Vishal Sunak - LinkSquares

How Vishal Sunak Took His SaaS From Zero to $10 Million ARR – with Vishal Sunak [281]

How Vishal Sunak Took His SaaS From Zero to $10 Million ARR

Vishal Sunak is the co-founder and CEO of LinkSquares, a contract management solution for in-house legal teams to draft, store, search, and analyze agreements.

In 2015, Vishal was working at Backupify which was about to get acquired. The acquiring company wanted to know what was in their customer agreements.

But Backupify had thousands of different customer agreements. No one knew what was in them and there was no easy way to get that information.

That first-hand experience of contract management and the pain points in-house legal teams face planted a seed in Vishal's mind of a potential SaaS solution.

Eventually, Vishal and his two co-founders (Chris Combs and Steve Travaglini) took the leap and launched their startup to revolutionize contract management.

They built a Ruby on Rails MVP with no backend. In other words, it was good enough to use for demos but wasn't a product that customers could use.

The founders then spent 9 months interviewing nearly a hundred general counsels. And it took them over a year to land their first few customers.

Vishal was worried about building the wrong product and wasting their money. So they wanted to be sure they were solving the right problem.

Today, LinkSquares does $10 million in annual recurring revenue (ARR), has a team of 70 people, and has raised over $21 million in funding.

I hope you enjoy it.


Click to view transcript

Omer Khan: [00:00:00] Welcome to another episode of The SaaS Podcast, I'm your host Omer Khan. And this is the show where I interview proven founders and industry experts who share their stories, strategies, and insights to help you build, launch and grow your SaaS business. In this episode, I talk to Vishal Sunak. The co-founder and CEO of LinkSquares, a contract management solution for in-house legal teams to draft stores, search and analyze agreements.

[00:00:39] In 2015, Vishal was working at Backupify, which was about to get acquired. The acquiring company wanted to know what was in their customer agreements. But Backupify had thousands of different customer agreements, no one knew what was in them and there was no easy way to get that information, that firsthand experience of contract management and the pains that in-house legal teams face planted a seed in Vishal's mind of a potential SaaS solution.

[00:01:08] Eventually Vishal and his two co-founders took the leap and launched their startup to revolutionize contract management. They built a Ruby on Rails MVP with no backend. In other words, it was good enough to use for demos, but the product didn't actually do anything so customers couldn't use it. The founders then spent nine months interviewing or trying to interview nearly a hundred general councils and it took them over a year to land their first few customers.

[00:01:38] Vishal told me that he was worried about building the wrong product and wasting their money. So they wanted to be sure they was solving the right problem. Today. Link squares does over $10 million in annual recurring revenue has a team of 70 people and has raised over $21 million in funding. Hope you enjoy it, Vishal welcome to the show.

Vishal Sunak: [00:02:02] Hey Omer, how are you?

Omer Khan: [00:02:04] I'm great. Good to get this setup and have this conversation. So let's start by my icebreaker. Do you have a favorite quote or something that inspires or motivates you that you can share with us?

Vishal Sunak: [00:02:15] Yeah, absolutely. I'm a huge, a new England Patriots fan. I don't know if that's a good or bad thing these days, but yeah. So I remember watching this documentary about Bill Belichick the coach, and he's got at hanging outside his office, prove it every week. And resonate really well with me obviously, cause I'm a Patriots fan, but just kind of the concept that like, “Good week, bad week next week, you got to keep at it”.

[00:02:41] And I've, I've always felt strongly about that quote. The other one is, is Marines – Improvise, adapt, overcome. Really kind of valuable for the, the entrepreneurial journey.

Omer Khan: [00:02:53] So tell us about LinkSquares. What does the product do? Who is it for? And what's the main problem that you're helping to solve?

Vishal Sunak: [00:03:02] Yeah, we're we're a contract management suite of products that has two main focuses. One is pre-signature. So a technology software that enables companies to draft. Agreements, collaborate on them, get them to the point of signing. And then after a contract has been executed either by hand or, or electronic signature, we have a post signature product that we call Analyze.

[00:03:31] And it's essentially like a purpose-built repository for legal teams to have a single source of truth. Of all their executed agreements, both historical and the new ones that are being executed every day. And there's an AI component there. We built our own AI to essentially save people a lot of time collecting metadata, like does the contract automatically renewed?

[00:03:57] Does it have termination for convenience? What's the limitation of liability clause say and actually create that kind of structured data, which is really super hard to collect. And that's a product that we actually started with in our pre-signature product finalizes is newer as a last year. So yeah, suite of products, helping in-house legal teams first and foremost, and then finance sales, success, account management, everyone kind of thereafter.

Omer Khan: [00:04:23] Great and then the company was founded in 2015. You've raised about $22 million so far. And where about you in terms of revenue.

Vishal Sunak: [00:04:38] Yeah, we were on 10 million of recurring revenue.

Omer Khan: [00:04:41] Okay, awesome. So how did you come up with the idea for this business?

