Vishal Sunak On Raising $161 Million To Create An AI-Powered Contract Management Platform

Vishal Sunak, CEO and co-founder of LinkSquares has raised over $160 million for his thriving startup. His venture has acquired funding from top-tier investors like Catalyst Investors, G Squared, Jump Capital, and Sorenson Capital.

In this episode, you will learn:

• Vishal’s transition from Brazil to the United States and his formative years in Boston
• His early career aspirations and the inception of LinkSquares
• The evolution and growth of LinkSquares, from a broad-spectrum start-up to a specialized leader in contract analysis
• His approach to company culture and team building
• The future trajectory of LinkSquares and its impact on the legal tech landscape.

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For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) that I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash. 

Moreover, I also provided a commentary on a pitch deck from an Uber competitor that has raised over $400 million (see it here).

Remember to unlock for free the pitch deck template that is being used by founders around the world to raise millions below.

About Vishal Sunak:

As CEO, Vishal is responsible for developing strategies aimed at assisting both corporate legal and finance teams with the review of their contracts. He works to prevent his customers from having to read each contract one by one.

He founded LinkSquares with the goal of building great products to improve how businesses operate. Prior to founding LinkSquares, he held positions in operations and product management at Backupify and InsightSquared.

In 2020, Vishal was named an Ernest and Young Entrepreneur of the Year finalist in recognition of his dedication to innovation and growth.

Vishal has a B.S. in Engineering from Northeastern University and an M.S. from Worcester Polytechnic Institute.

Connect with Vishal Sunak:

• Crunchbase
• LinkedIn
• TheOrg
• RocketReach

Read the Full Transcription of the Interview:

Alejandro Cremades: Alrighty hello everyone and welcome to the dealmakerr show. So super excited about the guest that we have today you know he’s saying a really amazing founder and I find that you’re gonna you’re gonna really see how inspiring his journey is he writing a rocket ship right now and. And I think that you’re gonna be learning a lot from his story from his journey on really bringing this to where it is today so without further ado. Let’s welcome our guest today bial sunak welcome to the show so born in Brazil.

Vishal Sunak: Hey Alejandro. Thanks.

Alejandro Cremades: Even though you know you’re you don’t seem to be much of a Brazilian when it came to the looks. Ah so so guess I walk through memory lane. How was life growing up bial.

Vishal Sunak: Um, oh come on man I got a 10 I got a tan today if.

Vishal Sunak: Yeah I was born in Brazil my sister and I were born in Brazil were were indian my parents were living there. We moved to America 1985 we moved to Rhode Island so I always wonder why we left San Paulo and moved to Rhode Island but for great opportunities ahead in America. I I grew up in Southern Rhode Island near the university of Rhode Island my dad’s still teaching their ph d electrical engineering. That’s how I grew up then eventually found my way to Boston which has always been kind of my home followed my older sister actually to Boston for education. Went to northeastster and studied engineering and then I been living in new england most of my life I worked in the defense industry in New Hampshire and then moved down to Boston and spent the last decade working in b 2 b software.

Alejandro Cremades: But you know it’s really quite quite a journey and and and then also you know how’s soft to your parents do as an immigrant to to the us myself. You know I understand you know what it takes and and and and and going you know to Brazil coming here to the us remarkable. You know how was how was it for you to be able to to experience you know this this this drive that your parents have to and and that had at that moment to really give you guys a better future.

Vishal Sunak: Yeah, you kind of grow up a little bit differently knowing that you’re the first kind of part of your family that is trying this great american dream and and so heavy focus on education is the key and pathway for a bright and successful future. Learning different things also learning a whole different culture like my parents didn’t really understand american culture. They grew up elsewhere all across the world and so it’d been a a good learning opportunity for all of us to kind of make the most of the american dream and and you know truly believe that it’s come. Come to fruition in many ways.

Alejandro Cremades: What an amazing country the Us the American dream right there with you now when it comes to computers. How do you get into computers.

