00:00 From Law to Legal Tech: A Journey of Discovery
03:36 The Impact of AI on Legal Tech
08:44 Navigating Customer Expectations in Legal Tech
13:55 The Challenges of Non-Technical Founders
18:16 Building a Responsive Tech Team
21:58 Embracing Entrepreneurial Journeys
21:58 Investing in Women: A Better Return
27:55 The Importance of Design in Tech Solutions
31:03 Future Aspirations for Deeligence
33:09 Learning from Mistakes: Stumbles of the Week

Elena Tsalanadis (00:00)
Good ideas come from everywhere. We wanna build this intentionally psychological safe environment because we know that that's what the best performing teams are comprised of where the best idea wins every time. It doesn't matter if it comes from the most junior team

So we really wanna uplift those voices.

Megha Sevekari

I would love to start off with you telling us a bit about yourself, but also you started your career in private practice. I'm really keen to hear about what you liked about it, but what ultimately made you still leave it to join Diligence. Sure, so my background is as a lawyer. I worked in litigation, court appearances. I was a bit of a nerd and I always knew that I wanted to be a lawyer and go to law school.

Elena Tsalanadis

I think when I landed at a law firm, even though it was a wonderful firm, I felt like it just wasn't the right fit for me. ⁓ I felt like there was just this entrepreneurial side of my personality and spirit that really isn't being utilized as a junior at a law firm. So I ⁓ briefly worked as a judges associate for a Supreme Court judge, which was a wonderful work experience. And I moved to London.

And in London, I tried to pivot out of being a lawyer and private practice into working at a legal tech startup. So I helped another founder build and scale a tech solution and deliver that to lawyers. And when I returned home, I thought, okay, I've done this for someone else. I think that there are other really juicy problems to solve for lawyers because so much of their work is repetitive and manual. It's time to do it for myself.

And that's how we began Diligence, trying to first figure out what's a thorny problem that lawyers experience as subject matter experts and then build a really beautiful solution to solve that pain. Was there anything when you were working at that startup and building the legal tech? ⁓

Megha Sevekari

that made you really say this is what I wanna do?

Elena Tsalanadis

I think I've always been one of those people that wanted to run their own business. I think there's gonna be folks out there that that really lands with like, yes, that's me. I've always wanted to run my own thing, grow a team, solve a problem. And so I think I have always been that way inclined. Working in a startup is just the absolute best way.

working for someone else, I should say, in a startup is just the best way to touch all the aspects of the business, get your hands dirty, learn how to solve a problem that's not your problem but for someone else. So I think I had always been that way inclined, having then experienced working in a legal tech, I could just see there was so much space for disruption in the field and that I really had something to add meaningfully to that discussion.

Megha Sevekari

And just on that, you also said that you get to dip your hands into a lot of different types of areas in the startup. Before that, did you have any tech background? And if not, was working in that environment helpful to kind of get accustomed to this new space? Yeah, so I'm a non-technical founder. ⁓

Elena Tsalanadis

I think that brings some strengths and some limitations. When I was at that UK-based Legal Tech, I was in a purely operations role. So as a classic type A person, I love bringing systems and processes and improving the way people do things. And I think that that's something that I've always done throughout my career, even pre-startup life. I've always prided myself on figuring out really clever ways of improving

the way people work. So I guess working in cross-functional teams at a startup is an amazing way to work with people who have different areas of expertise.

So I wore my operations hat. I worked with ⁓ sales team members, technical team members, and founder, co-founder to help understand a problem and kind of build and grow a solution. So now that it's my own company, I think maybe part of the naivety of a lot of founders is...

you kind of say yourself, how hard could it be to learn this thing? Answer, it's really hard, but if you have an appetite to learn and a thirst to kind of just figure it out, I think it's like a get shit done quality about you, which I think I definitely have in spades. You then just start acquiring skills, and if you don't have them, then you go to the right people who do. And so a big lesson for me is,

Sure, there are some things that common sense and books and podcasts and talking to friends in your network will help you move up the scale of learning. And there are some things which, like you don't have the skill set and you may cobble together a solution, but really you need to go to the experts. So that's when we leverage like amazing folks who we work with like at the folks and until now, because I think like I have a good eye, but I'm not.

someone that you want to be trusting to design a beautiful legal tech product, right? Like you've got to sometimes go to the experts.

