Scaling a SaaS: Lessons from LinkSquares’ $40M ARR Growth – with Vishal Sunak [349]

Scaling a SaaS: Lessons from LinkSquares' $40M ARR Growth

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

I originally interviewed Vishal on episode 281 in early 2021 where he shared how LinkSquares went from an idea to a thriving SaaS company doing $10 million in ARR, raising $21 million, and growing to a team of 70 people.

Fast forward two years, LinkSquares has grown to around $40 million in ARR, raised $161 million – including a $100M Series C round in 2022 – and reached an $800M valuation. The company now employs over 400 people.

So it seemed like the perfect time to invite Vishal back to the podcast to unpack what's happened in the last 2 years to drive that growth.

In this episode, you'll learn:

  • How LinkSquares refined their Go-To-Market (GTM) approach to create a more predictable business.
  • How Vishal's increased focus on strong unit economics has not only driven growth but also helped the company withstand the current economic downturn
  • The challenges and lessons Vishal learned from recruiting, hiring, and onboarding more than 300 people in just two years
  • How Vishal's role has evolved from tackling every aspect of the business eight years ago to now leading a team of experts in their respective fields

It's an inspiring story of a SaaS business that started with a humble $25,000 check from Vishal's father and shows how the founders' early efforts, like spending nine months interviewing potential customers, have paid off, resulting in a solid and successful company.

I hope you enjoy it.


Click to view transcript
[00:00:00] Omer: Welcome to another episode of The SaaS Podcast. I'm your host, Omer Khan, and this is a 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 talked to Vishal Sunak, the co-founder and CEO of LinkSquares, a contract management solution that empowers in-house legal teams to draft store search, and analyze all their agreements.

I originally interviewed Vishal on episode 281 in early 2021, where he shared how LinkSquares went from an idea to a thriving SaaS company doing 10 million in ARR raising $21 million and growing to a team of 70 people. Fast forward two years, LinkSquares has grown to around 40 million in ARR raised $161 million, including a $100 million series C round in 2022 and reached an $800 million valuation.

The company now employs over 400. So, it seemed like the perfect time to invite Vishal back to the podcast to unpack what's happened in the last two years to drive that growth.

In this episode, you'll learn how LinkSquares refine their go-to-market approach to create a more predictable business. How Vishal increased focus on strong unit economics has not only driven growth, but also helped the company withstand the current economic downturn.

The challenges and lessons Vishal learn from recruiting, hiring and onboarding more than 300 people in just two years, and how Vishal's role has evolved from tackling every aspect of the business and building the MVP and talking to customers to now leading a team of experts in their respective fields.

It's an inspiring story of a SaaS business that started with a humble $25,000 check from Vishal's father and shows how the founder's early efforts like spending nine months interviewing potential customers, have paid off, resulting in a solid and successful business. So, I hope you enjoy it.

Vishal, welcome to the show.

[00:02:17] Vishal: Hey, Omer, how are you?

[00:02:19] Omer: I'm great. I should say welcome back. So, this is a follow up after two years, right? I think e episode 281. I wrote that down somewhere.

[00:02:27] Vishal: What are you on now?

[00:02:28] Omer: You're gonna be 350 I think, or something like that. So, chugging along slowly, so a lot has happened since we last spoke with LinkSquares.

Let's go through the usual stuff. So, tell me if you have a favorite quote, something that inspires or motivates you that you can share with. I can't remember what you said last time. So, you can reuse that. Nobody will ever know or give us a new one.

[00:02:49] Vishal: I'm a diehard Patriots fan in written outside Bill Belichick's office.

The coaches prove it every week, and I always think about that.

[00:02:56] Omer: Love it. Short and sweet. So, for people who aren't familiar, tell us about LinksSquares. What is the product do? Who's it for and what's the main problem you're helping to solve?

[00:03:07] Vishal: We are building software for in-house legal teams. We have amazing end to end contract management software. So, that's everything from creating new contracts and versioning them through red lines, getting them approved, getting them signed. We have made an e-signature and then an amazing repository to store your contracts at rest, and we invented a form of artificial intelligence that reads the contract and creates metadata summaries.

So, all in all end to end contract management from start to end and where you store it and all the kind of long tail obligations. And businesses buy LinkSquares because contracts are messy at every kind of stage, either when you're creating them or negotiating them. And certainly, when you're trying to understand what you've agreed to, and businesses use us to make more money, save money, identify areas to be more efficient and just work better overall.

[00:04:05] Omer: When we spoke last time, I think it was March 2021, LinkSquares was doing around $10 million in A RR. You had raised $21 million. And the team was about 70 people. Tell us how that's changed in the last two years. What is, where are you now?

