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EP 8: Sasanka Atapattu, Founder & CEO at LaunchSource

Podcast Transcript

James Mackey  0:12  

Hello and welcome to Scale by Design. Today we're joined by Sasanka, the founder and CEO of LaunchSource. Sasanka, welcome to the show.


Sasanka Atapattu  0:20  

Hey, man, how's it going? Sasanka Atapattu, I am the founder and CEO of LaunchSource. It is founded in Boston. Now we're in the remote world, we're all over the place nationally. LaunchSource is quickly growing and becoming the number one GTM hiring marketplace to build and scale the most diverse sales team. So we're certainly solving a big problem in tech. But it's a problem that we see in a lot of industries. 


My background, as you know, and several others. I've spent the last close to 20 years in sales strategy and consulting, in industries like Big Pharma, market research, and now tech, which makes me feel a little bit younger. But yes, I have close to 20 years of experience. 


Passions of mine? Well, James, you've been out with me. So you know, I love food and drinks. Good, good. Good times. But I am a dad. I've got two beautiful daughters, some five, and a little boy, Bodie Hart Atapattu. And I love being around water in the summer. So I was fortunate to be up in Maine, this summer, hanging out on the beach, but also on the lake. 


And these days, I'm reading, reading to be a better CEO, being a better leader. And learning, you know, as we go, and an interesting time in the world, right, with the great attrition, with wars, with tensions in our country. But, you know, still, I think there's a lot of cool stuff happening. Both, you know, opportunities in the world. But you know, what we're here to talk about, like startups and stuff we talk about here and offline.


James Mackey  2:13  

For sure. And you know, before we hit record, like one of the things we said we wanted to talk about was just like high-level recruiting cycles, like what we're seeing right now in the market.


I want to riff back and forth, right, like, I want to share with you kind of what I'm seeing and what's happening and curious to get your thoughts on what's happening in the market right now, specifically, as it pertains to talent acquisition. 


What are you seeing out there? What trends are you seeing? And what do you think, what do you what are you kind of expecting to happen over the next three to six months?


Sasanka Atapattu  2:45  

Yeah, I mean, so again, just to set the context, the segment that I'm most familiar with right now, and that we work with is tech on both startups, pre, you know, I would say pre-series A up to IPO. And, we see both growths, and we see both consolidation or cuts or cost cutting.


And I think, in some cases, we see companies cut where they're, obviously over capitalized where we have seen a lot of hiring in the past. And this is where companies are taking a more disciplined approach. And I think the markets and oh my God, what's happening, but it's more discipline. Now I come from, as I mentioned, a different industry form, where we were very used to this and immune to a little bit more discipline. I think, in other instances, you see larger companies that are laying off, and it's more disciplined in terms of cutting those costs.


And so from a recruiting standpoint, people are still hiring. I think what we're seeing, at least from our standpoint, we're on the GTM side, and specifically in entry and early career sales and volume hiring, we're seeing more applicants, more flooded and we're seeing TA and recruiters be more stressed in that process. And inundated with a lot more applicants. And we're seeing business units, not just in sales, although that's our core expertise. But you know, I was talking to a talent lead and Amazon and he's facing the same problems in engineering and our for our, you know, recruiting recruiters, so we're seeing that piece there. 


So I think it's going to have a bigger effect over the three, three to six months in terms of hiring great talent. I do think the layoffs are going to continue throughout the rest of the year. Which means that you know, you know, we're going to have to rethink from talent acquisition and recruiting side, you know how to be more efficient? And then from a candidate's perspective, how to be ready and prepared, right? You know, for anything, both internal mobility, but also if, if it's your time, or there's a shift in your organization, you know, what are you gonna do?


James Mackey  5:18  

For sure, for sure. And what you said is very interesting that you think layoffs are going to continue for the rest of the year. So I have a similar kind of philosophy or thought process running what's happening right now, I think. 


And I think I've heard this too, on Wall Street Journal, stuff like that, that this is, you know, it's kind of like a slower contraction, right? And we don't know where the bottom is yet. But I am pretty confident it's not going to be anywhere near what it was in 2020. And so but it's just taking a little bit longer, like in COVID times, right? It was like two weeks, like boom, 90% of demand plummeted. Right. It was pretty nuts. 