Fra (06:11)
I'm curious to ask you, what do you think is changing in legal tech? Because law has always been one of these categoriesit moved a bit slow from a tech perspective. And then

Fra (06:26)
In the last two years, mean, I know AI came in, but like, what's the change in terms of mentality? The industry feels like it's much more open than it used to be. Yeah, what's your take on it?

Elena Tsalanadis (06:41)
So my take is I think there has been a seismic shift with artificial intelligence. If you are a person moving through the world, you are probably using, experimenting, trying AI in your day-to-day life.

that might be to find a recipe or to figure out a shopping list, say. So I think that there is just this collective push and drive around the importance of artificial intelligence in everyone's lives. And that has really changed how people are looking at professional services and how the way work is being delivered in many industries. So not just legal.

What's really exciting is lawyers sometimes have a reputation for being risk averse and not wanting to change their processes. That's not every lawyer. think the great lawyers ask themselves, could we do this a better way? So I think there's always been scope for folks to engage with technology to help them deliver their work in a more efficient manner.

But now what I'm hearing from conversations that I have with partners at law firms and really senior folks who procure technology at the biggest and best firms is that people are saying, like, do we have AI for this? Like, what can we do to make sure that we're competitive in this changing global landscape? And so it's so interesting as a vendor, and now as a vendor that is an AI company to engage in those conversations, I think sometimes they can lean towards a bit of overhype.

You know, I think that the most sensible and the best way to approach a problem in your business, whether it's a law firm or otherwise, is to look at the problem you're trying to solve first and...

understand that problem really deeply before you think about what sort of solution fits. So that may be AI. It might just be a killer product that is, you know, low code automation. But I do think things have really drastically changed in this industry. It's incredibly exciting. Do you find that because they want AI, there are too many expectations sometimes?

Such an interesting point around too many expectations. I was just at a conference and I was chatting to a whole host of folks and we were talking about how as lawyers we're all perfectionists and I suffer from this myself, right? Like we're all iPhone native users where everything works or you use Google Drive and Gmail and there is no bugs that you encounter, your experience is seamless. So I think partly we just expect stuff to work and have no problem.

and then if you add that additional layer of, in our case, our customers are busy corporate lawyers running deals, they are time poor. Like our platform has to be nearly perfect to fit into the way they work or they'll never use it again. And so it's a really, really high bar because we want to put something in their hands that works even though we're a company that is still growing and adding more features. So it's a real line that we have to walk between.

being robust enough and also new.

Megha Sevekari

Do you think that also impacts the types of people you, or the types of lawyers you approach who might be a bit open-minded to recognizing that it's not gonna be as seamless as Google, which has existed pretty much forever at this point. So do you kind of change who you approach, how you approach with that in mind?

Elena Tsalanadis

Yeah, so I think probably we've done not a good job of that. So it's really hard. You're selling a dream about what your product does and the time it saves and how amazing it is. But it is crazy to think that there would not be any questions, some confusion using a new tool, a bit of a ramp up, or maybe something just does

or behaves in an unexpected way. So I think we're getting better at saying, know, if you have a question or a comment or something's not working the way you envisaged, let us know and we can help guide you through that. Or perhaps there's just a problem with the way you're experiencing our platform and we have to make it easier. And so that's when great design comes in because we're always trying to make it as user friendly, as simple as possible. So that's the goal.

to make people feel like it's so intuitive, it's as easy to use as an iPhone. I'm just thinking about how, I guess if I had a problem with Google, I would never actually bother contacting Google, right? Like it's just not something that it comes to mind because I'm like, obviously not gonna care, but in this case, you do care, and I can actually reach out to you if I have a problem with the product. So is that about how you,

onboard the client and letting them know that they can actually get in touch because you will proactively be able to do something about it. Totally. so we are interacting with our customers live in app with a widget and also we always share you know mobile numbers phones at the moment there's a couple of us on the commercial side that literally are on the other end of that mobile phone line so it's very high touch and probably at this stage not very well scalable.

but we also think it gives us such insights around the product that it is the best way that as a customer success team we can spend our time because if we hear things again and again that directly feeds in to my co-founder's ear who runs the product side of the platform and we talk about how we can then solve those problems. So it's a really quick loop. We like hearing where people feel like they have a question or are potentially stuck because that's where we move to next from a product perspective if we hear things

time, it gets escalated up the roadmap. So that feedback loop as a founder, I really value that for now we're extremely close to actually think it makes us nimble and responsive and ⁓ we get really good reviews on our ⁓ ability to help problem solve and responsiveness to feedback.

