In this episode of LawTech Industry Insiders, Nathan Corr is joined by Samuel Smolkin, founder and CEO of Office & Dragons. Sam is the Founder and CEO of a leading platform in Transaction Development – Office & Dragons. Before founding O&D, Sam worked in private equity as an M&A lawyer at Kirkland & Ellis.

Q. Please introduce yourself and your career journey to date

I’m Sam, the founder and CEO of Office and Dragons. Before I made the crazy plunge to be an early stage start-up founder I was an M&A lawyer at Kirkland and Ellis working on big international private equity deals for private equity sponsors.

Going back a little bit before that you can probably tell by my accent, I'm American. Over in America we do an undergraduate degree before a specialised law degree and in my undergraduate degree, which was also quite a journey, I started out in engineering and that's where I first learned programming and I kept that up as well throughout the years. While I was working at Kirkland & Ellis I was working on some open source software on the side and as I was doing those two things I think it help me bring sort of a different mindset to my practise that maybe was a little more ‘engineer like’, and so looking at a lot of the activities that I would have to do on a more mechanical level like I need to draft these documents; I need to align on this piece of information; I need to have this call do this and that really breaking it down; and thinking about you know “why is this so painful?” and especially why are some of the things that I do particularly in the legal world as a lawyer so painful when similar things that I might do in the engineering world as a software developer were relatively simple straight forward fast?

So that's what got my gears turning I started working on a prototype of what I thought would be something that could help take away a lot of that toil from my own work and just help deals get done faster better or more accurately. I started talking to a few folks about it and realising that this idea could be wider than just helping me in my own work that it could actually have some wider spread applicability to the work my firm and my clients and others were doing and that's it really kicked the ball rolling with Office & Dragons. Eventually we got accepted to the Barclays Eagle Lab incubator where we raised our first funding round. Since then, we have been building the team doing pilots of the product and yeah it's been it's been quite a wild ride - especially these past few months.

Q. What does your role as the CEO of Office and Dragons involve?

When I first started the company, it was everything because I was the only one – but now it's a little bit of everything. Day to day, I spend a good amount of time interacting with our customers and prospects, I do that a lot with Logan who is our Head of Business Development. I also spend a good amount of time working on the product not so much coding although I did more coding in the early days but now more from a product design perspective working closely with Wilson - who heads us up on engineering and is the one doing most of the coding now along with other engineers helping him.

I also work a fair bit on the content that we produce with Cherry who is our lead on design. I work with yourself Nathan and with Ketsy on a lot of core sort of identity and branding materials that are ways in which we show the world who we are and what we're doing. I also work with Matt on various operational matters. Besides for that, a few things which are purely my lane - like communicating with investors looking for more investment and all the other good stuff that founders tend to do and everything else that no one else is doing.

Q. What does Office & Dragons do and what does it view as its market?

This is actually something we've been spending a lot of time sitting down and formalising over the past month at the company. Taking a step back, a core insight stemming from what I was talking about before about being a lawyer and an engineer is that the job to be done of a lawyer, when you abstract away from it, is to take a complex system, and that system is the deal that's happening between parties, and to reduce it to writing contracts documents and things like that to actually affect the deal and make it happen the way the parties, particularly your client, wants it to happen.

Of course, I'm talking about transactional lawyers and when you look at that problem generally that's a problem that's already been solved to a large degree in another field and that field is software engineering. There, software engineers are likewise able to take a complex system, which is the software they're trying to build, and they reduce it to writing to which is the source code. But as I was saying, I noticed that in software engineering they have paradigms principles and tools that let them do that for relatively much more complex systems relatively quickly, accurately and simply.

Our core insight is to bring that to the legal profession and that's why we call our category “Transaction Development”, because transactions, unlike the documents that lawyers write today, are not just something static that you can just capture right away. Transactions develop over time between the parties and likewise the transaction documentation needs to develop and keep up. First drafts, negotiated copies, agreed forms, final forms - a lot of the friction and pain that I felt and my colleagues and my clients felt as well working on transactions was keeping up with all that change. Keeping up with the flow of information making sure it's reflected where it needs to be. That the deal documentation reflects the deals that all parties have a shared understanding of - those deal terms as the transaction develops and evolves. So that's what we're trying to do we're building a platform that helps lawyers and clients come together and align on deal terms. We are building simple models and using those simple models to automatically create and edit documents eliminating a lot of that friction back and forth, driving greater accuracy alignment. Once that data has been modelled, it can be used for other things too. Beyond just that one set of documents you need to create after the transaction people need to look back and refer back to that information. Maybe there's going to be a follow-on M&A deal, or something of that nature. With that information which needs to be resurfaced, rather than having to dig it up again through the documents and maybe even get it wrong as it's been a while and maybe the folks who did the deal are no longer there by having it already in a structured form it makes the data reusable down the line as well.