Vishal Sunak: Well, my dad’s ah a ph d in electrical engineering. So you know getting that kind of exposure you you read books like outliers Malcolm Gladwell and you know they talk about people that just had that kind of built in advantage with how they grew up and definitely was was someone like that we had a computer early on. We had like a tri color ah Mac I remember using that and playing games on it and learning how to use a mouse and learning how to type ah 10 fingers at our early age and then getting into programming like getting into software getting into. You know, video games basic video games. It’s just kind of was like always a interest of mine like a tinkerer like building things legos erector sets building model rockets and launching them in fields near where we lived and it kind of always been me that like. Technology made the most sense for me I was most attracted to it I actually wanted to be an astronaut when I was a kid so unrealized dream there but ah, a good secondary dream with being a founder so I was kind of like always into it. And when I decided what I wanted to be when I grew up with high conviction seventeen Eighteen I was like yeah I’m going to study engineering study computer engineering do some more programming learn a little bit more and figure it out from there.

Alejandro Cremades: Now in in in your case I mean right away you got into product engineering and B Two B Software which has been you know, really the um, the the steps or the or the sequences that needed to happen for you to really get into what you’re up to now with Link Square. But then but with link squares. You know, like right before you got into it tell us what was that journey like of really understanding B Two B Software you know like what were some of those different roles that you experienced and then at what point where you like I think I got it. I’m really excited my time to Shine. Let’s go.

Vishal Sunak: Yeah I started in b two b software kind of not knowing where I would fit in given that I was building electronics for the military mostly radio frequency electronics for like fighter jets. So I had to learn everything I didn’t know anything about marketing really because the defense industry has no marketing They do all proposals from the government so to learn about marketing had to learn about how things get sold and then had to learn about how companies. Building and releasing software on a much more rapid cadence and so my early part of my b 2 b software journey was really learning the foundation fundamentals like what is a go-to-market program look like you generate leads. How do you nurture them? How do you warm them up. How do you pass them off to a sales team. What do they do with it. Well they give them a call. They do a qualification call. So. I take ah a lot of pride in in saying that a lot of experts taught me the game kind of hands on and I think that is ah a big part of the founder journey is when you want to be a founder and you want to learn and go do something There’s so much like rapid learning you’re going to do over a long period I’ve been operating the company here almost eight years and there are things that I knew coming in that were really helpful that kind of got the company off the ground like I had the basics of outbound and how to do outbound emailing and had that understanding and appreciation for.

Vishal Sunak: Content marketing and building software on Rapid release cycles and things like that and so a lot of my early career was just learning listening learning looking at how experts would decide how to just solve a problem or. Debug a problem or fix the business in some way those were the formative years for me for sure.

Alejandro Cremades: So then at what point you know did the idea of and link squares like really come knocking I mean how how was that like.

Vishal Sunak: Yeah I worked at a tech company in Boston about 120 people and in 2014 we were told that the company would be sold to a bigger company similar product a backup product. A bigger company came in and said well we need help on this acquisition and. Me having a role in operations really led me to be able to do everything and anything sales ops revenue ops marketing ops data projects saas metrics and so being part of the team that was helping with the acquisition. 1 of the requests was well. We need to know what’s inside contracts youve signed because we want to move you off Aws we’re using Amazon Web Services as the place we would store all this backed up data didn’t make sense to the company that bought us they had their own data center. They weren’t a user of this public cloud infrastructure. So they said we don’t want to pay your ews bill. We want to systematically move all your customers off Aws whose contract says that we can do it without their permission and they wanted to know that and they wanted to know that people who had any sort of exceptions or notice. And the answer to that question was impossible. We had thousands of customers. We have thousands and thousands of agreements signed some of them were all negotiated or third party paper using a big company’s paper for the contract of the terms of service. It was a real light bulb moment like wow this is a really impossibly hard project. It would take.