Yeah I think look

Doing things in an early stage company that are not scalable but are giving you so many wins and helping you navigate the product roadmap decisions, I think the benefits far outweigh the risks, but there's going to come a point in time where we're not hearing those things as you say, and then we can think about how we strategically improve that process. Yeah, I mean, I would love to hear more about how you kind of...

go on the decision making process what you really want to add structure to.

to operationalize versus what you just wanna dive deep into immediately just so can fix it. Okay, so this is one of the trickiest founder dilemmas. I actually hate prioritization, ⁓ but funnily enough, that's pretty much my entire job. Trying to figure out which thing is the most on fire to give your attention to next. I sometimes think of myself as a bit of a firefighter. I think that's probably just.

all startups.

What I have specifically in mind is that we have this feature that all our customers are asking us for. We have fully scoped it out. We're so excited to deliver it. We have extremely high confidence around how valuable this is going to be to the Delegence platform. And then we have a whole host of things that our existing customers are saying, you know, wouldn't mind if it did this and it'll just be a little suggestion or I wouldn't mind if it did that, another little nugget. And so you have to think to yourself, do we

spend a bit of time addressing those little nuggets of feedback and wisdom that our customers are giving us or do we go for that knock it out of the park feature and dedicate you know our finite resources to delivering this thing that we're super excited about and we know that our customers all love it's a really really hard process to filter that and we do that

typically at a cadence of at least once a month, we look at our want list of things that are up next and we have to reassess and filter. And so we do that by a couple of different methods. We...

prioritized by what we think is the most important, will then add how long we think that task will typically take. So we give a t-shirt size, like small, medium, large, extra large, in consultation with our tech lead. And he gives his input and opines as to how long he thinks that will take. And we also are always feeding into that loop what our customers are asking us for. So we've had a few customers bump up some things. I mean, they're not even aware. We're like, well, that was a little nugget that was a bit

further down that's going to the top of the queue. And we look at that again and again and we kind of debate internally about which one we think is the most important and that helps us navigate. That list is, it's not changing drastically I would say, like we have a very firm grip on. ⁓

the entirety of the list, but the order often changes. And I think that that's sensible and that's probably best practice if you wanna be as responsive to your customers as you possibly can, which is what we wanna do. Yeah, nice.

Fra (16:02)
what do you think is the advantage of being a technical founder?

There is unappreciated or is like dismissed more often than not.

Elena Tsalanadis (16:12)
being a non-technical founder, and we've encountered it when we went through our fundraise, is sometimes seen by investors as being a mark against your name. I can understand how having a technical founder is incredibly useful, like software development is expensive, amazing technical people do not grow on trees. However,

We're subject matter experts, our co-founding team. So we have so viscerally felt the pain of legal due diligence, this nightmare of a task that corporate lawyers have to do and done it ourselves. And so we are flexible as to the solution, but we really, really deeply understand the problem. And I think perhaps a benefit of being a non-technical founder is...

sure, I might not know how to build it, but I know what I am looking for and I am not necessarily constrained by how we get there. And so we enter these really interesting conversations with our technical team around potential solutions to problems that we bring them. And we're just not really fussed as to what that

I mean, not fussed is not the right way of putting it. We're not wedded to what the solution needs to be. And so we can be really creative. I think it means we're not confined or constrained. We know what we want that workflow to look like and feel and be, but we're really open and actually love being challenged and questioned by the team as to what we ultimately build. And I think the mark, we interview specifically for this, but we say to people like, bring your expertise. ⁓

Good ideas come from everywhere. We wanna build this intentionally psychological safe environment because we know that that's what the best performing teams are comprised of where the best idea wins every time. It doesn't matter if it comes from the most junior team member.

And sure, the founders need to have a voice in what that looks like, but it may be that that idea hasn't come from a founder, it has come from someone else in the team. So we really wanna uplift those

Fra (18:16)
I wonder if,

Because the ease of shipping products is gonna go close to zero, the perfect mix of talent in a team is gonna change. And I think I can see signals that tell me that that's happening. And I'm curious to see how that affects our relationship with VC.

