S10E2 - From Harvard Law to SaaS CEO: Decoding the "Paperless" Future ft Shashank Bijapur, Spotdraft

Speaker A: Hey everyone. Welcome to the latest episode of the SaaS Sessions podcast. Today we have Shashank Bijapur on the show with us. Shashank is, uh, a co founder and CEO of SpotDraft. Founded by Harvard Law School lawyer Shashank and two Carnegie Mellon computer scientists. SpotDraft is an AI driven end to end contract automation platform for companies of all sizes. Right. So think of like a small startup till like, you know, big companies like Uber, Airbnb, everybody uses Spotdraft. Right? So, hey Shashank, such a pleasure to have you on the show.

Speaker B: Thank you. Uh, thank you and thank you for having me over. Let's get started.

Speaker A: Awesome. Great. Shashank, I gave a very short intro about you and Spotdraft. So why don't we get started with like, you know, getting to know more about you. How has your journey been through a lawyer to a SaaS company CEO and uh, building a company for the past close to nine years now. And uh, also getting more information about Spotdraft. And what do you guys do for somebody who have not heard of Spotdraft?

Speaker B: Absolutely, Sunil. So I was, and I'm an avid reader and uh, a lot of reading, a lot of uh, John Gesham got me to law school. And then post law school I was working in New York and at some point I was just looking around me and there was technology that was taking over most things, but lawyers were still slow, manual, and kind of outdated. And I kind of saw the opportunity in wanting to do something in that space. And that's where I started speaking to Madhav, my co founder. Madhav is a, uh, Carnegie Mellon computer science grad, one of the best hackers that I know. And he was like, man, this is a problem that I've seen and dealt with up close. And then we both came back to India independent of each other, wanting to. We were writing that startup boom in India, 2016, 17 were seeing a bunch of companies become unicorns. I remember when I had left India, I was scared to put my debit card on an online transaction. And then five, six years, five years later, when I was back in India, my mom was ordering stuff on Flipkart and uh, bigbasket using her card, right? So there was a huge change that had come. Uh, so what we knew that we had to build out of India. Madhav and I came back independently and uh, we caught up over a lot of coffee and uh, started really building Spotraft. So coming to what Spotraft does, every dollar that comes in or out of any Company is because somebody has signed a piece of paper. But that piece of paper ultimately is kind of low and it is, you know, paper driven and it gets lost ever so often. Where has somebody signed it? Where is it stuck? You know, did we use the right terms? Um, what did we sign in that other contract? So to clear that madness from quote to cash is what SpotDraft does. We are a contract automation platform. We help businesses create, manage and analyze and collaborate on contracts. So everything from can you please send me a contract getting that customized contract out of the door to, um, getting it signed and eventually renewed and getting insights out of it. That's what.

Speaker A: Nice, nice. And you mentioned like, you know, you were just researching about like, what kind of companies or what kind of industries are getting disrupted with like new age technologies. And like legal is where you felt, you know, or lawyers as a Persona, you felt are not disrupted yet. Right. So was there an aha moment that made you feel that, you know, like there needs to be like a dedicated product that is built for lawyers and, you know, or in this particular category. Right. So did you go through like a personal experience or was it just sort of, uh, observation that like lawyers or this category is like not disrupted yet, but you know, there can be something that is done here. As you were also going through the law school journey.

Speaker B: Yeah. So let's look at essential paper processes. Let's look at, let's say accounting. Let's look at photography and let's look at architecture. Accounting used to have books of accounts where people would actually have books of accounts. Photography. I don't know, Sunil, if you've ever been to a studio with a reel of camera and tried to get it developed in a dark room. So paper process and then architects would draw with their hand. Now look at what Adobe Intuit and AutoCAD have done to each of these industries. They've taken a essential paper process and turned it into software that now becomes more democratic for everyone to use and easier for the practitioner also to use. So today you and I can take a selfie, put a filter, put it on Instagram. Uh, and earlier we would have to take that into the dark room. Now let us look at what happened with lawyers. Lawyers. The greatest innovation that lawyers saw was a patch in Microsoft Word in 1993. And that patch that they introduced was called Track changes. That is when they went from sending faxes and actual handwritten red lines to, you know, Word documents and emails. That was in 93. Fast forward to, you know, 30 years later in 2023, what I was looking was people were still sending emails and still sending tracks, track changes. There was absolutely zero innovation that had happened. So that paper process remained a paper process for all practical purposes. So that kind of, at that point we were like, why isn't innovation happening here?