[00:04:29] Vishal: Yeah. Team is 430 or so. We have a large presence in the Boston area, maybe 300 folks, and then over a hundred running in 20 different states.

Mostly engineering supportive engineer. So, that's been wild. The company is very big now. We can't even fit in one room together unless it's like a giant ballroom that would host some, 500 person wedding reception, . That's been really awesome. And we raised an additional $140 million.

So, we did a $40 million round in 2021. That was our series B, and then we raised a $100 million last year. Our series C and the company is doing extremely well.

[00:05:13] Omer: So, ballpark, where are you in ARR?

[00:05:15] Vishal: Now? We are like, around 40 mil of ARR right now.

[00:05:19] Omer: Awesome. That is quite a journey that you've taken over the last two years and there's a lot of stuff for us to unpack there.

Before we get into that, I want to just give people who are listening to this who may have not heard the last episode, and I would recommend people go and listen to that. We went into a lot of detail about how you came up with the idea and how you guys basically went from zero to $10 million in ARR.

So, I wanna do a condensed version of that just to give people a taste of what we talked about. So, what, can you just tell us, like where did the idea for LinkSquares come from?

[00:05:57] Vishal: I was working at a tech company with my co-founder and lots of folks on my management team and lots of folks in the company now.

We were a small private company, maybe a hundred people and a much bigger company, like a multi hundred person company came in and acquired the company. And during that acquisition they asked us what was in contracts we had signed with our customers. They had lots of questions and wanted to do things anticipatory for the acquisition being closed.

And the answers to these questions were really hard. We had large volumes of customer contracts, A lot had been negotiated, lots of third party paper. And so it was a real light bulb moment for us struggling to get these answers for the acquirer that came in and bought the company and light bulb to be like we're not so like different.

We're a series B venture backed company with massive high growth. Why is this the way that it is? And that's what got really got the company.

[00:06:52] Omer: So, that was back in 2015. What did you guys do to get started? I remember we talked about this Rubion Rails app that you built, which was basically a front end, didn't actually do anything in the back end, but you were using that to go out and show customers, and I think you spent around nine months just interviewing.

Potential customers before you started actually moving forward?

[00:07:21] Vishal: Yeah, that's right. Ultimately, our end buyer ended up becoming the general council and enough smart people in the Boston scene that we're a part of, nudged us towards the thought that the general council at companies has this under their purview contracts and managing contracts and what's in them.

But we didn't know any general councils. My co-founder and I are not lawyers, just like startup people and startup operators. So, we did the only sensible thing, which was to buy 30,000 emails that someone, I think it may be Pakistan, mind them off LinkedIn. Amazing source of leads that we had. And we did the only other logical thing, which was to cold email them and say, my name is Vishal and I think you have this problem.

Cuz I work at a company that is just like yours. I used to work at a company just like yours. And that's how we got started. And we started getting feedback and putting the business problem and the business pain that we had right next to the person that could have. Without the presence of a fully baked product made a huge difference.

And to what you had mentioned when we talked about in 2021, was just having the ability to do like applicable prototype that has like a low bar in terms of cost, but you can iterate rapidly and show people what you're thinking about. What a joy it is in 2023 that there are so many amazing products that can help with like prototyping like that, including Figma and Envision and other tools.

And so as we got started back then, those were in their infancy or didn't exist, and we just did a basic Rails app without any backend or any kind of controller actions that actually wrote data. To the database, but it was just serving and refreshing the same fake data over and over again. And that was massively helpful.

We got a lot of feedback that way.

[00:09:19] Omer: I'm curious about the cold emails that you sent. Lots of founders will do something similar and they'll start cold emailing prospective customers and it's crickets. And not only were you doing the same thing, but you are targeting general councils, right?

This is not an entry level attorney in a company or something. What do you think you were saying in those emails that was getting these senior people to pay attention and, many of them actually respond to your cold email.

[00:09:53] Vishal: We had a built-in advantage that no one emails the general counsel for anything good.

Or it's just like law firms trying to email them to be like maybe your outside council of choice or whatever. And so given that our buyer isn't susceptible to the same amount of cold email that says like CMO gets or a CRO or VP of Sales has, they were very receptive to that as a channel and would often reply either through their professional obligation to.

Create a stance either way for the company, and a lot of people raise their hands and said, this sounds really interesting. Let's talk about it.

[00:10:34] Omer: And you spent about nine months interviewing these people. I remember at the time you saying that you were worried about building the wrong product and wasting money and, really making sure that you had honed in on the right problem was really important to you.

Why did it take nine months? For you to get there. Do you feel in hindsight you could have got to the same conclusions earlier? Or was it just this kind of, iterative process that just took that time to really uncover what the deep underlying issues were that needed to be solved?