And then within like three to six months, we were already rebounding. I think this is going to be slower, right, it's like taking longer for the correction to kind of kick in. And I think it's going to take a little bit longer to come out of it as well. So I think that it's kind of likely I don't know exactly the timeline. Like my perspective, I don't know if you're still going to be carrying for the next three months, six months, but you know, it's kind of nice about it, I guess it's like there's time to react. Right? 


Like we have time to be strategic about how this is impacting our businesses versus COVID. We're just like, WTF like, this just happened so fast. And now we just have to do a complete overhaul on everything to get, you know, to get through to the other end of this right. 


Sasanka Atapattu  6:44  

Well, yeah, but to be clear. So this is important to think about. When I say layoffs are going to continue to happen. Maybe I need to rephrase, that restructuring of organizations is going to continue to happen. 


So what that means is, that companies are rethinking about, do I need this department and seven different functions. Right, so that they may reinvest in other organs in other parts of the organization. Right. So what we're seeing in our own business is, hey, they laid off STRS in one department, but they're still utilizing our platform in another area. Right. So that's interesting, right? And they're speaking to us about their hiring plans in q4, and q1 of next year, right? 


So because the cost grades are there. So I think when you think about it, from a candidate perspective, you've got to think about, hey, you know, if you're an early career individual, do I have the skills? Or am I thinking the right way about my career? If you're in a company, you know, am I efficient? Do I have the resources if I'm in my head of talent, you know, am I adaptable? For this change? Right? 


So companies are still going to hire to be clear, but it is going to change. Meaning even in my organization, my planning, and what I was going to hire for q3, and q4 is different now than it was two months ago.


James Mackey  8:29  

For sure, for sure. And I think, quite honestly, I think people in our industry are the ones who seem to be the standard benefit from a lot of market volatility, like I'm very bullish on talent acquisition products and services, at this point, just in terms of just being able to maintain double-digit growth as an industry, everything from RPO to products, probably faster than double-digit leads that, you know, at some point, as we start to rebound, I think a lot of these platforms are gonna be taking off. 


Because, you know, the more volatility there is, the more people start to rethink call centers. Right. And talent acquisition is a cost center, it's, you know, it's an expense for companies to continuously have that in the budget. And I think a lot of firms are going to start to think about, like, what are the core strategic functions within our business, right? You have to go to the market you have product, and what functions what cost centers can we start to outsource in a quality way to help maybe even accelerate results in a way that we can't do in-house, but that is also fluid and flexible, that we can kind of scale up or down based on our demands. 


And so I think that the companies that are going to thrive in the future are the ones that have that flexibility and can scale up or down with a company based on demand. And, you know, it's from a business perspective, being a CEO of a company like that servicing that like, I think some people are a little bit scared of saying like, Oh, we want to be that on-demand provider because they're worried about revenue fluctuations, but the reality is like, you just have to make sure that's baked into the pricing, where you can absorb some of those hits and be flexible with your cost structure.                 

But that's really where I see the opportunities like flexibility, being able to scale quickly, right, up and down. And replacing, to a large extent, internal call centers. 


And I think like companies of the future, they're probably going to, you know, have very lean internal talent acquisition teams. And I think that that's going to start to push up into more of an enterprise model as well. And they're going to be leveraging, you know, external partners more and more to kind of fulfill some of those call center functions versus having like big, bloated p&l as of, you know, fixed costs that are long term, right?


Sasanka Atapattu  10:33  

Well, well, two things, right? And I've known you for a while, I'm pretty disappointed. One thing that you just said, right? And for your followers, you know, hopefully there it's hopeful, right, which is, you just said talent acquisition, you know, being a call center, right. And as a CEO, I've had to learn this, right? And what we do know is talent is the most important thing of a goddamn organization. Right? Not the tech, not the drug. Right? All the things I've worked in three different industries, mega industries, right? And we continue to say things like talent is a call center, there's AI for sales, there are all these things that we can do. And the skill gaps and the lack of jobs is going to cost the global economy $1.8 trillion by 2031. $1.8 trillion. And you're saying it's a cost center?


James Mackey  11:33  

Okay, I see what you're saying. But I think like what I'm referring to is like, like CFOs, right? 


Sasanka Atapattu  11:38  

CFOs are, right now my CFO is thinking about rent, he is thinking about flexibility. You're right, I think you guys have a great flexible model, if you think about what I just said, right? 