Elena Tsalanadis (18:37)
I agree. I think the only caveat is it's industry dependent. okay, back in our early days, and you guys would know this, we, it started with a hand drawn piece of paper. Then we ⁓ went into a, like I designed something in Figma. Then what we did is we built something in a low code tool and we showed that to lawyers in every stage of the way we were getting feedback.

Fra (18:42)
For sure. Yeah.

Yeah.

Elena Tsalanadis (19:03)
My co-founder and I were reflecting and we were saying, with the rise of vibe coding, probably we could have shortcut all of that, grown together, gotten feedback or gotten some sort of a first version. The only caveat there is industry specific. So for us, we sell to major law firms.

Fra (19:08)
Yeah.

Elena Tsalanadis (19:24)
Number one, you can't put something in their hands that's half baked or kind of like MVP. They'll never use it again. It's got to be very good and very seamless. And number two is law firms are like banks. Like you have to have something so secure. And so for us as founders, we had to build a platform that was super robust and often low code, no code tools for firms, banks, and I'm sure like consulting practices, they don't meet minimum information security requirements.

So I think there's probably going to be this whole host of industries that can use these amazing tools that two, three years ago weren't even that prevalent. But I think there's going to be some niche pockets where they're still,

I mean, it'd probably be a good way to validate, to just throw something up and validate, think industry specifically.

Fra (20:11)
Yeah, I agree with you. I

Megha Sevekari (20:14)
you mentioned that there's a diligence, have stumbles of the week?

Elena Tsalanadis

Stumbles from the week. I introduced this at the startup that I used to work at because I read about it and I loved it. So the idea with a stumble of the week, we do this at our all hands, everyone brings something that they mucked up over the last week and we talk about it and we try and get better. It's not realistic to think that people don't make mistakes. Our thinking here was let's ventilate them and try and get better as a group.

If you're asking me for my stumble of the week, I have quite a hilarious one. We ran our strategy day recently and as part of that exercise we went back and shared with the team which has now grown our original business plan and in that 23 page very thorough and voluminous document we had, you know...

a handful of years ago written like we're not gonna be an AI company. We don't think it's there yet. We don't think the technology is there yet. And we looked at that and we actually highlighted it and put it on the screen and everyone was having a real giggle. We're now an AI company, Shock Horror. We think it has really changed. ⁓

Perhaps our assumptions at that time were fair and good, but what's so juicy and exciting is how quickly that technology has moved. And then we've understood how to implement that into our platform. So my stumble is that we thought AI wouldn't be there and AI is there and we're delivering value to lawyers. So the hubris of thinking that it wouldn't be is pretty classic. But it's so cool that you've like gone now, just adapted it and put it as a platform. Yeah, exactly. It's pretty exciting.

Fra (21:58)
I don't know if it's true or not, I never double checked. But the rate of success of founders that launch their business while they have kids is much higher than people that launched... I mean, guess because it's just like people that have kids is less than people that don't have kids, I guess.

Elena Tsalanadis (22:13)
I mean, what do know, Fra, is that investing in women founders and women led teams makes more money back on the dollar than male led teams. And we can get into a whole discussion around biases in the investment, you know, capital raise process, but investing more women, they're a better investment. To be frank,

the business kept in there for so long. We know that

Fra (22:34)
Yeah, great.

Elena Tsalanadis (22:39)
Look, a diverse team is what works. Men, women, different cultures, backgrounds, like that's what helps any business thrive. But we know that BCG and McKinsey Data says that for every dollar that you invest in a female-led business, you make significantly more back than male-led companies for a whole host of reasons. So, more women. And actually my personal goal is...

Fra (22:59)
they know that.