[00:11:09] Vishal: You want to have statistical significance I'm a data guy, I'm a op guy, like building software. And to get statistical significance. That answer can't be, I talked to 10 people and I'm ready to quit my job and go full-time and forsake all my other opportunities, and you can't do that after 10, probably not after 20.

So, we set the internal number at a hundred and got into maybe 70 or 80 types of completed conversations, or they were good interactions. Also, when you. So, early and there's really not much else other than will you take a basic call with me and I can learn that actually happens slower. Just on a conversion rate basis, if we send a thousand emails, there'll be a large portion that don't respond or tell us to go away nicely or not nicely.

And then what comes left? What's left for us is then opportunity to learn and. We didn't wanna feel rushed and certainly didn't wanna build anything that no one wanted. Cause that's like a quick way to fail, a guaranteed way to fail. And we just took our time until we got to about 70, 80.

Could we have gone to the aspirational 100? Sure, we could have, but there was so much kind of vibrancy and energy around the idea that it made sense to us to start actually building the thing from.

[00:12:33] Omer: Had you raised any money at that point or were you guys bootstrapping in those early days? In that first year or so.

[00:12:40] Vishal: Bootstrapping my dad wrote us the first check, 25 grand.

We got a grant from Northeastern University, my alma mater that has a wonderful entrepreneurship program. They gave us $9,000. So, I think that's all we had back then. We had a war chest of $34,000 to play around with, and not much more other than that. As the founder journey is hard and it's not always like we were always 3 million bucks and we have a PowerPoint and a bunch of ideas.

What a luxury that could have been back then, but the struggles of the early days and the kind of painstaking customer development ended up net netting. You like something that can catch fire, which is exactly what happened in LinkSquares.

[00:13:23] Omer: So, after the nine months or so of doing these interviews with general counsels and you guys get to the point where you're like, okay, now we, maybe you have that statistical significance you feel.

That you understand the problem and what solution you need to go and build at that time. In that first year, how big did you think the opportunity was? Like even if you didn't say it out to people, like where did you hope the business could get to In terms of sites?

[00:13:57] Vishal: Yeah. With our buyer and just our technology and what we do with contract management, like the TAM is like infinite.

The addressable market is like, It's every single company in the world has contracts to do whatever. I don't care what your business model is, you have contracts. And it felt like if we could keep going, keep learning, get the product right, get it out the door, we would have essentially every company in the entire world in our disposal, should we choose to go after it.

And that brought a lot of energy to the business because one bad call didn't. That it was over, it just meant we'll just go find the next best good call to have. And that's so how we feel about it. And there's just so much opportunity just with our market and existing technologies. And why haven't lots of legal teams bought software and there's a internal revolution that we had no idea what's happening in the back.

Until we started going to like industry trade shows and hearing general councils talk to each other about how they're trying to shed an old identity of being like Dr. No. And say, and just managing risk. And they themselves, were going through like a transformation, generational transformation. I think with much younger general counsels coming in too as baby boomers set off for retirement.

And the new general councils like pretty cool. Like they use Slack and they like technology. They work on Google Docs and sheets. They were ready for something and part of their own revolution, which we're so happy to be a part of, which was they're trying to rebrand who they are and they want to be the CEO's BFF and be the person the CEO call CEO calls to say, we got a tough business problem.

We don't have a tough legal problem. We just have a tough business problem, and who do I want to be around the table when we try to go solve it? And that, and. Credit to our buyer. They're the ones who have been pushing. We wanna just be different. And the other fact is like all their peers on the executive team just wipe the floor with them with data that they have.

Marketers at large companies have access to unbelievable amounts of data, SEO data, lead gen data, pipeline data source data ROI data, marketing attribution, all over the place, content marketing, whatever it is. Same with revenue teams. Every year another of groundbreaking revenue generating or supporting product will come out and they.

Use it all the time. They use what's cutting edge and legal really hasn't had the opportunity to use what's cutting edge. It's just a beautiful kind of symphony of things that occurred. And I think for people listening out there, some of this stuff you can predict, but how much time could you actually spend trying to say legal is going through a cultural revolution and we're gonna be a part of it.

It's like we didn't even know that was happening when we started the company. We figured that out years and years later. You just get in there and see it through and don't give up. Those are the reasons why great companies get Bill. You just don't give up. Great. So,

[00:17:08] Omer: I think that's a good recap of what we covered in the last interview.

I would strongly recommend that, if you want to hear more of the story in terms of zero to 10 million ARR, go and listen to episode 281, Vishal goes into even more details on, on, what he and his co-founders did. So, let's pick up from there. I wanna unpack what's happened in the last two years.