The TA, the leaders in TA that are progressive, and I know a few of them. Right, that are partners to the CEOs of the best organizations, are adaptable. They're using innovative technologies like lawn sores, they're able to say, You know what, I know this is coming, I'm going to use an adaptable solution that's flexible so that we're about to lay off. But I know Q1 of 2023, we have to hit that number, because the pipeline isn't going to change our revenue goals, we have duties to our shareholders, right? 


So whether you're a startup that's raised money, you have your duty to your board, and so forth, or you're a publicly traded company. And so you're 100%, right, which is, this is what I mean, right? 


Recessions and things of this nature, and words like this create more opportunities for people that want it. And when we look at fields like talent acquisition, it excites me because, hey, if you're in recruiting or talent acquisition, I think for so long they've been left behind. But now, it's a great opportunity to say, hey, you've got solutions, like you guys, secure vision and others that are on the forefront of being the, you know, being a great tool To move forward.


James Mackey  13:19  

For sure. And so one of the other things we wanted to talk about is just attrition in general, right? There are a lot of ways you could tackle this conversation, but obviously, average tenures are declining. People are leaving their jobs faster than ever before. That's a big trend. And that's probably not going anywhere, then we have no, I think you've mentioned like, would you say like 40% of people right now we're considering other opportunities?


So how does that impact? From your perspective, talent acquisition? How does it impact just organizations in general? What do you think about it? I don't know if you consider it a problem or an opportunity. But I'm curious about your thoughts on that.


Sasanka Atapattu  14:01  

So I mean, there are a couple of ways to tackle that. We tackle that in one area. But I think an area we don't tackle that companies really should think about is the employee experience, right?


One of the things as a founder CEO that I'm thinking about is, well, remote culture. But what keeps me up at night is being in a remote culture, you get the opportunity to work with a lot of different types of people and hire people all over the world. But then it's your responsibility as a CEO or founder or leader to recognize that you need to learn about that person's experience, right wherever they are in the world, and make sure that you're doing everything right to create a great experience for that person. 


And today, I would argue, is a broad state that we're all feeling, right? Because we're new at this, right? Because there are different generations and segments and so forth. And we haven't figured out the right formula, right? There's, I think, the emotion of hybrid and so forth. So I think that number one is that 40% of people are looking. Right.


I think that's number one. I think number two is to build your safety net. What is your safety net? What's your plan? You know, and I don't know how you think about that but what you're hearing from your partners or your customers. You know, having an adaptable solution? Is it having a platform? Is it having predictable access? Is it you know, building partnerships, with organizations, nonprofits, that you know, whether that's engineering and so forth? So those are the things that you got to think about?


James Mackey  15:49  

I mean, I think it's more important than ever, like, you have to have proactive solutions in place for talent acquisition. I probably sound like a broken record saying this, but I say it all the time. It's like, the best companies, category leaders, and companies that are upcoming, they do not view talent acquisition as this transactional light switch, they can just flip on and off. 


Like, they're constantly optimizing just like revenue or would or product org would I mean,  they're data-driven, they're proactive. They're investing in a lot of different things tied to talent acquisition, like without getting into all of them, too. But they're, they're just high level like they're investing in it proactively. And I think part of that is particularly for scale positions, right?


Like, you have to not only optimize the entire TA org, but figure out okay, over the next three to five years, what positions are we going to be hiring for at scale, and also specifically optimized for that. So everything from candidate flow to candidate experience, to growth opportunities, employment packages, right, all of that stuff has to be defined first and foremost, for the scale roles, and you have to have the right solutions in place so that, you know, when the market rebounds, you're actually in a position to where you can take advantage of the full wave of that recovery. 


I look at, for instance, you know, coming out of this, whatever this is, whatever it is like recession, whatever you want to call it, this is our chance to become the category leader. Because if we have the right resources in place, now we're going to write that full wave of recovery. And we're going to take over like, that's, that's kind of how I see it.


So I'm less concerned with attrition. I am investing and providing great experiences for employees. Yep. But I also don't care if somebody stays here for a year or three years, stay here, as long as you want to, I will do my best to create the best opportunity for you. I want you to be better off as a result of having worked here. 


And you know, Steve Cadigan. He's the first Chief HR officer of LinkedIn. And I brought him on to my other podcast on acquisition trends and strategy. And he's a very, very sharp guy. He was, you know, head of HR for EA and a lot of other great companies play board directors like 20 firms, right? 


