working there, was a really good place to learn a lot about the fundamentals of the internet. A lot has changed since then, but the fundamentals remain the same, so it’s served me well in my career as the internet became more and more pervasive and important.
From that role I moved into a team called Core Systems, that built and maintained the systems underlying third party ISPs like Freeserve, which was a virtual ISP – an ISP that resells the resources of existing ISPs, such as Energis’ resources, under another brand name. Core Systems was a strong, tight-knit team with some really great technologists – a lot of the culture and thought processes from those days are still with me now, and it taught me the importance of building systems that can be managed and maintained over time as teams and priorities change.
Whilst I was working in Core Systems, hardware wasn’t powerful enough to run a database for such a big product as Freeserve became, and inevitably my work was heavily focused on optimization so that these systems could handle ever increasing demands. This set of experiences proved useful to my later career working on highly scaled systems, such as at BBC News and their elections coverage.
In my Core Systems role I learned how to quickly build trust between the Energis and Freeserve teams, who to some extent had some healthy rivalry as ISPs, with the latter leveraging the former’s resources under its own brand.
Eventually, Freeserve – by that time part of Wanadoo – hired me. One of the first major projects I was involved in was the further re-brand from Wanadoo to Orange, which had acquired Wanadoo to be its ISP division.
Around that time I took on a new role, as a solutions architect on the broadband and mobile telecoms side of the combined business, which was great. I got to spend a lot of time on an IPTV product, a service similar to Sky’s video on demand service via a managed network, which is much less common today vs. over-the-top content (OTT), the type of internet TV service you get with iPlayer, Amazon Prime, Netflix, and so on, accessible on any device.
A busy time for takeovers! Can you tell us some more about the solutions architect role and how it differed from your prior roles?
I was a solution architect in the internal facing sense and not in the sense of facing the end users of the product. It was quite challenging at first, partly because I was and looked very young, so I had to develop confidence in myself and my role and exhibit those qualities.
I got to travel a lot in the role, especially around the UK and France. France had a more hierarchical business culture, and perhaps a little more siloed in how teams and individuals were organised functionally. That made it more challenging from a stakeholder management perspective, but not overly so. It was good to have that experience and to understand how different cultures work differently.
The main purpose of the Solution Architect role at the time was to build a path and a plan, from a business need to technology solution. In a complex business like Orange that could involve bringing together anywhere between 2 and 20 teams, each owning a part of the technical estate, and leading them to deliver the overall programme of work. As with many technical leadership roles there was a balance to be struck in terms of how far the architect should be involved in a given team’s activities and where they, as the experts, should be empowered to do what they felt was right.
Working alongside project and product managers made things a lot easier in terms of managing the various stakeholders and the creative tension between technology, product and delivery is always valuable.
Just on that point, one challenge in legaltech is that a lot of legal organisations have “legaltech” or “innovation” related roles that shoehorn about 5 – 6 different roles into one FTE, including things such as project or product management, which are individually expert and professional disciplines.
Do you think it’s preferable to have teams with specific individuals fulfilling specific functions, and ideally experienced professionals in those domains, such as project or product management vs. trying to have one person be all things to all people?
Yes, it doesn’t make sense in my opinion, and based on my experience, to cram these different roles onto one person’s shoulders. Having knowledge of other disciplines is always useful and there’s the view of the T-shaped person being an ideal – someone who knows at least a little about a lot of things but specialises in and focuses on their own discipline. But diversity in knowledge, approach and perspective is valuable and none of that is available if one person wears all the hats.
Speaking of my own experience in technology leadership roles, it never makes sense for me to do all things. To me that is not successful technology leadership.
Successful leadership – whether technology related or not – is about enabling, empowering and guiding those around you and creating an environment that supports that.
A lot of that is about communicating the parameters in which the team and the organisation makes decisions and the business drivers that sit behind those parameters.
So after your time as a solution architect you join the BBC and launch an online banking start-up, CrowdBnk on the side. That must have been pretty hectic! Can you tell us some more about those twin tracks?
CrowdBnk was a project started by a colleague and friend from Freeserve who did an MBA and decided to launch a new online business.