That's 4x your A RR helped you raise, 1$40 million and, a ridiculous increase in headcount from 70 people to 400 plus. What do you think have been the growth drivers? What's, what are the things that have given you that, that kind of spike in growth over the last two years?

[00:17:53] Vishal: Yeah. Past 10 million ARR you've firstly done something that's probably point, 0.4, 0.5% chance of all companies that have ever done it, to have this business model. And once you're like past that stage, you don't fear the reaper as much. , you should fear the Reaper all the time, and there's certainly many good reasons.

Silicon Valley Bank and the macroeconomic environment and VC sentiment changing. There's certainly lots of things to fear the reaper, but if you have a decent balance sheet of cash, you know what you did to get to 10 million arr, and so we really focused on like predictability and go to market, a massive investment in like data collection and then building more of a rigor around like what data do we look at and how do we use it to guide decision making.

You turn from like we're a getting lucky type of company, probably like a millionaire, two millionaire. We're like so lucky. Like I used to tell my wife like, every deal, we close. And then she would be like, okay, why don't we just set like above a certain threshold because you're now just doing so many every day and every week.

And now I just don't tell her about it at all. She's like, how's a quarter going? And I'm like, I gotta deal with this at home too. , that's funny. Go to market. Predictability, lots of data. Understanding go-to-market predictability at a really deep level as like me, my CRO, my CFO, and understanding that has been really key.

Like, how do we triple the revenue next year? Let's get started on it a year in advance, and let's just think about it. Let's just dream about it. How will we do it? How many reps do we need? How many leads do they need? How much pipeline do they have to make? How many demos do we have to do? You get more mature in building like a more accurate funnel that you can lean on for like predictions.

And so ultimately that's something you just build up over time. It's go to market predictability for sure. And then like sticking with channels that are definitely working, like there are certain channels that are just very good for us and we keep on doing those over and over.

And then starting to experiment kind of 20% of the marketing budget with kind of other channels that we only thought of, but it really maybe never had the cashflow to go and do it. So, that was great. That's how we did it. Don't bet the farm on anything new. Continue to build, go to market predictability and the whole funnel end to end, and then go out and just do it.

Run the play this quarter.

[00:20:25] Omer: So, let's talk about the go-to-market motion and where it. Two years ago to where it is today. Part of that is as you said, like setting the the vision of where you want to be and what are all the pieces you need in place to be able to get there.

What else did you need to do in order to get that predictability? For example, one of the things that struck me, When you talk about a, an total addressable market, which you said, potentially is infinite, there's upside to that. But the downside also is it's so horizontal. Like where do you focus and how do you make sure you're messaging lands in the right place, whether it's by vertical or whatever.

And so when you talk about your GTM and predictability there, can you give us a couple of examples of specifically some things that you changed that. Drive that predictability.

[00:21:15] Vishal: Every customer that we would bring on, we would go and get a very accurate industry company size range, number of employees, and go and scrub it.

Scrub Salesforce, regardless of where we got it from initially. So, all of these accounts were like self-prospected or it came through like a data source, like ZoomInfo, but just make sure that we have a predictable set of data that we can get industry, company sized number of employees right now, and then pivot it and look at it.

You can't look at it every month because it's too erratic. It could be too erratic. , but then look at it on a quarter and say like, where are we having success? What verticals are we doing really great in? Are we doing really great in construction companies? Then go and then layer on those with how many offs did we generate?

How many were closed? One, how many were closed off? How many are still in the buying process? What? What's the a p on those deals? What's the pipeline that we created out of construction companies? Or pick a random, a food and beverage or whatever. and then ask ourselves like what channels what industries are potentially maybe bad fits right now for whatever reason.

and let's stop wasting time doing artificial demonstrations for people that will buy like, and some of the data will be very cut and dry, like you've tried 24 times to sell to this type of company and this industry and this company size. And the fact is whatever it is, they don't want it . And so maybe we can just cool off on spending our sales reps.

Like in a channel that has never had one transaction been done in, or an industry or a company size and just go to market refining, you're making like little course corrections on the boat as you're driving in on the ocean, you're not like, engine full. Trying to do like a right hand rudder turn on the giant oil tanker.

It's like we're just like navigating through waypoints and using. That was like the biggest thing. It's just getting clean and reliable data because I'm telling you, when you've wrapped up 200, 300, 400 logos and you haven't gone back and scrubbed it, and then all of a sudden you need all this data, like those are your nights and your weekends and I'm the one that had used to do it back in the day and I had a job like this in revenue ops, so I know the value of it.

So, we just started investing in it immediate. And it doesn't take a lot of effort if it's just happening every day that a new logo gets created and then you're building in the rigor to go and review it. And then we're review reviewing it as an executive team and we're reviewing it as like a broader leadership team with our VPs as well.