Speaker A: Right?

Speaker B: It is such an essential and ubiquitous necessity for every single company. But there is no innovation that happens. And the software that we saw was either too clunky, only enterprise grade. You know, it didn't look and feel like anything else that we were using.

Speaker A: Nice. That's a very interesting way to look at it. Great that you can explain it in terms that maybe I can understand what's the way that you saw. I totally remember taking those films. I think this was in my childhood, 20 years ago. Easily go to the rooms and then take few days to get the photos back. Now it's very instant. So interesting. So talking about SpotDraft, I think in one of our early conversations you mentioned that if like you know, take, take Bangalore as a city, right? Like anybody lands in Bangalore like every step of their journey they take right from you know, booking a cab to taking a pay like making that payment to the cab and maybe they're here for work so they go into like a WeWork or like a co working space. And you know, um, everywhere in that journey like SpotDraft is like hidden and helping the user or helping you know the, the process happen like seamlessly as you mentioned. So can you walk through that day in the life and show how and where like Spot Draft appears like behind the screens and behind the scenes so that people just know like hey, what's the power? Like you know, what's this contract like? Because like most of the people might think like oh, contracting only happens when like an enterprise signs a deal with like another enterprise. That's the most common understanding of a contract. Or maybe you are you know, taking a insurance or taking a loan. Those are like contracts as well. But can you talk about the more day to day, you know, use case of contracts that happen behind the scenes and how are they powered by?

Speaker B: Correct. So without taking customer names, I'll tell you exactly how the use cases are. So let's assume it's an airport.

Speaker A: Mhm.

Speaker B: At an airport. An airport. Essentially the core of the airport business is a leasing and a construction business. Right? So you're building new stuff and you're leasing that real estate inventory out. Every single contract is a unique contract that needs to be signed. And each of those contracts is a first originated in SpotDraft. Or ingested via SpotDraft. AI extracts key details. If it is ingested, if it is a contract that is created, then it goes through an internal workflow approval. Signature goes to the counterparty for signatures or negotiation. Every version that comes back sits there. Now that is an airport. Now let's look at someone like uh, a, you know, edtech company, their educators, they sign contracts using Spotcraft. It could be, you know, cab drivers that are uh, there. Their onboarding flow requires them to sign a bunch of contracts. That happens via Spotraft. So the fact that people who are listening to this either on YouTube or on any podcasting channel would. The fact that they, they're able to create an account and listen to you and me is because they signed a contract. But they actually it's called a click through contract. They said I agree to the terms and conditions. Now even that is powered by Spotraft. So we power every single place where there is repeated contract that is happening and then give it a nice little house for it to stay and for insights to come out of it.

Speaker A: Nice, nice. I think that's a good uh, way to look at it as well. And you know, making like I don't think people generally see it this way. Like when they are just accepting the terms, they are going through a contract. It's just like I know it's still a contract but still not a piece of paper. I personally would assume how contracts would be right? Not on a website or not on a uh, page that is hosted somewhere. And for SpotDraft, I know since you like all the founders have studied in the US and been in the US um, and most of the SaaS companies like in India, for them US becomes the primary market to expand into to get customers. So for you and for Spotra specifically, when you think about building India and sell in the US part. So what are some of the things and I did see on your website, right, like you have some amazing like US logos, right? So what some of the things that you did get right early in terms of like ICP and pricing, you know, positioning for uh, you know, for Spot draft, right? Because like yes, you are building a product for lawyers. But then I'm assuming that lawyers in companies won't have like buying power, right? But then like do you go to lawyers or do you go to like some other Persona? So like you know, setting up that entire GTM motion correctly while building from India is like a tough job. Like not many Indian companies, SaaS companies have like figured that out yet. So what was your Play here.