Elena Tsalanadis (23:05)
you know, as a card carrying feminist to improve the way that this system operates for women, which is not good or diverse groups in terms of raising capital. I think when I'm in a position to be investing, I should be supporting women and diverse investments because that's, think, truly how the system is going to change men and women coming together to make sure that we're investing in quotas that make sense and represent

Fra (23:32)
Definitely, absolutely. I'm with

Elena Tsalanadis (23:35)
I'm actually really

I'm really interested in how our biases just impact the way that we move through the world. I was giving a pitch, like at a pitch contest recently, and I was reading up on the fact that if I present the pitch or if my male co-founder presents the pitch,

He is going to be considered, same words used, exact same pitch. He's going to be thought of as more authoritative and more impressive. And so I've been wheeled along to a whole bunch of pitch contests and we've had some successes and not winning, that's normal. And I think to myself, I'm already starting back behind a gate just by virtue of who I am. I think this fed in for me personally in our investment process. I really...

took a step back because I know the stats around how few women obtain capital and let my male co-founder take the lead. And that's a real shame. our upcoming raise later in the year, I'm determined to be front and centre and share that load more equally because you can't be what you can't see. I think people didn't even necessarily know we were a half female owned company.

at that raise and there are a lot of investors now who have come up to me after saying, I actually didn't know it was partly your business. So there's just so much work to be done in this space. Unfortunately, I think in my opinion, the only way forward is having really clear quotas and investment mandates and asking investors to disclose the types of portfolio companies that they're investing in. I think without clarity and data, it's never gonna

better. So being really.

Fra (25:24)
I mean I thought it would have been an advantage. So I don't, yeah, well mean it's kind of like obvious but I don't know why it's not like, you know.

Elena Tsalanadis (25:26)
Totally. You would think.

Yeah. I think so much is pattern matching. There's these like the cut through ventures report. I always love reading it comes out every quarter or so. And they talk about the number of investments made. And so if you are an all male team, you typically have access to around 70 % of the available capital. If you're a mixed co-founding team that decreases to about 30%. So the fact that I'm a woman has drastically negatively impacted our chances of raising already.

And then it's even worse for solo female founder teams, so made up of just women. They have access to a crazy low number of capital. think it's between like two and 14 % on a good day. So it's really low and that's such a shame because there are such amazingly talented women-led businesses out there.

Fra (26:22)
Yeah,

absolutely, absolutely.

Elena Tsalanadis  (26:30)
So you think that, so do you think that it has to be an intentional, in the investment mandate quoted thing? Because people sometimes can be, have really weird responses around like putting it in the mandate or putting it in the quota. What do you think about that? Look, it's kind of like the gender pay gap. Like we've been talking about and had legislation that makes sure that women are paid the same amount of men as men. And we know that that's just not the reality. You know, there is a,

gender pay gap and I think there's a gap here with the way investments are made. I don't think quotas are perfect, but I kind of think they're the best shot that we have. We've seen them work elsewhere in other areas of society around getting female participation in government out of Scandinavia. I think there's this risk that when you have a quota, people then roll their eyes and say, well, that person only got that job investment or whatever it may be because they

form part of that group that we're

⁓ favored and prioritized. But also then I think it normalizes the fact that we're trying to edge towards 50-50 and have this representative pluralistic society, whether it be in the gender pay gap, investment, or politics. So I think my hot take is that's the best tool we have in our arsenal. But it is a discussion that we need to have, how we get there, because we're not moving quick enough.

Megha Sevekari

So you were talking earlier about getting the experts in when there's something that you might not know as much about. we've been until now, and Dilettants have been working together for almost a year now. So I'm first of all keen to understand how you think that's shaped or changed your journey.

Elena Tsalanadis

Sure, so I don't think I can understate the importance of great design for our platform and for our customer base. If you are trying to build a tech solution that is going to help people improve their workflows, speed up the way they do a task, it's got to be seamless. And I think a huge part of that is around design UX UI. So we've always worked with best in breed designers and

have always been told that our product's super beautiful and easy to navigate and that is so intentional. We want it to feel like you could open up diligence and not even need training and that's the goal that we've always had in mind. Working with the folks that until now has added an amazing layer of rigor to our design process. We talked about how like no one person can possibly be the expert of everything and so being pushed and prodded and questioned by the team.

has been so fruitful because we've been able to solve problems that perhaps we didn't necessarily foresee by working with such amazing partners. So I really feel so grateful that we've had this long and fruitful relationship together because the team have so deeply understood this really specific legal niche that we operate in, the type of customer that we're trying to help.