And then we're reviewing it with the board because we know what we're doing. And that's ultimately the magic. Like how do you keep on making it predictable is understand what's working, double down on what's working and. So,metimes, like some industries we just haven't had statistical significance talking to.

But maybe we've closed two out of six opportunities we had. Maybe we prioritize seeing if that turns into whatever it is, like eight, eight out of 48 or eight out of 40 or 10 out of 50 or whatever it is. And then we create. Target industry type of buyers that we want to explore so that we either know this could be a great channel or not.

And we found some great channels just being more introspective. I say channel, but I really mean industries and company size mixes. But then you can devote dedicated teams to say, there's enough pipeline here, and it's closing at 50%. So, just do as many demos as we possibly can. And we know that half of them will buy.

And then you start like running your go-to-market like very much more tactically. And yeah, we can't talk to every company in the world, but then it's okay, we have a hypothesis about EMEA. Okay, great, how do we get started? Let's fly over to London and go do some industry conferences and go and check out the local scene and sponsor a booth and spend some time there just understanding is this a good market for us or.

Are people receptive to what we're saying? They're certainly receptive in Amer America and Canada. But what about London? And you just kinda go from there. That's really been a key.

[00:25:28] Omer: The other thing you mentioned was in, in terms of growth drivers was just having a focus on strong unit economics.

Can you explain a little bit of what that means to.

[00:25:41] Vishal: Absolutely. One of the keys to the late stage fundraisers, after you get past the a and you're past 10 million ARR is largely just all driven on unit economics and tam. Those, that 40 million round, a lot of it had to do with go to market efficiency and scaling.

Again, all the things we had invested in already the hundred million round, we did Series C, a lot of it. We are in control of our unit economics. We are not victims of our like gross margin without any ability to know how to control our cogs or whatever. And so a lot of my job now with my CFO and my finance team is, and my ops team is just building so much more sophistication on forecasting.

All the unit economics will be like two years from now. Can we forecast what our cost of goods sold is for an entire year? We can. We never had that back in the day. We've also been building all this infrastructure inside the company to just, again, make better predictions and be in control of the unit economics and know what the best in class is for every unit economic across the board.

Then go and do those, make those, turn that forecast into ours. That's the hardest part when you're commanding a larger army like I am, is so much of the business is just like I'm doing my thing. I'm building software, I'm taking care of customers, I'm doing implementation, I'm doing support, I'm doing marketing.

But the executives really have to look past all that. It's what is the business overall like? How is it running? How is it running? And are we doing a great job based on whatever information we know about the world today and what best performing companies look like? and then just going out and executing it and that's really been what we've been doing now.

It sounds easier than it is in real life and have plenty of gray hair. I think from the last time I talked to you. I have another kid also, so you know, we have two beautiful girls now, but that's certainly driving it. The gray hair as well. And you just get better at just thinking about unit economics into every decision you make.

And that's ultimately like how you grow up as a leader of a company is how well do you know unit economics, CAC, payback, burn, multiple gross margin, ARR, productivity. And then can you control them, and can you get them to the, what you want them to be?

[00:28:04] Omer: In terms of hiring, in the last two years, you went from.

70 people to over 400. So, people might hear that and say, wow, lucky Vishal, he just got all this money to hire all these people. Great. But there's also a lot of pains and headaches and challenges that come with hiring that many people and that quickly, can you tell us about your experience of that?

Like what have been some of the challenging aspects of being able to. The right people, you know at that scale so quickly.

[00:28:40] Vishal: It's a big-time commitment regardless of how ambitious you are on trying to hire people. It's a big-time commitment to run a whole interview funnel. Diverse set of candidates they each get talked to initially and then they, some of them get interviewed and.

Just the time you have to spend, it eats away from everyone's day job. And if you're trying to do something massive, like we're gonna double the size of our sales team like it, it ends up being like a operational kind of gopher hitting like arcade game. And that's really hard. That's just really hard to do.

We had to have a huge talent acquisition team to help us and. There's just, candidates that you just have to keep filling up in the funnel and we're so fortunate. We hired some amazing talent acquisition experts that came in and are truly the best at what they do of finding great candidates to hire.

Then it's like the onboarding is very challenging. If you're not at the point where it's almost systematized, like YouTube level, I can just watch stuff about the business and learn. If you're still like writing things on whiteboards, trying to train people by hand, it'll never work at the volume.

We've always invested in doing really great training in the company, and there's specific training for each department and then there's we call executive level training where every executive in the company will spend some amount of time with every person that gets hired.