Vishal Sunak: Hundreds of hours thousands of hours to do this manually and also dealing with most of the contracts are in scam pdf so that was a real genesis for our first product for link squares what we call analyzed today which eventually through a lot of conversations. A lot of discovery. Ended up becoming a purpose built repository for contracts to be stored at rest and then an Ai use case to come in and read the contract tell you? what’s inside it and extract and create metadata about it.

Alejandro Cremades: So I guess for the people that are listening to really get it. Why ended up being the business model of link squares. How do you guys make money.

Vishal Sunak: It’s a traditional subscription based software ah users and then how many documents we’re storing in the analyze product and pricing has evolved a lot over the last seven years we do something called like a hybrid bundle which is we give certain stuff away and then. Kind of provide the ability for folks to pick stuff that’s important to them whether it’s api accesss or various types of integrations. Now. We have ah a very big product suite and so the the truth is that it’s sold in pieces or sold as a. Complete end to end system really catering to whatever the customer needs but very traditional user based value based pricing. Yeah yeah, what kind of extra bells and whistles people need. That’s how we price it.

Alejandro Cremades: How was the journey to for you from going to you know? Ah, let’s say the engineering side of things to now you know more the business side of things was that a tough a transition.

Vishal Sunak: Yeah, ah being Ceo is like the ultimate gaming context switching I mean even my day when you build ah a typical day of meetings I was just meeting with my cmo and then I have a meeting with my head of finance or my Cfo and. Then we’re talking about fpna planning and and then I’m into a product roadmap meeting and it’s just a lot of context switching and so the the formative years in Sas for me were just learning the other parts of the business I mean I understood software really well understood how it got made had to learn a different. Development cycle like a continuous development or continuous integration type model which not the hardest part to learn but but to be Ceo of a company now that’s almost 500 employees and have an amazing executive team. There are experts in every dimension you can rate them is really understanding deep enough. We can go deep on a topic. And kind of falling back on on those early years where I learned a lot about mqls and how it works and demand gen funnels and and how did we build a sustainable product roadmap and customer success programs and just learning through absorption but then putting it to work and then just. Getting smarter generally.

Alejandro Cremades: And now in this case, you know like the cells you know the early days of cells you know I’m sure that there was not easy and how do you go about it when you don’t come from a sales background.

Vishal Sunak: Yeah, luckily my co-founder had a lot more knowledge than I did I think my last time I ever sold anything was like a lemonade stand when I was a kid trying to hawk a hawk a glass of lemonade for a for a dollar on the side of the street I learned a lot about sales is not.

Alejandro Cremades: Ah, that’s a good start. Ah.

Vishal Sunak: The bravado of the pitch. It’s not the salesmanship of how you deliver the message. What some of it is but it’s mostly following a wellcided decide and defined process ah making sure everyone’s doing the work like if I do work and the other person does work on the other side. We’re coming to an agreement together in partnering together. They have to go do work on their end I have to go do work on my end and learning sales as a science now founder led sales I I always say you’re trying to turn like a d minus into a c plus. Just trying to kind of survive and learn doing a lot of learning It’s so important though for founders to not offshore the the revenue generation until maybe like a million ah arr or approaching a million at ar because you really need to learn. What people perceive about your product. Ultimately, you want product market fit to that market fit part is good to just keep on hearing it taking a lot of at-bats I mean conversion rates in the early days were pretty bad. Maybe 10 percent maybe less than 10 percent 5% so we needed to. To learn the muscle like how are you just going to build more at-bats right? We’re taking more and more at bats every single week. We’re getting better at the pitch. We’re getting better at the demo and generating more and more at- bats for us to continue to refine it and then getting into like closing. How do you close.