What benefits does transaction development offer to law firms and their clients when editing documents and working on transactions?

To back up a little bit and kind of frame the problem we're looking at in a nutshell. The way that transactions are getting done today is changing. They're getting faster they're getting more competitive and legal cannot be allowed to remain an expensive bottle next to that process. Legal needs to keep up and when we look at what's the problem, what is keeping legal from performing at pace with a lot of what's been going on, say in finance with the rise of fintech, it's that the way that lawyers and clients work today it's a lot like an author and an editor work on a novel. They draft these big static tax documents and they trade mark-ups back and forth. It's a craft, so to speak, which makes sense because lawyers are educated - sort of like craftspeople, they're taught to look at things individually. They read and analyse individual cases, work on individual documents and you know that it's a lot like the people who first made automobile. They are the craftspeople who had to know about every nut and bolt and how it fits into the car and make the whole things themselves. They sure could produce some really nice automobiles, but that process wasn't capable of putting a car in every home. It was the introduction of the assembly line and manufacturing engineers that could do that. The big difference is that they were no longer looking at a person who knew how to build one car at a time, they were people who knew how to build cars in general. So legal needs that as well. We need to train our lawyers and clients to not just think about individual documents and individual pieces - but rather to work on the transaction as a whole. How do you do that? Well, the biggest thing is you need to be able to work on any big problem is you need to be able to separate it out into pieces and that is just as true in law as it is in software development. In software development, one of the biggest paradigms is the separation or decoupling between different pieces of the system and one of those big things that they de-couple is the data from what's known in software as the ‘views’ - which is anything that relies on the data.

So data could be some numbers, “123”, and the ‘view’ might be a web page and a mobile app and something else that shows you those 123. But the key thing is when you change 123 in your model of the data it should change everywhere in your web app and on your mobile phone as well. That's what we want to bring to legal. Rather than working on individual documents one at a time like static manuscripts, lawyers and clients can instead align on the key terms for their transactions and in a really simple way, lay them out there outside of all the documents so that they are really easy to find and really easy to understand. Then they can use those models to automatically create and edit those documents. What that does is it removes a lot of the friction from alignment on key terms between lawyers and clients and internally within law firms - let's say between various members of the legal team. It also greatly simplifies the review process because with all the information in one place we're no longer hunting across hundreds of pages to find it and we can change it quickly when we need it. By using that to automatically create and edit documents, we're taking a lot of the time and friction out of that drafting process and a lot of the room for error so you know – “measure twice cut once”. Set everything up in a simple, really easy to look at, review and understand kind of way and then let it create and edit documents fast.

Do you think having a background as lawyer helps when pitching Office & Dragons to law firms?

I think it depends on who you're talking to in particular. It certainly can be useful in a few ways. I mean one way is that whenever you're building or selling anything it's always important to know your user, your customer, who you're making it for. Getting into their head helps you build the right thing. We do that through building personas and conducting interviews and things of that nature. So, coming in with a background in that field certainly helps because you're not starting from zero. But I would also say that there's also a big risk when you're coming from that background. The risk is that you assume that because you lived it, you know it. The fallacy you're making there is your extrapolating your own personal experience to everyone. You're assuming that everyone thought and felt and work just like you and it can be really dangerous because that means some founders/product developers who are developing for their own industry, whether its lawyers moving to legal tech or bankers moving to fintech, they may skip that step where they do the interviews and the personas and all that and just build something essentially for themselves. They might get lucky in that their experience just happened to be really representative, but odds are it wasn't and they can run into a lot of trouble if they've gone a long way building a product that's not actually fit for the users as a whole. So, it’s a double-edged sword.

Why Office & Dragons as a name for the company?