The idea was to provide debt or equity finance for small to medium sized businesses, largely funded by high net worth individuals. It was basically crowdfunding, but obviously different from models adopted by Indiegogo and Kickstarter aimed at funding from anyone and everyone for all sorts of projects.
It was a bit of an adventure. I didn’t really know what to expect. I didn’t get into it assuming, or requiring, it would be wildly successful – I simply got into it because I was excited to be a part of it.
My role was principally around helping design and organise the product and technology build so that it could scale and operate at an enterprise level. It was great being able to move so quickly, and to make technology decisions from virtually a clean slate.
And you were juggling Crowdbank alongside your full time role at the BBC, initially as a senior technical architect / engineering manager, and later head of software engineering for BBC News?
Yes I was full-time at the BBC and doing Crowdbank outside of work. Early on at CrowdBnk we’d also hired some full time developers, so this allowed me to dial back my direct involvement except when we had problems or were building big new features that required much more of my supervision or advice.
I was very busy at the BBC when I joined. We were having to get the elections coverage systems ready for the upcoming political elections. The system they had in place had been around from the very early 2000s and had been extended and amended numerous times, but as we approached the 2012 US Presidential election it became clear it needed a rewrite.
To do that we started building a new elections system in AWS, which was my first experience with AWS. It was also very new to the BBC, we had our team in news and one team in iPlayer sort of racing each other to see who could launch a product in AWS first.
We had a lot of challenges, but we got the election results out on the night.
The one thing with elections systems and the coverage is that if you’re late, if your delivery date slips, you may as well not bother. You can’t ring up the government officials to delay the elections or the results as they come in! You’re either ready, or you’re not.
From a societal perspective, it’s also critically important you show the right results and deliver them to people in an engaging and accessible way.
So it was a stressful, but exciting opportunity and one I really enjoyed.
Although it’s easy to think the modern up to the minute coverage is new, it is surprisingly long standing at the BBC. There’s some really interesting footage dating back to the 1979 election and before, where the BBC have the results being rung up on systems similar to a Cricket Scoring Box, using paddles to flip the vote tallies up as they come in.
How did it compare working at what became Orange, and at the BBC? Both are very large organisations but obviously quite different in their histories and purpose.
They are quite different.
The BBC is a big organisation, but it doesn’t always feel big. It’s not like I knew every one of the 25,000 or so people that worked there when I did. But different teams and product areas were relatively tight-knit. It’s also worth bearing in mind that the vast majority of the BBC’s resources go into making content rather than into technology – content is the core business and a lot of hugely passionate and knowledgeable people make it what it is. But there’s also a long and strong history of real technology innovation at the BBC, going back right to its founding. They really have driven the state of the art forward.
At Orange, there were obviously lots of different teams and there was some content production too (Ananova, anyone?) but mostly my role meant I was moving between teams on different projects, whereas at the BBC I was working on a particular product set and with that division most of the time, i.e. the News group, which included Weather and the World Service.
So the main difference between working at either organisation was my really my role, on the one hand more projects based at Orange, and on the other hand at the BBC more product and domain focused.
Do you think there’s pros and cons to being more of a specialist vs. a generalist?
I would say that in technology you can have a successful career, either as a Jack or Jane of all trades, or as a deep specialist.
I’ve ended up more the former, which wasn’t originally the plan but which I think has served me well in my later technology leadership roles. It also preserves a wider range of options, which may – depending on your personality – provide a degree of security and excitement vs. being really good and one thing, albeit some people find security and enjoyment doing just that.
If you are a deep specialist, that can make you very valuable. But if your specialism suddenly becomes no longer necessary, you can quickly be in an uncomfortable position, both with your current employer but also with the broader market of other employers. In that scenario, options might be limited absent of a reskilling exercise. I’ve seen that affect people most where the specialism is around a particular set of business tools or perhaps internal platforms, which never last forever, and it’s something I keep in mind for my own future.
There is also always a premium paid for people who can work in the cracks between different teams and specialists, as translators or bridges between these domains. So that is another reason being a little more generalist, or specialist in several areas, can be a benefit in terms of careers.