Vishal Sunak: [00:04:45] Yeah, my co-founder and I, Chris works at a great tech company here in Boston where we're based called Backupify and I have I had an awesome job.

[00:04:54]I was in the operation, so I got to touch basically everything in the company and how it operated and sales and marketing and data analysis and SaaS metrics and finance ops. And I loved that job buying technology, implementing it. And so the journey of Backupify kinda pushed to the end and there was an acquirer.

[00:05:14] So this acquire had strong interest in buying the company. And I remember in one of the kind of first conversations where we met the acquiring company, they asked us what was inside our customer agreements. And I think we had six or 7,000 customers. Now, some of them very small, but kind of maybe a third or, or more than a third were pretty meaningful, a significant ARR.

[00:05:37] So what does that mean? Well, we have a subscription agreement with all of our customers that got red lined and got modified. So deviated from kind of the base template. This wasn't like a heavy. Click through business when you're talking about like, you know, negotiating bigger deal sizes. Also, we had huge logos that used our technology like Logitech and Yahoo and financial times and Waitrose, John Lewis, all these great brands, Netflix.

[00:06:04] And we were forced into using like third party paper, which is like a thing that big companies do to small companies is they put you into a subscription services agreement that they try to standardize with all the vendors. And it's nothing like yours. And you spend a lot of time and money trying to negotiate back to a place of back to center.

[00:06:24] So we didn't track like metadata about what we agreed to. And the acquiring company had like a really specific use case in mind. They were a backup company. They had their own cloud. We had built a whole business on like AWS. We were backing up like hundreds of billions of files like Google Drive and Gmail accounts like every day and using AWS.

[00:06:49] And so they said, well, I don't want to pay your AWS bill cause it's crazy. We have our own cloud. Can we move your customer's data without telling them and do it fast so we can start reducing our costs? And the answer was I had no idea, not one single person had ever thought of the day where we wouldn't use AWS.

[00:07:09] And well, they were like, okay, great. So customer agreements have the answers. Why don't you tell us which ones have free control? We can move the data at any time for any reason without notifying them. And anything else that that scenarios were agreed to, like you need to ask permission or you need to give us notice.

[00:07:29] So I stared down the barrel of this project, just trying to help out doing whatever I can, like what my job was. And we were pretty disorganized as like a series B company in hyper-growth mode. We didn't have one single source of the truth. Contracts were everywhere they were all mostly scanned PDFs so we're completely locked.

[00:07:51] Not searchable by control F or anything like that. And so I started breaking down this problem, like, okay, if we went and found all the contracts somehow, and we compare that against our ERP. So we knew who was active, you know, what could we do with it? Like, could we figure out what's inside them? Like, could we run like text searches or it could we, could we run something else?

[00:08:10] Like, that could give us insights or, or, or could someone read the contract somehow with technology and, and kind of the light bulb moment for us was that a, there wasn't, there wasn't anything out there like this that was solving this pain in contracts, post signature, like fully executed ones. We were completely unprepared to deliver.

[00:08:33] The answer without like a really painful manual review, try to read 6,000 contracts, which I felt impossible. And so that was a real trigger moment. Chris, my co-founder was working like count management customer success, and I kind of had this director offsite role and we said to ourselves, Hmm, this is interesting. I mean, we're not that crazy and we're not that different.

[00:08:56] We're, we're a VC backed SaaS company, maybe other people have felt the same pain. Like, do you know what's inside these contracts? Like, how do you keep track of them after they've been redlined? How do you keep track of third-party paper? And that was really the inspiration to go out and see if there was something there.

Omer Khan: [00:09:14] Okay. Great. So I want to talk about how you, you started to build that product and sort of validate it, but what did you guys end up doing with Backupify like did somebody, I actually have to sit down and go through all of these agreements?

Vishal Sunak: [00:09:27] Given the timeline of that acquisitioning and, and given kind of, you know, other constraints that we had, we ended up deciding that we should email all the customers and tell them that we're going to move them off AWS. And that was ultimately like one of the moments where I said to Chris, like, this is not the way there's gotta be a better way. And he agreed and that's how we got started.

Omer Khan: [00:09:52] Okay, great. So how long did it take from the point that you went through that experience with this acquirer, to the point where you guys decided that you were going to build a solution for this?

Vishal Sunak: [00:10:07] Yeah. Great, great question. So 2014, all of this was happening in the fall of 2014. And then that's when, kind of the discovery of like, Oh, maybe there's something here. And we were both working and we were both working at the acquirer company after the deal went through, like into 2015. And then we started thinking like, well, we've got to have more kind of conversations.

[00:10:31] And first off, like who is the buyer? Like who manages contracts. We didn't have a lot of knowledge because of the way that Backupify was operating. Right. We didn't have a lot of knowledge, like what do bigger companies do? And so through kind of enough, enough kind of subject matter experts in and around building companies, they, they pointed us to the fact that like, at real big companies or even companies that were like two times the size of Backupify, which is like in the couple of hundred employees, they have this role of general counsel.