So, first they get to know us and be, they get to know how we think and what's important to us. Yeah. And then the other thing is just building up the entire infrastructure around what I call being a best place to work. And being a best place to work is like fair and equitable pay upfront career laddering, like I'm a senior engineer, how do I become a senior engineer too, or a principal, or I want to be an individual contributor versus being on a management track where I'm trying to manage people of the same.

Having career like banding and laddering and promotion paths, and then the performance review cycles and committing to doing it regardless of how painful it is to give everyone in the company two times a year, a performance review sometime in June and sometime at the end of the year as well. And that just, that takes a.

That takes a lot. And even having a large balance sheet worth of cash can't make it better because you have to build stuff. You have to build processes, you have to write core documents around, what are the laddering all the way up from, you're an intern to your senior vice president in the company.

And that just takes time. And to do it right is to treat your employees the best you could possibly treat them. Everyone has a fair job description. No job is completely ambiguous. They know what they're gonna do every day. They know what expectations there are. They know what goals they have for this year, for the department, for the company.

Communicating all of that is more than a full-time job. It's the full-time job of inside Lincor, maybe more than 10 people, 12 people, 15 people just dedicated to this whole people function. It doesn't work without people. And then how do you become a best place to work? Now you're a preferred employer over some other massive giant company that's even more famous than us, but people still wanna join.

So, it's like all these things, there's no silver bullet when managing human beings and doing it well. You just have to do the work. And that takes a long time.

[00:32:04] Omer: I think eight years ago you were the guy doing the interviews, you were the guy figuring out how to build the MVP and, make that work.

Basically, doing everything along with your co-founders. When we spoke a couple of years ago, obviously that had changed. You had hired a bunch of people, the company had grown, hit the $10 million ARR milestone, and then even now, when I hear. Talk, I can see and hear the transition that you've made yet again in the last couple of years as a CEO and a leader, how do you, how has your job changed in the last couple of years?

[00:32:50] Vishal: In a really rudimentary sense, anything I used to do a couple years ago, we hired expert to go run, like great example. Security questionnaires are a big part of probably every SaaS company at this point. And in order to get these big companies on board and using the platform, part of the deal process is doing security questionnaires.

I've done hundreds and hundreds of security questionnaires and sometimes I've done seven or eight on the last day of a quarter, like in my desk, a machine, because that was my job. That was one of my 50 jobs I used to do. And when we raised the hundred million dollars, It was like, what? How do I wanna spend my time now?

I still love to do it. If they needed me, I would jump in. If this whole team had, the stomach flew at the end of the quarter and couldn't do it, I would do it. My CTO would do it. Cause we, that's just who we are. We've just been doing them forever. That's a good example of something like I gave away.

Now you don't realize that, that you become so good at doing something over and over again. Everyone lies on. Everyone on the sales team relied on me to do the questionnaires, relied on Eric, our CTO, do the questionnaires. Now you gotta build trust with another team. And maybe it's not the same transition between the, the co-founders of the company or yeah, Eric I think of like my co-founder too, but like you're getting a certain level of service from the people that have essentially grown the company from nothing.

Then you're transitioning and you put a lot of trust in them. Again, there's no silver bullet. We had to train them on how to do all this stuff and luckily we hired some great experts that knew a lot, but there's still nuances about how we work. And so that, that's like a big thing. My job was to hire sixth grade executives and I did someone to run marketing, finance, legal, revenue, products, technology, and then my job is to tell them what's important this quarter, this year, this month.

Mostly just get out of the way now and never go down into my executive teams how they do it. I'm not a master marketer, I'm not a master revenue expert. I'm not a master developer. I'm not a master of really anything or an expert in any way. But I know enough about a lot of things that we can have an intellectual conversation about, something they're stuck on.

My job is not the how anymore. I only focus on what… I never really tell people who work for me directly like how to do it. So, that's like a good change. I used to be a doer. I used to be part of the strategy of the security team and how we used to help our revenue team. I don't do that anymore.

That's a good example. I don't run the deal desk anymore, but I loved it. I did it for hundreds and hundreds of deals. I love it. I would still do it every day if they would let me, but they won't let me anymore. I in a good. and so you like figure out that I'm mostly in charge of the future now.

If everyone in the company has something to do that is related to this quarter, this month, then who is just like staring figuratively, staring out the window thinking about the future? That's me. Am I? Am I like my CFO also? And we're just like thinking about okay, like how long is the cash gonna last?

And if we can keep performing at this level, like when was the next time we need to raise capital and how much do we need to raise? And then I do a lot of just kind of investor relations with our existing investors. And then I do a lot of investor relations with kind of potentially new investors, just doing tons of introductory calls every single week.