Fastforwarding to your new role, as CTO of Legatics, an online deal management platform popular with law firms and banks, what drew you to the legaltech niche? Did you know much about it as someone working in general technology beforehand?
To be honest, I didn’t know much about the legaltech niche until I started chatting to Legatics about the role.
Legaltech isn’t really any different to any other tech, but what I would say is that when I got to know the Legatics platform I thought it makes perfect sense that such a thing exists for legal professionals.
It is pretty clear to me now that for a lot of legal work there is a strong, fairly standardised workflow element, especially for junior lawyers. And so it makes sense to use technology to streamline these processes where possible.
In terms of what drew me to this sector, it’s less sector specific, but the objective challenge and opportunity it presents.
I really enjoyed the BBC and have enormous fondness and respect for the organisation. It can be a tough place to work at times but I learned a huge amount, worked with great people and had a great boss – I knew it would be a tough act to follow, and am very proud of the work my team and I accomplished there.
But when I started thinking about a new direction there seemed like two options: a large company or a start-up. I wasn’t minded to explore related industries to BBC and telecoms, partly because I didn’t want to get typecast and saw no reason why I should be.
So it was really the content and opportunity of the role, and about what I was going to learn and how I could develop myself, rather than the title or company name to work for.
And my new role at Legatics ticked those boxes.
Before Legatics, had you had much experience working with lawyers and other legal professionals?
A little. I’d been involved in various procurement activities at the BBC and Orange, a tiny bit of what I think you’d call M&A, and have dealt with lawyers in my personal life, e.g. when buying a house and so on. And of course, I got to know the Legatics founder, Anthony Seale, as part of the hiring process.
Through those discussions with Anthony, including about typical legal transactions such as financing a power station or similar – firstly it sounded horrible for the people doing these deals manually, and secondly it was very clear how technology could make a big difference to those individual’s wellbeing and their firm’s productivity.
I did think going into this space that a lot of the activities involved in legal transaction management would be undertaken by project managers, rather than someone specialist in law. So it surprised me that the repetitive assembly of documentation and other process steps were being done by lawyers. It seemed a bit mismatched from a skills and experience perspective and actually I thought it must be a disappointing bump for a new law graduate landing that first associate role.
That’s not to devalue project managers in any sense, quite the contrary – a good project manager is hugely valuable and can make a massive difference in all sorts of ways. They are arguably more skilled and effective at project management because that is what they are trained in and where their experience lies, versus lawyers who aren’t trained in proper project management methodologies and similar yet expected to muddle through using a Word table and email.
It seems odd the industry doesn’t value project managers in quite the same way most other industries do. Use of project managers would free up lawyer time to help them focus on the legal specific parts of these transactions, e.g. the negotiation, advice and specialist drafting etc – the things they are really good at, and enjoy.
What do you see as the most exciting opportunities in your new role?
I’d say getting my feet under the table and getting to know the industry is exciting.
The legal space is much less familiar to me than the world of online news, broadband and mobile systems which I interact with everyday as a consumer, and obviously spent a long time working on in prior roles. So a lot of my time is going to be spent initially learning more about the legal systems, our customers, and how the Legatics platform is being used day-to-day.
The most exciting thing is that Legatics is a great product. It’s really well-built, and backed by an organization that has a whole bunch of talented people who were lawyers, who’ve had the poor experiences we just discussed trying to manage deals and who are genuinely invested in solving these problems and making the lives of legal professionals better and helping them to deliver outstanding client value. I’ve been really impressed by the work ethic and professionalism of the entire team.
It would be great to make Legatics the landing page for all legal business within transactional teams. I can see a path to that outcome.
I’m going to be spending time helping us scale the platform, and adding more developers to the team to help with that objective, especially as we increasingly widen the customer base.
We have some experimental AI capabilities we are weaving into the platform. We’re not an AI organisation, and deliberately avoid that label. For us we are trying to find subtle but powerful means to apply targeted AI capabilities where it can make a big difference to the workflow and productivity of users in the platform. I’ve not worked with AI technologies before in any great depth, so this is particularly exciting for me to get into and help build out as it’s something I’ve been keen to explore for some time.