[00:11:02] And it was like, Oh, the general counsel that's great. Chris, how many general councils do you know? I don't know any, I don't know any either. Well now what, so 2015, I actually left Datto. That company that bought Backupify. I worked at InsightSquared revenue analytics platform here in Boston doing sales analysis, sales analytics.

[00:11:27] And I saw a strong appreciation there, you know, strong as I've ever seen it for this kind of thinking that like, we're just going to cold email, anyone who could potentially be part of this target market. And I said, to Chris, I said, yeah. I mean, I think maybe we should run some cold email. I think cold email would be great.

[00:11:50] This would be a great strategy. Like we can go out to market this way. And so ultimately it took us, you know, from 2014 to November, 2015 when we incorporated, and then I kind of decided that I wanted to put all my. Put all my free time into this company, which was, you know, people responding to the cold emails and I wanted to start getting on the calls.

[00:12:12] So kind of hear what was going on. And so then I went, Chris had already gone full-time before that, and I kind of went full-time shortly thereafter, like in the start of 2016. And then we never looked back when

Omer Khan: [00:12:22] you started cold emailing general counsels, did you guys already have a product or an MVP at that point or you would just still trying to validate the idea?

Vishal Sunak: [00:12:32] Yeah, we, we built a clickable prototype, which was actually a Rails app. It was a Rails app that really didn't have a backend that was actually like writing and editing and deleting database records. It was mostly just a UI that, you know, felt really real. You're there, you can demo it in the browser. It's all kind of fake behind the scenes and that gave us enough.

[00:12:57] Kind of demo, like experience and to kind of communicate how we were thinking about features and get a lot of feedback. So yeah, we had something, it kind of became a lot more real towards the end of 2015 and then into 2016, where we actually started validating what the real product needed to do and actually then started building it.

Omer Khan: [00:13:20] So how much time did you spend building that first version? The one without the backend.

Vishal Sunak: [00:13:25] We had that up and running in, in about maybe a hundred days. Kind of early in 2015, and it's just like hire a UI designer, kind of think about pages and, and I'm an engineering kind of classically trained engineer by my education.

[00:13:43] So I love software and, and I kind of raised my hand to say, Chris, I got this part, you know, and, and we can, you can do more of the sales and kind of sales interactions, and discovery and feedback sessions with potential people who were, I mean, we weren't even thinking about revenue back then. We were just thinking about feedback.

[00:14:02] Like, can we get to a hundred, can you talk to a hundred general councils? And maybe after 100 general councils, we able to hear some of the themes that came out of it and it worked. And so, yeah, that's kind of how we divided things up.

Omer Khan: [00:14:16] So I'm curious. Why did you, why did you decide to build that in, in Rails instead of just using, you know, kind of like a prototyping tool, like InVision or something like that?

Vishal Sunak: [00:14:28] Yeah, I guess that's the nerd in me. I wanted it to, I wanted it to look very real. And there's nothing more real than an actual Rails app where like actual front end.

[00:14:40] Right. Right. I mean, yeah, it doesn't have a database, but Hey, it's real code. Right?. So

[00:14:45] It's real it's buttons and drop-downs and tables, and you can click different pages and it loads and I mean, that was important kinda to make people feel like this thing was real and they could have it, you know, would you pay for it? Like I thought that that was an important thing in the early days. And we've used that same sort of strategy and kind of other, other products and initiatives that we've done inside the company just kind of create like a minimum demo mobile experience and be able to communicate.

[00:15:15] You know what it is you're doing and what it is this thing does or how it can add value and how it can change your life if you start using it. And now there are moments where people would be like, can you click that button? Like, what does that button do? It's like, you don't want to see that. That's fine.

[00:15:29] Then I'm moving on in is a button to nowhere. All right.

Omer Khan: [00:15:33] So let's talk about the, the cold email and, you know, I think we've at least on this show, we've talked about cold email from time to time in the. I don't even know which episodes it was, but there's obviously, you know, it's kind of a science and art to doing cold email and a lot of persistence required to sort of make it work.

[00:15:57] What was the experience like you guys? So when you sort of said, okay, well, we don't know any general councils, we're going to start cold emailing them. What was the initial response like?

Vishal Sunak: [00:16:11] Yeah. So we use a 40 email sequence and Chris, and I would kind of go interchangeably on sending it. And we use Tout app the only company in the sales enablement space that would sell us one license.

[00:16:28] So had to, to TK at ToutApp the founder there who was, was nice enough to sell us one. And so. Yeah, the email sequence was pretty straightforward. First email was like, hi, I'm Vishal I'm CEO of this company in Boston. And I used to work at a company that looks and feels just like yours, a venture-backed SaaS company.

[00:16:48] And here's the struggle that I had, which was like, we didn't know what was inside our executed agreements. Like, does this look like you, does it sound like you, would you be interested in chatting for 20 minutes? And so, I mean, again, we weren't even really looking for revenue right-on kind of the early side of.

[00:17:06] No 20, early, 2016, and late 2015, we weren't even really looking for revenue. It was more like. Can we hit this internal milestone of like talking to a hundred general counsels and validating that they have this pain. So we can then put our foot down on building the real product. And so that was our strategy and it worked amazingly well.