And he says, like, people are trying to solve the wrong problem. They're trying to like to swim up current and try to fight a trend that is 10 years or declining. And he said, whether you like it or not, it's silly to fight that, right? Like that's already happening, and most people don't think that's going to change. What if we flip the script and we started to focus on how we can accelerate onboarding and ramp so that employees can be again adding value faster? 


Like how do we get clear on role descriptions, like the top three things that people have to do? How do we create better, l&d enablement? Process tech says when you know, focus on that problem, if you will, that's the one that's worth solving, because then you can plug people in and out a lot faster. And he also says, like, you know, people undervalue the creativity and energy that new employees bring to the table. 


Like, the reality is that when new people are joining your org at a faster rate, they're coming from different environments, right? Different companies, different challenges that have different perspectives on solving problems, and they can bring that value to your company. So you know, what did the example use, like when he was scaling LinkedIn from like, 300 or 3000 people? The average tenure was like nine months, like, industry-leading category-leading, like just crushing it. So I mean, I'm not saying that, like, we should not strive to create great experiences or to prolong as we should, but I'm also less concerned, I don't try to fight that current, I just kind of lean into it and figure out how do we make the most of it, basically,


Sasanka Atapattu  19:22  

I will back you 100% on that. I think, as an organization, I've lived this right. Launch tours in itself have gone through four or five teams. I mean, I just presented to my team, we've, we've got we're in the launch was 4.0 I've had to reinvent myself, right. 


And, you know, the first time in our history, you know, we have an install base of leadership, and, you know, I've had to rethink, right and that's the toughest thing as a leader and as a CEO that I've had to do right and you're right there's a book alliance of I can't remember, but it's by Reed Hoffman by LinkedIn, he talks about tours of duty at LinkedIn. 


And the reality does become where there just aren't roles right for everybody at each step in the journey and what the theory is, what if you do create this great experience during that short time and not fight attrition, right? But it doesn't mean right still, and I agree with you on that, we still should strive to create the best employee experiences. 


And it'll shake out in one of the two ways, right, which is, you're right, we don't have to fight. You know, people leaving, but at the end of the day, we're going to be left with great employee experiences.    And people will come in, and we can still work on the l&d process, and so forth, we'll just have a better system where, hey, if I can get more people in and in and out of the systems, and I had a great launch source experience, internally, and I left my mark, I have one slide that I show everybody that has like 40 people on it says Leave your mark. You know, I'm a happy person, right? I'm a happy leader.


James Mackey  21:14  

Yeah, for sure. I mean, let's just accelerate the onboarding rant. Right, let's hire the right people, right? Like the metrics should be like, are they adding value? And is the company better off as a result of their work? Are the clients happy, you know, whatever, like, that matters? 


What doesn't matter is necessarily mean, you can have somebody who's with you for five years underperforming. Is that a value? Add that, you know, I mean, like, it just should be less focused on time and more focused on progress, results, outcomes, that kind of stuff? You know?

Sasanka Atapattu  21:43  

Sure. Sure. The question is, how many? How many companies think that way? And are they set up? Right to? To think that way? Right? And at the large organization? Right? Because you're shifting toward and you're right, it is a trend? We don't see people? 


I mean, if you see my LinkedIn, I was at the organization for seven years, right? A big, you know, big, big corporation. Right. And so you don't see that as much anymore. And so our company is going to change and our employees, but it's an interesting argument.


James Mackey  22:21  

Yeah, it is. I mean, again, it's just like, philosophically, how do people view talent? Like, what's their people's philosophy? Like, you touched on this earlier, it's like, you know what you said is like, people are the primary driver of value, right?


Like, that's what's going to allow you to, you know, having the best possible team is going to have an exponential impact on the growth and value that you can provide. Right? So it's just how people see it? Do they view again, like talent acquisition is kind of this transactional thing where the call center that they just cut down on an ad back and cut down and I think the majority of companies out there see it that way? 


And then there's a small percentage of companies that are just like, proactively investing? And my thoughts are that that's probably not going to change. I don't like educating people, it just doesn't work very well, right? I mean, people have their kind of philosophies going into business, like some companies, CEOs, or leaders or product focus on their sales focused, very few of them come from a talented background, right? Like, they're usually like the sales fundraising type that's charismatic, or they're like the product engineering type. They're like, how often do you get the CEO that's like, you know, comes from people, organizations, right, like you do occasionally. 