Speaker B: Yeah. So, um, let me clear the air here. The first thing is a lot of early stage founders come and you know, when they, when they reach out, one of the questions they ask is m, should we do ah, business in the US and my answer is close your eyes. The answer is absolutely yes. US is the largest homogenous market that is out there. Right when you want to sell and you want to build flywheels, you want to build it in an ecosystem that has a lot of homogeneity in it. And there are zero large SaaS businesses that I know of that have been built that are truly large and massive without, without having a U.S. presence and us being one of their key and primary markets. So the answer was clear that we had to go to the U.S. um, it is, we had to build a repeatable ecosystem. What made, what are the choices we made and how we landed up there? The answer is that we were, we lucked out where we knew that we knew when to stop, when we were failing. We didn't double down. You know, founders have this gambler's fallacy where they put a dollar and then they lose it and they want to put $2 and equip that then four. You know, and when you're tied to an idea and the way you want to build and uh, project that idea and you kind of don't really fully succeed at it, but you keep trying without realizing that you're failing, then that's a problem. And that is exactly what you know, we saw very early on in the first one and a half years, everything that we built was not usable at all. It had to be trashed. And we realized that what we were doing is not a scalable model. So with that I think the first thing that we did right was we realized that at that Point a sub 50% company sitting out of HSR Layout in Bangalore, a uh, NASDAQ listed company, wasn't going to start using us. That wasn't going to happen. We also knew from, you know, anecdotal advice as well as seeing some of this stuff firsthand, that working with extremely small businesses is a high churn, high CAC business and it is probably not scalable. And the ACVs were very poor for that. That kind of got us to the logical conclusion of mid market. And we said there is no enterprise grade software with a consumer look and feel that is affordable, that is modular and that can be used by the remaining 70% of the market where there is no software. So we had pressure from all sides saying we need to go enterprise. We need to go enterprise, but we remain truly mid market and continue to focus there. And I think that paid off for us. It paid off in the sense that our product, um, the blast radius was contained. Our GPM was very focused. Uh, Personas that we were operating in, each of these were very focused. For example, if it was a small business, we would have to probably go to a founder. If it was a very large business, then probably the procurement teams and the CIO would be where we would have our focus on. We knew that in mid market companies it is the internal legal teams that were making the buying decision. And we remained true to that and we continue to focus on selling to them. So, um, our Persona today is the in house legal counsel, which means the general counsel, legal operations. That's who we typically go and sell to.

Speaker A: Nice. And, and did your experience and your time at being Harvard Law and being a lawyer yourself, did it help like, how did it help you directly and indirectly with building a GTM motion? Right. Like I'm sure, like it would impact a lot on the product and the customer success and like, you know, the other parts of the GTM side. But uh, like you know, with respect to like gtm M. Like you know, you being a buyer Persona yourself, right. Often that helps you get to, you know, being, you know, wear the shoes of your Persona. Literally, like you have done that, right, because you are a lawyer. So how did that help directly or indirectly? And, and, and did it being a buyer Persona yourself in a previous life, like, did it help you, you know, avoid these obvious mistakes which many of the other founders might make because they were the buyer Persona themselves when they started their company.