[00:17:26] I mean the first week, like I think five or six, six general councils of like unicorn tech, startups, like name brands, all replied. And I remember like, high-fiving Chris would be like, we made it bro. Like, that's it like, it's working, it's amazing. And we, we didn't close a single one of them and still have it, but they're on my most wanted list to get them back.

[00:17:53] Yeah, it was, it was like the feedback just pops like so instantaneously, like, did we get so many replies off the first email? And people were interested in hearing more and saying, yeah, no, I agree with you. And then say, Oh great. Can we set up a time to just chat and just kind of learning? It's a lot of learning.

Omer Khan: [00:18:15] And what did you learn from those conversations that, that helped you because the thing was, this was driven by a situation where, you know, a company is in, in conversations about a potential acquisition.

[00:18:29] But it sounds like that's not the only use case for the product. Right. So, so you discovered something else from these conversations.

Vishal Sunak: [00:18:38] Yeah. And so when we were getting on these calls or these general councils, what we were learning was that they, they didn't have like a purpose-built system that was feeding them insights into like executed agreements, making their life easier.

[00:18:54] And. That was a real light bulb moment because that's like a niche that you can go and own. And we learned that like, most people are storing their contracts. Like on-prem shared network drive something cloud-based like box, Dropbox, Google drive that kind of provide the, the repository though doesn't add any other extra value?

[00:19:16] Right? And so that was awesome. That was just amazing learning. We saw it super clearly. And then we started telling them about like, what happens if you could have a single source of truth and you could have like analytics and it's, full-text searching and I'll take care of your scanned PDFs and get to great kind of digitized files.

[00:19:38] Like, could this help you when you needed to go and review them? And kind of, we also learned why people review their contracts. Like there's a change to a lower standard, like a new privacy, a new privacy law comes out like GDPR or something like that. And that then creates a trigger point inside the company where they have to go and read all their contracts and see if they're compliant to this new law issue amendments or, or redo the contracts.

[00:20:10] And so it was awesome. I mean, those early days just kind of validating what the pain was kind of what they were using seemed like complete greenfield space. The other thing is that we learned that there was an applied AI artificial intelligence use case where. People were, were kind of suggesting, like, what can you just tell me what the effective date is it?

[00:20:34] Can you just tell me when it renews and can you just tell me if it has automatic renewal or can you just tell me if it has termination for convenience? And can you just tell me kind of reading between the lines translated into like a machine learning type of technology, which. Then became the analyze product that we add.

Omer Khan: [00:20:52] So was there any, any sort of competitors out there around that time I'm trying to figure out was, did you get such a response from people from the cold email because. This was something they would just, there was no other solution out there, or they were sort of, they were, but they were kind of struggling with sort of half-baked solutions, which didn't solve the problem very well.

[00:21:18] Like why do you think they, they seem to respond so well to your cold emails, even though you weren't able to convert a lot of them.

Vishal Sunak: [00:21:28] Because contract management is not a new topic category. It's probably 20 years old, 25 years old and kind of the legacy kind of generation one players. They focus their entire software offering pre-signature.

[00:21:46] So it's like the workflow around getting a document to the point where it can be signed. We said to ourselves, we're going to start with the use case that we know, and we felt the pain on. Which is post signature. And so, because they had heard of contract management software, some of them have been tried the pre-signature piece.

[00:22:08] We're able to validate that, Hey, did the pre-signature piece help you ultimately with the pain that I think you have? And they were like, no, it didn't. It actually did something that was adjacent to it, which was helped us quote, unquote, work more efficiently to get a deal to the point that it can be signed, but it didn't help with the, like, can you help me understand what I've already agreed to?

[00:22:32] And like what's in the 25,000 contracts we've already executed in the lifespan of the entire company and what's inside all of those, which that wasn't the point of those kind of precinct or tools was to help you make a better future, help you make a more efficient future, but not looking into the past. And that's really where we found the gold.

Omer Khan: [00:22:51] So I think some people, many people, if they had an idea, they built this prototype and send out cold emails and got this sort of response back that people were, were interested. They wanted to talk. It kind of feels like, like you did right. You were like, yes. See, Hey, high five we've we've we've made it kind of would make sense to just say let's, let's build a product as quickly as possible and see if.

[00:23:18] People will pay for it. What was it like, why did you guys decide that you were going to take longer? Why did you, how did you come up with a number? We want to talk to a hundred general counsels before we sort of go to the next step.

Vishal Sunak: [00:23:34] It was the fear of spending capital that we didn't have basically running the early days off of our own savings about building the wrong product.

[00:23:47] And sinking all this time and all this money into the wrong products and just being really hypersensitive around the fact that one, one person isn't enough, five people aren't enough, 10 people aren't enough. 50 people aren't enough, like a hundred people. You'll be able to see trends. And the trends are the things that we want to bet on.