But generally speaking, you don't, right? So that's like, they're not people who have a tendency to like to oversimplify things that aren't in their lane. And we see that a lot, as I think, as an issue for talent. So like, for instance, like from a client strategy, I just try to stay away from the companies where it's like a hard sell, where I have to convince them and educate them because I just know there's going to be friction in that relationship, they're gonna hire us as the experts, and then they're not gonna, like, let us make the decisions we need to make to drive results. 


And we've just everything from our marketing to our positioning, you know, or like our terms of how we, I guess, like, talk about our value proposition. Everything is trying to just speak to the customers, the companies that already see talent acquisition the way we do versus trying to convince people to see things the way that we do if that makes sense. 

Sasanka Atapattu  24:23  

Yeah, I mean, you know I empathize with you as a GTM person, right? And, being somebody in sales, I haven't spoken to 1000s of sales leaders at this point in research and working with them in LaunchSource. And now I'm new to the talent world. Right. And I have been honored and welcomed by talented leaders that I've been humbled, right, by that world. 


And, what I've seen is, you know, chaos, right, which is, what we, what we mean on the GTM. Side want is efficiency, right? And we want people and we want pipeline and we want sales, but we don't, in what talent is always trying to provide is efficiency process and things of that nature. But it's disconnected and disjointed. So arguably, right? 


You know, I think, that hard sell man, I think it's worth it for just a bigger picture, sometimes right of transforming the organization. Because some of the work that we do isn't just about integrating the platform. Now we're transforming an entire org. Right? We're bridging the gap between the sales or marketing organization and talent teams of some of the largest tech companies. And that's kind of cool, right? And so and that's what you're, you're doing too, but that process is broken. I'm rethinking talent. 


Talent is never even when I think about my financial model, it's kind of a line item. But then I look at all the people I have to hire next year. And then the people after that, and all the mistakes I just made in hiring, and I'm like, I don't even know these people. And I'm calling my friends and talent. I'm like, so is this an account manager? A technical and then they're explaining it to me, my VP of Sales isn't explaining that to me. So that's the type of stuff that I'm learning. And I think, you know, six, seven years in, right, as a founder, CEO, and imagine executives that don't have that knowledge, how much they're missing. 


James Mackey  26:54  

Yeah, they're missing and they don't even realize it. That's the annoying part. There's nothing more annoying than, like a leader or hiring manager that just doesn't know, like, really anything about how to hire the right people, but they like to think they know everything about it, which you find a lot of in talent acquisition. That's like an obnoxious amount of that.


Sasanka Atapattu  27:14  

Transparently met me for years, I just had to pay for it. Right? Like, I literally had recruited people that now are friendly to me that were my clients. And I'm like, What are you doing? Like you're burning your own cash, right? Like, this is the type of person in Hi, this is a profile? Like, how do you know they're like Italian people? Like, Oh, right.


James Mackey  27:37  

Yeah. This is a hearse.


Sasanka Atapattu  27:40  

You have to write a job because then you have to tweak it. Okay, now you hire now, how are they performing? Then they call like, how are they performing? Right, like, so there's a lot more strategic value. And but I think, you know, unlike GTA salespeople, right, that that allowed, I think talent, folks, so do that. And I think I think it will change, I really do. 


Because think about what we've just been talking about, right? If we are saying layoffs are going to continue and people are still hiring, we're going to need the support of talent, it is going to be more critical than ever, to be able to identify the roles. And then if 40% of people are looking to transition in from one industry to another, and people like myself or say oh, that person's great. Like we're gonna hire the wrong people and put them in the wrong roles. It's gonna be a nightmare.


James Mackey  28:43  

Yeah, yeah. And  things are gonna move faster. So it's like without the right process tech, everything in place, like you just there are more opportunities to screw up. Yeah, I mean, that makes a lot of sense that, hey, look, I kind of want to zoom out for a minute, because we have a little bit of time left and be like, you know, 10 more minutes. 


Let's talk about.. what I want to hear like you're just as an entrepreneur, founder, CEO, talk to me about like, the scale that you want to achieve. Like, how do you think about scale, taking your business to the next level? How to go about doing that, like where your head's at, in terms of like, when you're thinking about solving that puzzle? 


Like, what do you see as, like, kind of the big growth levers from a scale perspective to take launch source to the next level?