Speaker B: So I think it has pros and cons. Uh, the pros is a being in the US There was a general sense of understand business is done. There was a general sense of understanding of that Persona. And the fact that I was a lawyer meant that I could use some of that knowledge to build product and kind of give early gut signals to, to how things should be built. So that was the good part of it. The bad part of it was it was only two years into spot draft I realized there was a word called GTM and what it meant. I didn't go to business school, I didn't go to, you uh, know, engineering school. So I had zero understanding, zero friends on either building or you know, going to market what's altogether. But there the thing that we probably did right, and that is a skill that every founder should kind of have. And I'M not saying I'm great at it, but I think we've been reasonably good at it. Is the talent density at Spotcraft. We've managed to get um, bunch of highly motivated, highly driven, uh, and people who really want to have fun and believe that this is their life's work, who work with us and they kind of navigated the ship in the right direction, uh, and helped us grow. So to answer your question specifically, uh, did my lawyer being help me? Yes, early days there was help m but it was counter, the counter effect of that was I didn't know a bunch of everything else, uh, that was going on in the company and I had to play catch up to that.

Speaker A: Nice. I think one more uh, thing to that, right. Like being a lawyer versus being a founder. Right. So how has your view on risk overall changed? Right. Because I think lawyers are typically trained to reduce risk. Right. And uh, as a founder you like daily, right. If not hourly or anything, you have to take calculated risks. Right. With different teams, different, you know, geographies, different instances. So how has your view changed on disc?

Speaker B: Great question. Sunil and I had a constant struggle with it and I maybe continue to struggle with it quite a lot. The so. So attention to detail and sending a perfect product out or a, you know, document out was what we were taught at law school with what I was doing when I was working. And then you take VC money and you say move fast, fail quickly, you know, time to market is very important. Get the product out, get consumer feedback, keep iterating. That just didn't jive well with me. In fact, for the first year we pretty much released nothing because, you know, product would be built, we would test, there'd be some changes we would have to make, it would go back to the drawing board. And that just kept happening. And at one point Madhav came to me and said, man, look, we need to go to market. This is not how we are going to succeed. Let's just um, you know, put it in front of users and get that feedback to iterate rather than with our own limited understanding of how things should be. Um, so it definitely was, it was an evolution for me kind of putting my lawyer hat out and wearing my founder hat and moving with speed.

Speaker A: Nice. And are there any specific, you know, frameworks, um, or you know, some, some tips or tricks that you probably have, you know, got from your legal training that you still rely on being a CEO and a founder?

Speaker B: I mean, uh, attention to detail is, is 1. So having micro information but not micromanaging it is another which is, it was a, it was, it, it was something that I had, I, I realized I had as a kind of a very hidden muscle and that's coming out now and then also evaluating risk really as you know, when you're getting into a business deal or you're getting into, it could be an investor or it could be a potential new channel that you want to do. The concept of how risk works kind of matrix is what I learned at law school. And finally the art of negotiation. I did a, uh, one of my courses at Harvard Law was at the Harvard Negotiation, uh, and Mediation center. And uh, just how to mediate and negotiate hard transactions, hard deals, hard M conversations. Those, those are things that I probably picked up in law school.

Speaker A: Nice, nice. I'm sure like these would be like very useful when you're negotiating those enterprise contracts for SpotDraft itself. Right. So and talking about uh, you know, SpotDraft as a company and category, uh, product and you know how AI is like impacting this whole category and your product. Right. So I think nowadays like OpenAI and Claude and all of these general purpose LLMs, right? Like they can definitely blog, like draft these blogs and emails and you know, all these other contents like fairly well. But um, you know, when it comes to like drafting like legal contracts, right. So where there are high stakes involved, right. So I'm sure like it's not like a hundred percent accurate. Especially like at SpotDraft when you mentioned like attention to detail and being perfect at all times or something that you're taught at law school. And that's one trait that you are kind of um, brought at Spot Draft with, not only with, in the product but also like with all the employees and pretty much everybody who's associated. Right. So like, you know, how do like, you know, what do you think of that? Like how does that shape your worldview where these kind of LLMs eventually will also start drafting these legal contracts. And what does that mean for Spot Draft and how have you integrated these LLMs within the products to make it like AI, uh, native or AI integrated.