and the importance of putting a beautiful product in their hands. And we're so aligned on just delivering the best possible thing together. And maybe I'll say, you know, showing folks and getting a product in their hands early days and showing them something that felt easy and simple to use. I think that was part of the reason that we had so much interest and appetite even before we launched.

because we could show them something and say, like, would you use this? And they'd look at it and say, yeah, that looks really great. I'm excited to use that. In terms of getting that expertise, was there a reason that you opted for an external agency as opposed to getting someone in-house? ⁓ I don't think we had the design need to have a full-time team member. wherever we can, we've always leveraged working with experts so that we could flex up and flex down. Right now our needs mean

pretty stable and so it's been wonderful to have the expertise. mean, like what Until Now brings is that they've worked across a whole bunch of different industries for a whole bunch of different clients. So you're not just leveraging the expertise of an employee who's done design in one specific field. You're leveraging the expertise of a whole host of experts that are gonna chat about the best way to solve a problem and maybe draw on expertise that they've experienced across different industries and.

and experiences. So for us, it's been incredible because we can leverage that to enhance our platform together.

I mean, it's been really interesting because I think sometimes, people think that working with an agency or a partner is a negative because you should bring that talent in-house. And I think that there's probably a stage of company growth where it makes sense to have a team member who that's their full remit. But until you're at that stage, working with an agency that has a whole host of different skills, experiences,

and a different client base. mean, for example, we built a comment feature together and we were talking about how tech companies handle this, how different companies handle that, and that was able to get us the best solution. We weren't just looking at other legal tech companies that had a similar feature. We were looking wholesale at the market to figure out what helped our customers best. And so that's the layer of expertise I think

agency can bring to a startup.

Fra (32:09)
Yeah.

where do you see the engines to go in the future?

Elena Tsalanadis (32:13)
So

mission is to be the place that professionals run their deals. We want to be the centralized platform that helps them collaborate more effectively, scan contracts and deliver an amazing output for their clients. So that's going to be all folks that touch a data room to client report exercise. And we have global aspirations to expand.

to multiple jurisdictions. And so really what keeps us up at night is how to fit into the workflow of how that work is done with a beautiful tool, layering an AI where it makes sense and is super valuable and just improving the experience from start to finish. So we're really determined and have such high conviction in what we're doing and the way we're helping, for now lawyers, but soon many other verticals around delivering a data room to report.

exercise for their clients.

you can have a really good tool.

But it can be hard to adopt because people can be change resistant. And so we think about how do you embed enough? How do you solve enough of a problem that people want to keep coming back for more? And what's been really interesting since we launched our AI features, they were laid on top of our pre-existing platform.

So we already had something in market that was helping people like a workflow tool, imagine a monday.com for a specific type of lawyer. And then we were layering AI on top of that. And so

What I think our point of difference is here is that we had a platform that was solving a problem and then we were using and enhancing the way that a lawyer works with AI, so supercharging the manner in which they deliver work, rather than being a tool that perhaps felt like it wasn't necessarily already solving a problem and that had a risk of becoming shelf-ware. So I think a killer workflow fitting into the way someone does their job is going to mean that you

increase adoption and interest in your product and I think probably a lot of tech vendors out there, especially in industries like the law, are thinking about how they can ensure that people readily adopt their technology and it doesn't sit on the shelf gathering dust and so for us it was really deeply understanding the way the work was delivered first and foremost before coming to that ultimate solution that we put in lawyers hands.

I don't think I ever imagined that this would be my career path or career trajectory. I think it's so cool that we have these portfolio careers now where you start out as a lawyer and you move into legal tech and then suddenly you're founding your own company. I think for a long time I had imposter syndrome. I've...

which is probably something that affects a lot of women and men out there. I've always been surrounded by such clever people that I didn't think I was particularly smart and...

What's been really cool about this is starting a company, building something, it's so rewarding and purposeful and incredibly hard as well. But I think if you're that way inclined and you've got a good idea, like explore it. Once you get started, it's not that hard. I think that in the abstract, it can feel really hard. So maybe I would just encourage people to have a think about whether being an entrepreneur is for them because I think secretly in my heart of hearts,

think it was always for me.

Fra (35:52)
That's awesome, thank you.

Elena Tsalanadis (35:53)
Awesome. Thank you so much. You're incredible. Thanks for having me, guys.

Fra (35:55)
Thanks Elena. Thanks so much,

‍