[00:24:10] And the trends in aggregate with sample size of greater than. You know, 75 or, or equal to a hundred can help us validate that we're not in like a big competitive pressure cooker, like build this product or, you know, I get deported from the country. Like, like it was more like we wanted to be smart about it.

[00:24:33] We want it to go slow and we wanted to validate, we were headed in the right direction. Now a million things have changed in a good way. You know, since, since that journey first started, but we at least knew the line of bearing approximately to where we needed to head to. And we're still relatively on that line of bearing.

[00:24:54] And I think people rushing to wanting to build something and that's, and that's cool, right? Like, Hey, instead of a clickable prototype, if you've got the time and you got the resources and you've got the cash, you can build a whole full-blown web. But if you get it wrong, it's pretty defeating. It takes work. You gotta rework it. You gotta, you gotta go back from scratch. And that's why, like, you know, tools like InVision and the other prototyping tools exist. So you don't have to make that big of a commitment, but we were feeling like the, the feedback was coming, starting to come pretty fast towards the end of 2015.

[00:25:30] And we were starting to kind of assemble that critical knowledge that we needed because now, like it's, it's 2021 and we've got 70 people at the company. Like we can go. We can go fast, like, like going fast now is easy. Like we got cash in the bank and people here, we can go fast on anything now, but we, we wanted to set ourselves up in the right way to do that.

Omer Khan: [00:25:53] So did you hit your goal of doing a hundred interviews or having conversations with a hundred general counsels?

Vishal Sunak: [00:25:59] Pretty darn close? I'd say.

Omer Khan: [00:26:01] How long did that take?

Vishal Sunak: [00:26:02] Probably took from, I'd say the summertime of 2015. Kind of summertime 2015, like into the fall of 2015 until like March, April, 2016. So just under a year, maybe nine months.

[00:26:21] I mean, we did it for like nine months and that's a long time when you're sitting around like basically hearing. People give you feedback. I mean, hats off to my co-founder Chris, who actually has a ton more patience than I do just personality-wise. We hung in there and we stuck around. Right. And there's a big story there about sticking around and learning and making a good bet when the time is ready to make it.

[00:26:46] And will you guys, during those nine months, were you going in and kind of refining the, the Rails app, the prototype or were you just kind of saying, let's just keep testing this thing and we'll just focus on the conversations instead.

[00:27:02] Yeah. I, I spent my time building the prototype and then ultimately the first web application that. Now we're still in production and that's a foundation kind of nights and weekends while Chris spent time during the day kind of gathering feedback, writing these summaries kind of, Hey, this is what I'm hearing. Like, take a look at this. Like, what do you think about that? Like how can we capture this encapsulate, this kind of feedback into the product?

[00:27:28] And then there was a little bit of crossover point where the real live application was starting to be built. And the prototype was kind of starting to age itself out. And then eventually we just kind of switched over, like in 2016, we just kind of switched over to using the real demo bowl experience.

[00:27:47] And so the prototype served itself. Well, probably six months, seven months. I mean, we used it for a while.

Omer Khan: [00:27:52] So let's talk about how did you get your first 10 customers? Where did they come from?

Vishal Sunak: [00:27:57] Cold email and one referral. Our first customer, I knew the CEO, the former CEO. She had sold the company here in Boston. And I emailed her and said, I think you're coming in and be a great fit. Who can I talk to? She wasn't operating anymore. She wasn't CEO. So she sent us over to the CFO who, when we walked in there, it said, I have this exact pain. Like we just have to do this big contract review exercise. It was so painful.

[00:28:28] He asked me if we were reading his emails, like in a jokingly way. And Chris and I looked at each other and were like, yeah, this is great. And then he asks us how much it costs. And we just said, it's a thousand dollars a month. It's $12,000. That was it. That's $12,000, $12,000. I remember that moment. Yeah.

[00:28:46] And so kind of one to two cold email and like the first 10 were all cold email and, and we really wanted to prove it like the first one. Hey, that was cool. That was like an inside thing. We had to go prove it with the company, but we got kind of a referral. Can we get 10 people we don't know. Didn't do us a favor. Didn't write us an email. We talked to them, we work them, we close them and kind of validated it. And once we had 10 kind of early in 2017 , early in 2017, we're able to then really think that we could get to a hundred or more.

Omer Khan: [00:29:25] And then those, so one was the referral and then the other nine from cold email, were they all people that you'd had some kind of conversation with before?

Vishal Sunak: [00:29:34] Never completely net new, complete strangers, no friend of mine, or a friend of mine dad's who was a general counsel, nothing complete strangers in the first 10. That's what we really wanted, what we wanted. This is a great article. Jason Lemkin posted about Initial Traction is 10 unaffiliated customers and I had read that and said, okay, well, Jason's pretty smart. He knows what he's doing and let's, let's shut it go for 10 this way.

Omer Khan: [00:30:01] That's awesome. And then like, ballpark, like how many customers do you have today?

Vishal Sunak: [00:30:06] Over 300.