Speaker B: So um, slightly long winded answer, but we actually started as a company that could go inside an NDA and identify the good, bad and ugly. Um, we had five very, very, very large banks who are our customers and we failed at it because the accuracy was very poor and the accuracy was very poor. Not because we were doing something wrong necessarily. Maybe that was a smaller contributor. But the larger problem was the promise of the product was way ahead of what technology could provide. So we were uh, quite a bit far away there. So we pivoted uh, to building workflows and an editor within the workflow so we could help get better data and understanding of how contracts work en masse. And then we've been training on LLM since almost 2019 was when Madhav, uh, has written a message on Slack saying, hey, we've got access to OpenAI's models, let us train our data and look at what the accuracy looks like. Uh, so this is not new muscle to us. This is um, uh, stuff that we've been building. But the leap that happened from 2021, 22 onwards to where we are right now is, you know, we had technology and this is to this probably an oversimplification, but we had technology that kind of knew grammar and school level stuff. Then we knew, you know, grammar, sentence formation, school level stuff and college. Now with LLMs you have like all the law school knowledge also built in. So you have a lawyer now all you need to provide is the contextual knowledge of a transaction or a company. Uh, right, every lawyer. So if, if, if, let's say Google and Spotcraft came with the same problem to the same lawyer, the advice would be different because the size of the companies are very different. So that is the context that Spotgraph provides. Now if you look at it from a language perspective, this is a very complicated space to be in, um, large language models, language being the operative word there. The deepest end of language that you can get to in any company is what a lawyer writes. Very few people who are not lawyers would have read a contract end to end, line by line and felt supremely interested in doing it. It is also the only kind of language that requires you to law school, pass the power, be interested in contracts to do it. And the only kind of language that goddamn costs fourteen hundred dollars an hour in the real world to solve for. Mhm. How do you take. So it is at the deepest end of language, it is at the most expensive end of language and it is a language that is needed in everyday business context by all businesses. So from a problem solution space it is a great fit. Now comes the question of accuracy. Again. If you go and ask a lawyer in house, lawyer in your company, if you go and ask me what is your biggest fear, the answer will be my biggest fear is me, you know, uh, a, uh, sales guy sending a contract out after listening to OpenAI. Because that is the worst kind of advice that you can get, I don't think in the next 10 years. And this is Kind of contrarian that we are going to have people who say that I signed a million dollar deal listening to a robot lawyer. That's not going to happen.

Speaker A: Mhm.

Speaker B: But the pressure to do more with less will always be there. So I think what will end up happening is a lot of the grunt work and a lot of the repetitive work will get automated by AI. A lot of the pattern understanding, you know, minor fixes that need to be made, AI will do. But a lot of the negotiation and the human element of going and shaking hands and closing the deal to get it sorted will continue to remain with humans that are involved in the loop and that is how business will be done is my kind of prediction on how legal will evolve.

Speaker A: Nice, nice. And just to follow up on the same thing, right, like uh, particularly on AI, not with replacing the legal workflows and the legal, like you know, the lawyers, but they definitely can assist. Right. Like be a co pilot when these lawyers or when these products are, you know, executing these workflows. Right. So in your opinion. Right. Last question before we move on to the lightning round. Right. So what does a great, you know, AI assisted workflow looks like for you in the next maybe like three to five years both for like, you know, lawyers who are, you know, sending the contract and for business teams who are, who received a contract and who just want to like sign and probably get ahead.

Speaker B: Yeah. Some of that future is actually here with SpotDraft and a product called sidebar that we are now doing ga of later this month where you can say hey look, uh, I am, I um, am let's say Ola. I have a cap aggregation business. It'll automatically go fetch all the laws that are applicable to you and it'll keep you posted on any changes that happen. Every new contract that comes in, it'll map out against your existing standards and tell you exactly where, what is missing. It'll also do a uh, historical analysis and tell you that hey look, these are the four clauses that get negotiated a lot. Why don't you go and tweak this language to get to seeing yes, faster. And then when a law changes and it affects you, it not only comes and notifies you saying hey look, a law has changed, but also goes into your contracts and says that Here are the 24 contracts that require changes and this is the change that is required. Click a button, it'll make the change for you. Right now, that level of work that's there, I think that is the future. Eventually I think the what will change and not Just for legal technology. But SaaS technology in general is the concept of go click on Start, create new, enter details in a form to get to a. Outcome will no longer happen. People are going to go to a chat box and say, create a new workflow with X and add the following three things to it, and it'll go ahead and create it. I think, you know, both from a user interface perspective, it's going to change in how we interact and the ability of what it can do will be far more deeper, greater than anything else that currently exists.