Vishal Sunak: Like we didn’t realize like security questionnaires would be a big part of it. So like how do you get through a security questionnaire I didn’t really know how when we got started but you know maybe now to my credit I did maybe 4 or 500 of them I can probably do them in my sleep still. And you learn what you don’t know and you learn it fast and I think that’s ah, a great part of the founder journey is you just have to learn everything really fast like you got a customer ready to buy get to get through their internal processes Procurement. You got to learn how to do with that. It’s just like continuous learning I mean I was still doing it now every day.

Alejandro Cremades: And now when he came to ah really knowing that you guys were into something with link squares I mean what was that moment where you ah when you were like I think we’re into something here.

Vishal Sunak: Yeah, 5 customers the first year we ever tried to sell it then we had it added another 25 the second year we had added a ah few folks like Bdr’s business development reps to just help us again. Generate more at-bats. We were just mostly concerned when generating more at-bats ah the year that ah we ah crept towards and then crossed a million a r and we had maybe 10 twelve thirteen people in the business. We had a cto eric still withney and and he was taking care of the engineering bill I hired a product manager he was running the roadmap I I was kind of starting to maybe oversee things a little bit more with doing a lot of the sales and at a million a r and yeah, that was. That was maybe like 50 customers or like right around 50 customers started to feel like okay hey we made it to a million now. Let’s get to 10 and the journey to get to 10 we did in 2 years and three months from 1 to 10 and really felt like we had learned a lot about. Where we live in a broader market too. Yeah, you can found a company academically you can read a bunch of studies and you can read a bunch of market analyses and you can say this is really great right? And we we really never did that what we did was was focused on solving a real business problem.

Vishal Sunak: And then kind of years later we figured out. Okay, this is contract management software. That’s the larger economy that we’re a part of we’re a piece of it. You kind of learn about what you’re trying to do and like where you’re trying to position the company and then ultimately. The year we did ah like 1 to 4000000 in 1 year we added 127 logos new logos in 1 year it’s like 30 people in the company and it was flying off the shelf. We really knew we had something and raised capital on the back of this success and kept going.

Alejandro Cremades: So how did it look like racing capital. How much capital have you guys raised today.

Vishal Sunak: Ah, hundred and sixty one and a half million five rounds venture capital.

Alejandro Cremades: My God that’s a lot of Zeros we shuttle. So how do you guys go about raising that money. What was the experience of going through all these different rounds.

Vishal Sunak: Yeah, ah, the same every round I mean the odds really never change. You have to be a pretty special company to raise venture capital money. You know most most venture capitalists as a job role is saying no for whatever reason. Small markets are not the right idea or don’t feel confident in in building a big business and so the seed round. Definitely you know opened my eyes to what the realities were raising real institutional capital. So we had done some friends and family. We had done some super angels before that. But then raising real institutional venture capital you almost don’t know what you don’t know and so that there’s always been kind of part of the learning is the first time you do it. You don’t really know what you don’t know and then the next time you do it. You’re better at it. Third time you do it. You’re even better at the fourth time you do it. You’re better the fifth time you do it. You’re really good at it and and it’s just like a learning thing but I mean the thing that I’ve learned the most is you only need 1 person and you got to try to take as many at-bats as you can and you got to do them all at the same time. No single threads. That’s a mistake I see a lot of founders make is they they single thread like 1 investor we’re going to go down the and try to walk down the aisle figuratively with 1 investor when really you got to try to walk down the aisle with 30 investors because when you get to the altar if you get 3 people there at the same point in time.

Vishal Sunak: A good economics of then how you can understand like do I have the best offer I saw in the market or do I have to restart the process from scratch on a single threat so multithreading do as many parallel conversations which just means like fundraising is a team sport. Ah. I I’m like the first baton of the relay race which is the big pitch deck and the vision and talking about the future and then the next card we turn over is like what we call supplemental information which I get my cro involved in my cmo and my my Vp of product and my cto and. Then they they fill in the rest of the business. We talk about unit economics and then after the term sheet comes out and is signed then I kind of take a backseat to my cfo and my chief legal officer. They actually do the financial diligence and then close on the dock. So. It’s really like a team sport takes a lot of sacrifice. And talk about like you know 20 hour days for a month and you burn out hard. That’s why I like I run the first part of the relay race and I’m happy to give the baton after the term sheet is in and signed and and you just learn it. You don’t even know what you don’t know a lot of fundraising is not real life. What you read about. And I believe that fundraising is not real life running a business is real life fundraising is just something you have to get good at do well it helps fuel the business like water in the body and then from there you go out and and you make the most of it with the capital you have and the vision you have you go put it to work.