Well, I'm a nerd and like nerdy things, so it's a Dungeons & Dragons reference. But back when I was first fantasising of some software to help me out of my work, as you're doing a typical late night at the office and I thought to myself I sure want something magical to save me like a wizard or a dragon, and the office felt like my dungeon at that time. I think that's when I put two and two together and we got “Office & Dragons” as a name. Since then it's kind of stuck. One of the other things which is why we stick with it, and why to a larger point why we have the branding we do and why we're not called “Legal X” or something like that, “Legalise” or these other kinds of names. Why we don't brand to look like a law firm or something high-tech and like a robot factory or something, is because you're your average legal professional isn't necessarily right out there thinking about all the coolest techs and Ais and all that other stuff. I mean they're thinking about getting their job done. Especially in a profession that's based on using the experience from the last time to do the same thing with a twist this time and take only very measured risks and things like that. C hanging the process in any way can seem really scary, especially when you have big words like “automation” and “artificial intelligence” and stuff thrown out at you.

What we want to convey is that it's not scary. This is meant to be something that ultimately makes your working life more pleasant, more productive and ultimately lets you have a little more fun with your job and with life when you're not stuck in the weeds and your doing more of what you want to be doing. Whether it's tackling those big intellectual legal problems or whether it's honestly just spending more time with family and friends. So that's what we want to convey. That's ultimately our vision and the benefit we want to bring to our users.

Should students be taught about technology as part of their legal education?

I actually wrote a piece for the Legal Technologist the other month where I had the time to think about this a bit and what I came down to was similar to the conversation before about craftspeople versus engineers, cars versus production lines. I think that law students should be taught to deliver legal solutions. A legal solution is hard to define and I don't think I have a great answer of what exactly are legal solutions and what does it mean to deliver them, but at the heart of it is solving somebody else's challenge or their need. Whether it's in a commercial context, the needs of the client who's trying to do a transaction. Whether it's in a litigation context and to defend and uphold the lawful rights of the client of the attorney, in that case we should be taught to think about how to how to deliver those outcomes using the law, whether it's the law of contracts or the practise of law. Not even necessarily the law of contracts, but the process of contracting and entering into contracts or the process of arguing a case based on precedent and things like that.

So taught to think more about the process and I think technology of course has a part to play in that process because I mean software is eating the world. There’s nothing but technology I mean that's the way we're going. Technology is part of everything so I would say that lawyers should be taught to deliver solutions and technology I think would inevitably be a part of that. I don't think it would be helpful just to have a class like “learn coding 101” for lawyers or something except just to get like ideas rolling I think it's more about engineering and designing solutions in a legal context and how technology would fit in there.

What would your advice be to students who want to learn more about technology?

Personally I learn a lot by reading a lot and by doing. So I look for any sort of resource out there that both has some sort of ‘how to’ tutorial and then some sort of exercise where you get to challenge yourself and try to make something especially if it's something useful to yourself. So I think the best way to learn about technology would be to start with a goal. What is it that you want to do with technology? I mean do you want to write programmes because you think that could be cool or do you want to design products because you think that could be cool or do you want to help connect people who need technology with technology that's out there? There's all these different things you could learn about technology and what you could do there but if you start with understanding your goal then I would say go online and look for any resource that's out there on the topic read some “how tos” that are related. Maybe take some video courses and then try to do some sort of project related to that. So if you want to code some sort of chat bot for legal advice and it’s your dream to build it then maybe learn about building chat bots and then as a project try to build your own a really simple one. It doesn't have to be fancy but maybe it will just say “hello” or something else and that's where you can start. Also always reach out to people too. I think one of the really beneficial things about COVID, I mean they're not many obviously it's been bad as a whole. But one of the beneficial things is that people seem to be really open now, relative to before, to connecting digitally and just have more time for it. I have one or two calls with the students every week and these are students who just reach out to me through LinkedIn or some other social media and I find myself pretty willing to make a half an hour to sit down and chat and try to share what I've learned so that I can be helpful to others - so do reach out to people.

About Office & Dragons

Office & Dragons transforms documents from static text into dynamic representations of data, making document-making simple, reliable and fast. Their app has a simple, familiar "find & replace" style interface that legal professionals have mastered in just 30 mins of training, and it works with any documents, not just templates prepared in advance. They are based in London but have employees in three different continents.

For Students

Office & Dragons is always looking for new talent and welcomes student interns. To enquire about new opportunities, fill out the ‘Join Our Team’ form on their website at: https://www.officeanddragons.com/.