Speaker A: Nice, nice. I think that that's, that's good. And did you take the, uh, word sidebar? I'm sure, like, I've watched suits enough. Right. Like, side isn't. Sidebar is something like you go to the judge on the side with the other lawyer presenters, have a small conversation with them. Right. Something like that.

Speaker B: That's absolutely right. So again, initially, and, and I can, I can give the specific instance. I, I learned the word in a, uh, John Grisham book and that's how I picked it up. And maybe it was lying around somewhere.

Speaker A: Nice. Interesting. Moving on to the lightning round.

Speaker B: Right.

Speaker A: Like, I've asked like so many questions, but maybe three more. Not about like Spot Draft or like legal tech or anything, but just in general. So onto the first one. What is the one thing, Shashank, that has helped you shorten your learning curve?

Speaker B: I think being in front of customers and speaking to them and getting firsthand feedback has helped me a lot. Like it is there. There is a marked difference in how, you know, you would imagine when you speak to, you know, on a call, you speak to someone or you imagine how a user would use it. And there's a difference when you go meet them in person and they describe the problem. But it's not just on product, it is also on Persona, on icp, on go to market. Like, each of these things get solved by doing that. It could be at an event, it could be actually going and meeting customers. And I continue to do that pretty much every week.

Speaker A: Nice, nice. Onto the second one. So what do you know about your work now that you wish you would have known when you first started that

Speaker B: it is not a sprint, it's a marathon. And you've got to pace yourself and, uh, be, you know, uh, you need to know the longer goal. But, and, and, and, and pace yourself.

Speaker A: Nice. And, and the last one. Right. So what's the one AI tool that you use, like, every day and would recommend to, like, everyone who's listening?

Speaker B: Yeah. So the first one is obviously sidebar from Spotdraft. But that aside, uh, I'm a big fan of granola these days. Uh, I think it's made uh, my memory much better. It's helped me uh, get to my, to do tasks and uh, you know, made me more organized. Uh, and uh, they were also recently featured in New York Times, uh, 50 iconic technologies of uh, 2025. So any of you listeners who don't use granola and use any other meeting transcriber strongly recommend it.

Speaker A: Yeah, no, I use it like it's very good. We also use it internally and it's like insane. I think it's the way uh, there's so many note takers but I think the way it kind of like you know, takes the transcript and generates notes out of it, that's the um, that is the difference. Right? Like I'm sure like everybody has the transcript earlier I think that was a challenge where you know, you take an audio, convert it into transcript, but I think now everybody's on par with that. But then what's the way or how you take the transcript and turn it into a note which is meaningful. I think that is the gap that they've solved the best. So like better than Gong, Navuma and all of these other providers.

Speaker B: Hundred percent, you know, like getting to the what I describe it as the soul of the conversation. I m. Think granola does a great job at that.

Speaker A: Nice. By the way, this, this is also being recorded on Granola as on the side even though we are using

Speaker B: uh.

Speaker A: All right, great, great Shashank. It was a great, great conversation. Thanks a lot for taking time this morning and being on the show and sharing all these insights wonderfully. You know, excited to hear about your journey, about spot draft and how it is like impacting everybody's life in you know, different places but especially in Bangalore, like in like you know, in hidden uh, you know, processes that everybody goes in day to day lives but uh, don't know that hey, this is the tech that has been like, you know, supporting it on the back end. So great.

Speaker B: Thank you Sunil, thank you for having me on the show.