Alejandro Cremades: Yeah.

Alejandro Cremades: So so for the people that are listening that are now you know thinking about raising money getting out there. Maybe for the first time what is fundraising and what is not fundraising.

Vishal Sunak: Operating is really everything.

Vishal Sunak: Fundraising is not what you read in tech crunch I’ll tell you that much fundraising is sensationalized as you know some monumental awesome achievement like build a business solve a real problem in this world. Build a real business. 1 that has traction or users or revenue or something you’re adding value to someone’s life especially in b two b you’re solving a business problem through software that has not been solved before or not been solved before. Well. You’re going to get far if you keep that front and center and don’t keep what you read about on Techcrunch front and center when you read about in tech crunch is built on a business that has something and I think a lot of the world got completely misbalanced in 2021 and and early part of 2022 where fundraising became real life and prices were obscene and valuations were insanity and and now we know in the world in 2023 a lot of it’s been corrected but you can’t be obsessed with like price. Ah and never never choose a 1 ah, venture capitalists offer versus another on price choose it on people. You are stuck with an investor who buys equity in your company. It’s harder to get out of like ah 10 marriages like you’re married to 10 different people you you could get out of that faster.

Vishal Sunak: Then you could get out of an investor that you know you don’t like the old I’m snowed in at ah airport could I survive with this person for overnight for 6 8 10 hours whatever you have to lends it with like people that you like and that means you should probably build relationships over time. And try not to do 30 day fiance where you’re walking down the aisle with someone you barely know or you don’t know how they will react you try to create a longer horizon which means a Ceo you got to get out there and talk to vcs all the time I try to do ah. Ah, meeting a week if not more than a meeting a week of just people are either reaching out to me or me using my network to try to talk to others just build that pipeline. It’s just like sales. So you’re going to do better if you have more pipeline you can do more sales. You know, be successful in your fundraises. You have more opportunities. Run them all in parallel and that’s the secret but fundraising is a team sport but it’s a mostly reflection on how well you’re doing today and how big your vision is and building a big company like how are you going to build a big company and and that’s that’s the secret to what it actually is and then getting back to work.

Alejandro Cremades: So well. Yeah, fundraising is on a milestone is a stepping stone So I’m right there with you now when it comes to vision you know and obviously this is something that you enrolled you know those investors and also the people that you have.

Vishal Sunak: And work it afterwards after it’s done.

Alejandro Cremades: To jump in because of the future the compelling future that you guys are you know, putting together there at the link squares. But if you were to go to sleep tonight Vihelle and you wake up in a world where the vision of link squares is fully realized what does that word look like.

Vishal Sunak: Yeah, we’re we’re really excited about ah in-house legal teams and that’s our buyer of our software in-house legal teams and we’re really excited about what’s going on with them regardless of what we do. And and that makes for really interesting moments in different markets as markets change the general counsel or the head of the legal team or the chief legal officer they themselves are going through a big transformational journey and so if I woke up and saw all of our vision come true. Like the general counsel has bought 7 8 ight nine products from us if you’re a big company and we’re really helping on the original mission which is we’re trying to move your business forward faster. We’re going to try to elevate the status of the legal team inside the company I mean I mean yes, it’s important. Software works and buttons and tables and dropdowns and features and this widget and this workflow and but if you go past all of that. The legal team are buyers desperate for data like their peers on the management team like finance and marketing and revenue. Engineering they all have data they they can all use data as a way to make their future better. My vision is that every legal team in the world uses a lins scores product to help make their life just a little bit better and more efficient use data and really modernize themselves much like their peers have done.