Omer Khan: [00:30:08] And have the majority of them come through cold email, because I know like these days you're doing a bunch of other things or an acquisition, but

Vishal Sunak: [00:30:20] Yeah, we're trying to try to balance out the, the kind of the lead sources, but outbound is still really effective. Outbound is super effective with our buyer in its role. I mean, people listening to this show should be unafraid of using outbound. It has great, you know, cost of customer acquisition benefits. And, and also you get a lot of like real-time feedback in the market, like what's going on. So yeah, we still use that.

[00:30:47] And now. Yeah, we get a strong, strong customer referral network as kind of the word gets out and kind of the review platforms and SEO. And if it wasn't a pandemic, I mean, we love a good trade show of the general counsels are a fun bunch. We love sponsoring at trade shows or the fund deem and, and engaging with them. And those all been kind of amazing channels for us.

Omer Khan: [00:31:10] Yeah. I mean, cold email is great. If you're getting the kind of response that you guys got it's it's not so much fun if you're, you're getting no responses, just you're hearing crickets or people are telling you to, you know, get lost. But yeah, I think there's definitely some lessons herein, in terms of, if you are not getting an enthusiastic response from people one, maybe it isn't the right problem. Maybe you're not articulating that problem the right way, or maybe you're not talking to the right person. And it's kind of figuring out, I think, a combination of those three. And it sounds like you guys kind of had, had some luck with that when you, when you started out.

Vishal Sunak: [00:31:53] Yeah. The, the journey to like product-market fit requires like a little bit of luck. It's not all like the spreadsheet and like, you can't, you can't make a spreadsheet of product-market fit and say, I'm going to do this and do this and this order, I'm going to make a Gantt chart. And then we're going to have product-market fit. I mean, it takes a lot of like iteration and a lot of, a lot of bobbing and weaving a lot of like listening to what you're saying, what they're saying, what their challenges are, how they buy, what tools they have, like kind of keep, keep working on it.

[00:32:23] Right? It's a continuous work in progress. I mean, even the company today, a continuous work in progress as we continue to expand our knowledge into our ideal buyer. Right. And that's just the curiosity, the intellectual curiosity to keep learning and never kind of feel like, you know, it all, that's been extremely valuable for us.

Omer Khan: [00:32:44] So let's talk about some of the struggles that you guys had along the way. You know, you were a first-time CEO with this business, and I want to kind of understand, you know, what that experience has been like. And then also, maybe let's start talking about raising money first. Like when you guys decided you want to go and raise money and you know, you've got some.

[00:33:07] You've got some traction here and, you know, your target market seems to be pretty excited. It seems like a slam dunk that raising money isn't going to be that hard. What was that experience like?

Vishal Sunak: [00:33:18] Yeah, we did three rounds of financing, so a pre-seed, seed and then series A most recently last year until the first time we raised as part of like our pre-seed financing starts with Angels or it start with smaller checks, like try to raise half a million dollars.

[00:33:37] And, and just kind of start out on the journey right. Kind of I had to also build my own knowledge of like Venture Capital and what it is and how do you get it and how do you talk to people? And like, what's the whole point. And, and I had to kind of round out that knowledge. And so I used the really strong network here in Boston, so amazing, amazing, like multiple-time founders and serial entrepreneurs and sold their businesses that came in.

[00:34:04] And really, I call them my sensei's. Like, you know, they were able to teach me the game and like also teach me like, okay, this is what this means. Like when, when they say this, they actually mean that. And like, here's the, here's kind of the insiders inside about raising capital. And so when, when I was first starting out, I thought maybe Venture Capitalists do like 50:50, like first-time founders and kind of repeat founders or people who are, are name brands or worked at Google or whatever. It's probably like 98:2 or something like that or 99:1 skewed towards people they know, you know, multiple time around though. I think it's changing these days.

[00:34:43] That's kind of what I saw and felt. Right? And. It was really around. How do I tell my story? I'm a no-name yeah, I worked at a great tech company in Boston suite. I wasn't the founder, but I was like employee 30. How am I going to walk into a meeting and tell them that this is the bet that they should place and, and you should bet on me.

[00:35:06] And so I thought to myself, I didn't go to any Ivy League schools though. I went through a great undergrad and Northeastern. I had some experience working in SaaS companies. I definitely knew the operation of a SaaS company. I knew the metrics really well because that was my job. But how am I going to tell an undeniable story?

[00:35:23] So like you can hate legal technology and you can hate contract management and you can think it's dumb and you don't want to sell it to the general counsel. You don't want to be involved with a company like that, but you're going to have to take the meeting because I have a sweet-looking ARR line. And I'm going to prove it every single day that this thing is real with customers, with revenue, with traction, and I'm going to run a great business.

[00:35:48] And so the second-order metrics, CAT, CAC, payback, sales efficiency, lifetime value, all that stuff, gross margin because all this stuff is going to look so good to prove to you that on the CEO, you should bet on this is a company that's growing really fast. We found something we're onto something, come help me grow it.

[00:36:06] Right. And that was always the kind of strategy that I took in. Every founder has to tell their story, like, why, why is it you? Like, why, why are you starting a like Figma? Like why did you start Figma, well, like I was a designer and I have this subject matter knowledge, or I know something about this space that other people don't.