What career advice would you give to people, including anything you know now that you wish you knew earlier in your career?
I’d say look for roles or opportunities to take on meaningful or complicated problems and the time to make them good, and make them happen. Show that you can get things done. Opportunities aren’t handed out, but taken. You’ve got to find them and then take them.
You need to be humble, and not be averse to doing the monkey work where necessary, especially at the start of your career or a new role. But equally, don’t feel that sort of thing is beneath you, whatever level you are at.
Variety has served me very well, but might not suit everyone. I think it’s good to get involved in a lot of different things.
When I was growing up I was a bit of a shy geek, bullied a bit at school, so I wasn’t particularly outgoing or talkative. So working with the great teams at Energis and Freeserve and interacting with a lot of people in those roles made a big difference and gave me confidence and a lot of the skills that were valuable later into my career. It’s definitely worth consciously getting outside your comfort zone.
As a technologist coming into the legal industry from outside, do you think lawyers should learn to code?
I would never tell someone not to code, but I’d suggest they be sure why they’re doing it, or want to do it.
You know, is it that you think you can do better than the coders in your organization? Are you going to be straying into their lane, standing over their shoulders or telling the boss they’re doing it wrong? Is that going to be a productive thing to do in that sense? Where do you want these skills to lead?
If you are going to code, are you going to spend enough time learning to code that you’re good enough and experienced enough that you’re helping, rather than hindering processes that involve development?
Product is again an exciting discipline and there’s some great career paths around product. Maybe as a former lawyer with some technical and product skills under your belt, you can become a great product manager for legaltech applications – and then beyond, if that’s where you want to go. But you really need to commit to learning how to be a product manager, simply being a lawyer that has done some coding isn’t likely to be enough, though it’s a start.
Even if you take some time out and do a 6 month full-time coding bootcamp or similar, you will need to expect that you’re competing against a lot of individuals with significantly more experience, so you will need to consider taking an entry level developer role initially if you want to go down a purely technical route. That said, you may well be able to progress quickly as your technical knowledge grows, because of your prior experience and skill.
I think that’s worth stressing, simply to manage expectations.
As I say, things like software development and product are high-skilled disciplines with a huge body of knowledge and continuous evolution, much the same way as law is – you can’t simply swap hats and expect to land into a senior and influential role straight away. That shouldn’t discourage anyone wishing to tread that path, but more something to be cognisant of before making a big decision.
I’d agree. A lot of developers, like you, have been coding since they were quite young. Not always, but quite often that is the case. They also have a real passion for it. If you are a lawyer and complete a few hours of a coding course, let alone a 6 month coding bootcamp, you will still be much more junior in experience than the average career developer. Being self-aware of that is a must if you’re career changing from say law to development.
Lastly, do you have any books, podcasts or other media you’d recommend regarding technology, start-ups or careers?
I like podcasts a lot, but I tend to listen to international relations and politics. There’s a group called Deep State Radio, which gets some great policy experts and is worth a listen if you’re into that domain.
I’m also a big fan of Reddit, HackerNews and Lobsters. HackerNews can be a bit of an odd community, but it does have a lot of interesting content. Reddit can be a bit unwieldy, but there’s a ton of interesting information and discussion on there amongst the noise.
Newsletters are another channel I enjoy. For a while it was written off as a media category, but seems to be making a comeback. Some newsletters I’d recommend would be:
- The Silicon Valley Product Group founded by Marty Cagan is a great product management resource, and he also has a product book out at the moment, Inspired: How to Create Tech Products Customers Love.
- TLDR Newsletter is a great daily newsletter with links and TLDRs (summaries) of the most interesting stories in tech, science and coding.
- Pycoders is a great weekly newsletter for anyone interested in Python development and various topics related to Python.
- CTO Craft and StaffEng are great resources for engineering leaders – not just for CTOs. CTO Craft has a really strong community, especially in the UK, and recently held its second conference
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