I do them all the time. They reach out to me and we schedule a call and meet them at, tech conferences and we catch up. Some of them have known me for a long time and the job just changes to I have nothing to do, which people may chuckle about. I could do lots of things. I'm happy to do anything, and that's really my stance.

If you need me to do something, I won't do it. You need me on a closing call. I'm there. You need me to help with a order form. I'll still help. But I really don't need to do it anymore because of the scale of the company. And that's great because now I can really think about what comes next product vision.

Where are we trying to go? Where's the company gonna be two years from now? Already now when we're like, I'm already onto 2024. Like I, I don't, I know what's going on right now. This is something we dreamed up last year. We're just running the play like a quarterback right off the wrist. We're gonna run, do this, draw, play right, and then we're gonna throw a long bond and we already know what we're gonna do this quarter in terms of execution, that we just have to go out and do it.

I live in the future now. Future boy.

[00:37:25] Omer: Future boy. Love it. Before we started recording you said to me that these days you feel like you're managing four different companies. Yeah. Can you explain that a little bit for our listeners?

[00:37:37] Vishal: Yeah. Over the years doing the job, you see what it is. and you're not running one company LinkSquares.

I'm actually running four companies that have all different needs all at the same time, which makes the job really hard. So, the first company I run is like a company full of people, which we talked about a best place to work and fair and equitable pay, and a career ladder and a promotion path, and a great job description and just goodness of how we help the community and charities that we support as a business.

And just we're out there in the world with a bunch of humans. Are you proud to work at Link Squares and do you love the experience you're getting? The second one is just all spreadsheets, financial spreadsheets, SaaS, unit, economics, the whole thing, just all spreadsheets all day long. And then it's a company that has a brand that people who wanna join the company will examine.

Is this a great place for me? Part of that is also dev diversity, equity and inclusion, which is a huge part of how employees will now evaluate their future employers. And then the fourth thing is we are all owners in the company. Every single employee is an owner in the company and like it's an asset for ourselves.

And it's an asset for a whole bunch of investors and a whole bunch of LPs who gave money to our investors or our venture capitalists because they built it on the back of growing the value of the asset. And so, things will happen throughout the course of a year where let's say we go and we. 500 million series D it will feel awesome, right?

And that will benefit all four of the companies. It'll all go to the positive benefits of this happening. But then you look at companies that are like experiencing like large amounts of riffs and layoffs and why are they doing that? And if a decision of business has to make against the four categories, it's like they're trying to make their spreadsheets and their financial metrics like look better, cuz it may be inefficient.

and they're trying to save the asset value of their company, but it's gonna hurt, potentially hurt the people who work there. It definitely will hurt the people who work there if you're doing a large riff and it could, he hurt your brain. And so, it's like a really interesting framework that I think about now, if you have one of those four things are gonna be in the negative impact.

It's a very large, massive. If you have two or more, it might be the biggest decision you ever make in the history of the company, ever. And luckily, I've never had to make a decision that has two involved. But certainly, it makes you realize that these are all like interwoven together, but they serve all different purposes.

And some of them are conjoined and some of them are. And I've found it to be a really helpful frame framework to think about when I have to make a decision, what's it gonna do for the future? Why am I making it big decisions? That's the other thing about the job Omer, all the little decisions like low impact or medium impact.

We hired a bunch of subject matter experts that just can't make them, so I am only left to it. The ones that are too big for the filter to catch they're the ones that have the highest criticality, the most potential impact, the least potential amount of knowledge about whether it will go right or wrong, and someone has to decide.

And that is also a part of the new job. I only get the hardest problems to solve. And it's great cause I've been running the business from day zero and I know a lot about it, but that's also how the job changes. You hire a bunch of experts, and they go and they make all the easy decisions because you pay them to make the easy decisions and you trust them to make the easy decisions.

The big decisions still go back to the guys that founded it and me and that's just how it is. I wanna move on to the lightning round and wrap up here. One more question before we do that. You raised a hundred million I guess about a year ago which was probably a good time in hindsight, how have things changed recently with the economic downturn in terms of the way you are spending that money and the way you're operating the business?

We, as a company have always sought to run the business, with capital efficiency. We were never in a category of a company that was like growth at all costs. And so that wasn't even something we had to unwind in our thinking. We had never thought about that mostly cuz if you're like a first-time founder and no one knows you and you raised a bunch of capital, like it's special.

You wanna make it last. You wanna make it worthwhile. You want to reach your hit, your next milestones, you wanna get another. It's been very much like we've earned the right to have it. And I think there are probably a lot of listeners out there that probably think the same way if they have that opportunity.