[00:36:26] And we kind of said to ourselves, we know something about this space that other people don't, and I'm going to prove it to you with people signing order forms and paying us. That's how I'm going to prove that this thing is real is this is not an idea. This is a real business.

Omer Khan: [00:36:40] So what kind of pushback did you get when you started talking to two investors?

Vishal Sunak: [00:36:47] A hundred, a hundred different reasons, and still to this day, a hundred different reasons. Some of the ones I mentioned, I don't like legal technology. I think it's, I think it's got too many competitors in it. I don't think it's as big of market size as you do. I don't like this part of your story or, or back in the day, you know how you compose the team.

[00:37:09] I wish you were selling six-figure deals. I wish you was selling $20 deals. I wish. You were, you were out market down market. I wish you didn't have to sell. I mean, all of these reasons, right? Like we're just not interested. I have, I mean, the most blanket answers, we have no interest in this space, this product, AI, this stuff this way, just have no interest in it.

[00:37:31] I don't have a, I don't have a hypothesis Omer, that's the line. Like we don't have a thesis on this space. I mean, cool. See you later onto the next one.

[00:37:41] Omer Khan: [00:37:41] And then how long did it take before you were able to raise, raise the money?

Vishal Sunak: [00:37:45] Yeah, pre-seed found a great family office person that rang the bell and the New York stock exchange twice in their life companies that they started from scratch.

[00:37:53] And so. On a chance to meeting that was how we did kind of our first million dollars into the business to capitalize it, which, you know, still, still stay in touch with him. And he's such an amazing operator, a lot to learn from. I got my first institutional money, my seed round in 2018 and running. I went out to raise $3 million.

[00:38:15] We ended up raising like $4.8 million. And that was fun and really kind of felt like the company was arriving. And, you know, we were almost at a million ARR then and feeling like we knew kind of, some of the components were in place and that was able to hire, you know, more on the management team, kind of round out the skill set, bring on CTO, bring on VP of product, bring on CRO, continue to help round out the management team.

[00:38:39] And then, you know, going out for a series a, we had gone like. Like a one to like 4 million ARR in one year. It was a while this year in my life, I got like one to 4 million ARR and I use that growth basically a quarter ahead of when the pandemic hit to go and kind of like raise our series A and you know, fortunate to find a great partner who believed in the vision and jumped Capitol, lead our series A.

[00:39:08] And so it took a lot of stone turning, you know, it took a lot of pitches, took a lot of at-bats. And that's like a big secret to this thing is you gotta run it like a sales process, like top of funnel, you know, deal stages. I actually use HubSpot CRM when I'm raising money to just give me a holistic kind of Kanban list view of like where all these conversations at, like, am I past the first call on my, in initial diligence?

[00:39:33] Like, like, are they at the end? Are they had late-stage diligence? Like where are they? Like, keep on adding more, more people in and keep a big list of, of investors just updated. You know, twice a year, like, Hey, here's the update about the company going great. This, that, and the other thing we built this, we hit this target and we're here, we're there.

[00:39:52] And then next time when you're raising capital, it's not like starting from hello. I'm Vishal. Nice to meet you. I've never met you a day in my life. It can be more like, Hey, we've been talking and I'm raising capital now let's chat.

Omer Khan: [00:40:05] So you so said earlier that, you know, you're, you're a self-confessed nerd and loved the, the coding aspects of this and now you you've sort of transitioned and, and seem pretty comfortable in, in the CEO role. What have been some of the, the difficulties or struggles you've you've experienced in, in sort of growing into that first-time CEO role?

Vishal Sunak: [00:40:30] Yeah. One of the things you got to learn, like is that it's my job to hire the best person to work for me, the best head of sales, the best engineer, the best head of success, the best head of product.

[00:40:45] Right. And it's my job to like, tell them what's important. Like, these are our goals. Like this is what our board has feedback on for us. Like the things that we should be thinking about. Here's our plan, here's our goals. This is what I care about. These are the things at the end of the year that what we need to achieve and all the reasons why.

[00:41:06] Right. And then for me to not tell them how to do it. Like, even though I might have opinions, I might have thoughts. I may, I, I, I'm an engineer. Like I have thoughts about our product bill. I'll have thoughts about the way things look like, but try as much as I can to never talk about how they do it. If they're an expert and I've hired the right person, they're an expert, they're going to know how to do it.

[00:41:31] Cause that's their job. Right. And it's mostly my job to, to prescribe the, what you get out of the way. And be there to cheerlead them and coach them and, and, and push them along and help them when they're stuck, if they need help. But that's been like the ultimate thing it's like as CEO, you're doing a great job.

[00:41:50] If, you know, in a jokingly way, like you've got nothing to do every day. I mean, there's so much to do, but if you're doing the job right, and you've kind of achieved the point where you have seven or eight direct reports in the C levels or VP levels, They're just going to go crush it and then, you know, it's working.

Omer Khan: [00:42:08] Yeah.