Vishal Sunak: And that’s like mission complete.

Alejandro Cremades: Now in this case, you know for culture I mean culture. Really, you know it’s It’s all about people and and and and the people that that you rallied here you know on this vision. You know it’s It’s also a big one is the culture that you’ve been able to ah to that You guys have been able to assemble there for Link Square. So. How do you guys think about culture and and I’ll show how how many people do you have now.

Vishal Sunak: It’s almost 450 now. Ah and and a lot of them live in the boston area. Maybe 3 under live in the Boston area and then we we run parts of our build team. Our engineering product design team throughout America and in that. Over twenty states so culture is like really interesting like everyone always asks I like oh what’s the culture of link squares and and and it’s it’s never anything that we wrote down in the early years right. But then over a longer period of time you realize that the people that did the best in the company could make it through hard times could help each other out could could lend an extra hand or do that extra 2% to to help someone out. Really codified and solidified. Maybe when we were at fifty sixty seventy people we kind of identified what that prototype person is who’s going to fit in with who we are. We didn’t start the company on founding values but they shaped organically and that’s definitely the best way to go forward with it is. Figure out who you are based on what you all believe is true and and so in link squares like we believe in being team first like like we’re always just helping each other out even in the early days hey you need extra hand with that. Yeah sure I’ll help q a this new feature with you.

Vishal Sunak: I’ll go q eight myself too even though I don’t have anything to really do with it I’ll click buttons and tell you if it works or not, you know we’re team first and we’re customer driven. We’ve always been customer driven right? Our customers have their hands on the steering wheel and we’re in charge of the gas pedal and and that’s how we got the company to where it is. We just. Been very disciplined on not trying to steer it to our own selfish needs and wants right? What we think is cool. What we think is cool. Doesn’t matter what our buyers think is cool. That’s really awesome, right? and and doing what you say operating high accountability and then being all in I mean those are our 4 company values is team first. Customer driven do what you say all in and the all in thing was really interesting. It’s like what does it mean to be all in It’s like we’re not going to stop in good times we’re going to go harder in bad times we’re going to support each other bring each other up and we’re not going to fail on this mission that we started out with which is helping every legal team in the world. Do something better than what they’re doing today which is not great using manual processes and email and spreadsheet. Let’s let’s fix all this together and we were those people and before we wrote it down.

Alejandro Cremades: I love that now. Imagine you know we’ve been talking about. You know the future too and and what I like to do is talk about the past but talk about the past with a lynch of reflection. So imagine if I was to put you into an time machine you know and I brought you back in time. You know, maybe to 18015 where you were now starting to think about maybe a world where you would you know take the leap of faith and and and go at it on your own and you had the opportunity of sitting down without younger visal and you were able to give that younger visal. 1 piece of advice before launching a business. Why would that be ny given what you know now.

Vishal Sunak: I would tell I would tell I would tell vichall that the sales part will definitely in the early days be the most valuable and the most hardest and learn everything you possibly can about how to sell us piece of software over Zoom. To another human and the tactics and the and the tips and the tricks how to do it more efficiently and how to get a ah defined sales process that not only helps you learn what to build next helps you create opportunities that are that are. Much more real and I would I would focus on that and the rest of it. You’ll learn over time. But if you can maximize maximize how much learning you have in sales probably could have got the company going even faster. You know sooner.

Alejandro Cremades: I love that so while Vihel for the people that are listening that will love to reach out and say hi. What is the best way for them to do so.

Vishal Sunak: For sure would love to do that Linkedin is the best send me a message connect with me I’m pretty active on there.

Alejandro Cremades: Amazing. Well hey we shout. Thank you so much for being on the deal maker show today. It has been an honor to have you with us.

Vishal Sunak: Thank you Alejandro really appreciate it.

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