It's like something that I don't wanna ruin because I was reckless with something that I needed. And yeah the macro economy is hurt everyone in the world the same way and it's harder to sell software, really hard to sell anything to anyone these days, especially businesses. So, again, having good predictability on go to market means that when July of 2022 occurred and all the things that happened when the stock market's dropping a thousand points every week, like our models need to be updated because the new kind of old model worked for a better economy and the new model, we have to rebuild it.

And then you don't have a lot of statistical significance that are flying blind for a little while. Like September or October, things get really changed in the world, and then you're kinda waiting to see whether you can make, many different flavors of modeling as to how you may end up.

It's just harder to raise capital now, so spending it fast doesn't make a whole lot of sense anymore. It used to be easier back in the day, you could light it all on fire if you want, or a giant party like HBO, Silicon Valley, Bach Mane Insanity, and. It's really taught us that you can't build a business that has too much sentiment on things you can't control.

If your entire business is predicated on venture capital sentiment, then it's gonna be pretty hard forever because it's not predictable in that way. And build a real business. Build a real business that delivers some value to some buyer who needs what you do every day, regardless of what that. And focus on like how can we create a business that is very real, that even with cash burning, do you understand that there could be an inflection point where you could be profitable if you wanted to?

And we understand that really well. So, then know why you're burning the cash. If you're burning the cash just to burn the cash, that's a terrible thing to do. Don't do that. But if you're burning the cash, cuz you're saying to yourself, we still have an amazing opportunity. We want to get a lot of market.

then it's like growth at reasonable costs. It's not growth at any cost. And then we as operators and other operators have to look at things like capital efficiency and burn. Multiple, which is how much burn do you have in a month? How much are you burning off? And then how much a r are you creating?

And that was something that became a lot more important, even though it was always important. Omer, it just became the thing everyone talk, talk about.

[00:45:02] Omer: Great. And on that note, let's let's wrap up. Gonna get onto the lightning round. You know the drill. You've done this before. I'm just gonna ask you seven quick-fire questions.

Are you ready? What's one of the best pieces of business advice you've ever received?

[00:45:15] Vishal: With humans, the first 30 days, like the next 3000 and that's just how it goes and so make quick decisions if the first 30 days are not going the way that you want.

[00:45:26] Omer: What book would you recommend to our audience and why?

[00:45:28] Vishal: For sure, Predictable Revenue, even if you're not in a sales role, but maybe you're a founder of a company. Just understanding how inside sales works and how it was created. It's obviously changed a lot over the years, but that has still the foundation of how most inside sales teams.

[00:45:42] Omer: work. What's one attribute or characteristic in your mind of a successful founder?

[00:45:47] Vishal: Grit. What's your favorite personal productivity tool or habit? I like, I like Notion I keep my life organized in notion in either in cards or individual notes, and. It's a pretty slick little product. Definitely getting better for sure. But I really love Notion.

[00:46:03] Omer: What's the new or crazy business idea you'd love to pursue if you had the extra time?

[00:46:08] Vishal: I think the only thing we have left for AI, generative AI is just like generative AI music. Write me a ballad and John Mayer style and record it for me and give it to me and I think I'm excited. Generative music AI one day. Cause I'm a big musician and a big fan of music.

[00:46:24] Omer: So, what's an interesting or fun fact about you that most people don't know?

[00:46:27] Vishal: I was born in Brazil. My parents were living there, we're Indian, but my parents were living there. We moved to America when we were, when I was one in 1985. Another fun fact you can read about me but harder to find is my first cousin is Prime Minister of the United Kingdom. My dad's brother's son, we share the same last name.

[00:46:45] Omer: Oh, that's right. Yeah. I never made the connection, but yeah. Finally, what's one of your most important passions outside of your work?

[00:46:51] Vishal: I'm a dad of two beautiful kids, two beautiful girls, four and one, and that, that takes a lot of my time up. But I play guitar every day and I've been doing it for years now, and I love it.

And I love playing guitar.

[00:47:03] Omer: Thank you so much for joining me, coming back and updating us on the LinkSquares. Just digesting what you have done and gone through over the last two years is pretty mind-blowing. I think you were at what a $800 million evaluation, when you raised that last series C round, would would love to cash up again in the coming years and see where you continue to take this business.

If people wanna find out more about LinkSquares, they can go to and if folks wanna get in touch with you, what's the best way for them to do that?

[00:47:33] Vishal: Oh, connect with me on LinkedIn. I'm on there every day.

[00:47:35] Omer: Great. We'll include a link to your LinkedIn profile of the show notes. Vishal, thanks again.

Wish you and the team the best of success. It's been a pleasure catching up. Congratulations on all the success to date and I wish you and the team the best of success in the coming years.

[00:47:49] Vishal: Yeah, I'll see you in a couple of years. I'll another update. We tripled the size of the company. That was my dream.

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