Vishal Sunak: [00:42:09] It's working. I mean, this has been such a valuable thing. Like being able to be like, you guys got it, you got it. I'll be here. I'll be here. If you need me. I probably don't bring them here if you need me.

Omer Khan: [00:42:19] But that's not always that easy to do, especially if you're the guy, you know who, it's your baby, you built the thing. It can be challenging to, to let go and step back.

Vishal Sunak: [00:42:30] It can, it takes a lot. It takes a lot of trust. And I'm so fortunate that my CTO and I worked at Backupify.  My co-founder Chris and I am a CRO Backupify, my CMO Backupify, my VP of Customer Success at InsightSquared with me. And I just know these folks.

[00:42:49] I just know them for so long and know we may have lost track of each other and kind of they've gone out in other ways, but I've seen them grow from when we were all kind of director level and manager level and see them grow into these amazing, amazing leaders and being able to say, I trust, I trust my CMO Juliet with our brand, our product marketing, our content, everything.

[00:43:13] Because she's an expert. She's an expert. I'm always there to help him what was there to send her ideas, but it's that trust. Right. And seeing the results and feeling like we all one together. Right. I have unified the whole company around that. Like when the ARR line goes up into the right it's every single person in this company helped, whether you're a QA engineer or a UX designer, or obviously you work in the sales team, you're the one closing these things, or you work in finance and you're, you never mess up payroll ever.

[00:43:46] You get everyone's commission calculation done perfectly paid on time and stuff like that. We're all responsible for it. Right. Every single one of us help outline grow. It's not, it's not just sales. You need a great product to do it. You need a great infrastructure. You need a great strategic thinking, competitive, competitive landscape.

[00:44:01] We're all working on it together. And, and you just go out and win, go out and win and have a lot of fun.

Omer Khan: [00:44:07] Yup. Love it. All right, let's wrap up. We're going to go into the lightning round. Can I ask you seven quickfire questions? Just try to answer them as quickly as you can. Ready? What's the best piece of business advice you've ever received?

Vishal Sunak: [00:44:20] Customers want to work with people they know, like, and trust.

Omer Khan: [00:44:23] What book would you recommend to our audience and why?

Vishal Sunak: [00:44:26] Predictable Revenue, Aaron Ross. It's the foundation of inside sales. If you're an inside sales kind of business book Starfish and the Spider got decentralized leadership I liked that book a lot.

Omer Khan: [00:44:38] Attribute or characteristic in your mind of a successful founder?

Vishal Sunak: [00:44:42] Grit, determination, right. Grit. Don't give up. Can't give up.

Omer Khan: [00:44:47] Yeah. What's your favorite personal productivity tool or habit?

Vishal Sunak: [00:44:52] I like to use Google Calendar in my personal life and, and block out things because I have the memory of like a sieve now running the company and being a dad also.

Omer Khan: [00:45:03] What's a new or crazy business idea you'd love to pursue if you had the extra time?

Vishal Sunak: [00:45:08] I'd love to get into engineering, infrastructure tech kind of a, like a snowflake computing fanboy, and also a software for like product managers. I, I, I think there's, I think there's a big market there.

Omer Khan: [00:45:20] Hmm. What's an interesting or fun fact about you that most people don't know?

Vishal Sunak: [00:45:26] Hmm, good one. I I can play three instruments piano, guitar and tenor saxophone.

Omer Khan: [00:45:31] Wow. Wow. I I've got a guitar. That's been sitting next to me for 10 years and I'm still trying to learn the second chord. So I guess some tips from you. And finally, what's one of your most important passions outside of your work?

Vishal Sunak: [00:45:42] Being a dad being a dad to a beautiful two-year-old little girl and being a husband too. And so spending time with my family and, and watching sports and hanging out grilling it definitely grilling. I love grilling.

Omer Khan: [00:45:58] Awesome. Yeah. It must have been a little hard with the Patriots, not even making the playoffs this year.

Vishal Sunak: [00:46:02] Yeah. You know, I've, I've gone through a series of emotions, but overall happy, overall, happy, happy for Tom. Happy for my buddy, Tom.

Omer Khan: [00:46:11] All right. If people want to find, find out more about LinkSquares, they can go to And if folks want to get in touch with you, what's the best way for them to do that?

Vishal Sunak: [00:46:22] I'm on Twitter. I'm on LinkedIn. You can surely email me the vishal[at]linksquares.[dot]com.

Omer Khan: [00:46:30] Awesome. We'll include a link to the to your Twitter and LinkedIn profiles in the show notes. Great. Well, Vishal, thank you so much for joining me. It's been, it's been fun chatting and kind of hearing the story of just how this, this this opportunity or this situation at backup, Backupify turned into a business idea and how you've grown that.

[00:46:51] So thanks for sharing the story and, and for you know, some of the lessons and things that you've learned along the way I appreciate that, that I wish you and the team all the best of success.

Vishal Sunak: [00:47:00] Thank you so much. I want to thank you for having me on.

Omer Khan: [00:47:02] My pleasure. Cheers.

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