Sasanka Atapattu  29:33  

Yeah, I mean, it's about decisions, right? At each step of the process. And the decisions get harder because there are things at each stage. 


When you start a company, right? You have more flexibility and fewer customers. You have more flexibility to do what you want and say you're ready to do many, many things or be as big as you want. But then you get a customer. And you have to deliver for that customer and it's your obligation, right? And you need to be successful for that customer to get to your second customer, right? And then you get your second customer, you have to be successful. And it's your obligation. But you know, that's how you get more customers. And we've worked with hundreds now, right? And now we have a base of customers. 


But in our story, what we think about is not all customers are equal at our stage. So we have to think about repeatability and scalability. At our next stage, which customers which levers, right, can we get to? The next tranche? Right? The next million, right? The next set of customers and there are kind of two levers, right? 


It's speed, meaning there's a certain segment of customers for us that we can probably get faster, a smaller deal size, and or there's a second segment of customers that we like we're comfortable with. We've had success with lately that takes a little bit longer. We're gonna have to build some more products around. But they're scaling faster, meaning their average spend is three to four times what I had originally hypothesized. Right? And so what I think about is how quickly do I get to 100? million? Right. And so can I get there in three years?


James Mackey  31:48  

 Right, so you're talking about annually recurring revenue?


Sasanka Atapattu  31:51  

Right. And how do I do that within the new boundaries of SaaS? Within your margins around 70%, you know, within, you know, an expanding 30% net retention, and having a burn ratio, that's pretty tight, right, that eventually hits, essentially, one to one, what Sam Jacobs what people are talking about is scaling properly. 


Which, you know, is challenging because you have to pick the right partners, you have to pick the right clients, right? You have to build the right products at certain stages of the company in order to do that. Right. So those are the levers that I think about at this stage of the company.


James Mackey  32:44  

Yeah, for sure. I mean, like when I think about scale right now, and yeah, I mean, what you were saying? Yeah, since Sam Jacobs had a great post recently, where he was talking about, like, what scale isn't right, right. And he's talking about like, CAC, and LTV and things like those things should be scaling, like scale is not raising money, and then hiring a tonne of people, all right, but then your revenue is not increasing, or your CAC just gets distorted, or like that, you have to there should be you should be looking at a lot of core metrics. 


And those need to be scaling the way that they should be to really, truly make that successful scale, right? Successful scale is not raising money, hiring a tonne of people, and then laying them off three months later. Right. 


Sasanka Atapattu  33:25  

Well, yeah. And, and, you know, I predominantly had to bootstrap and put my own money into this company, right? And I've gone through a lot of pain as you and many people have in building companies, right? This was not VC funded, and so forth. And during that, you learn that because you can't just hire people, right? 


Because you don't have the funds to do so or anyone, and so forth. Now, I've had a lot of great people that have come through here. But I think you've been in a similar boat where you've had to hire within means. And so I think there's a generation of entrepreneurs who are thinking scale differently.


Sam Jacobs is in that same boat, we all kind of look up and see him doing this and talking about it, and it's gonna be a fun ride. In comparing notes each step of the way. The question is, you know, who can do this more efficiently? Quickly, right? You know, because sometimes this takes a little bit longer, right when you're doing it that way.


James Mackey  34:36  

For sure. And that's actually for scale to like, one parallel is we are pushing upmarket as well. Like we're, we're not we are still providing great experiences for our early growth stage startup customers, but we want late growth stage category leaders, mid-market enterprises like we're targeting deal sizes between one and 10 million ARR, because if we can make that a repeatable motion, then then I ultimately am going to hit the revenue targets that I want to see for the company. And that's, we're gonna be able to provide a lot more value for everybody associated with the company at that level of scale. 


So that's, that's something that, you know, if we can crack that code, right, like that is, that's really what we need to do, as opposed to growing very small and incrementally, which is also good. Right? So that but, you know, we want more of those big businesses. We want the projects where we're, you know, assigning 10,20, 30 recruiters to a company. I mean, that's, that's really what we're after right now. 


And so we're, we're starting to see some success with larger projects. But we're still building out repeatability around that. And we want to, like, take it to the next level, right? Like we want to 10x our biggest deal we've ever signed, right? And how do we land that businesses are really like the question and the process and the strategies we're trying to like, you know, think through right now?


Sasanka Atapattu  35:56  

So how are you thinking about that? On your side? You've landed some of these deal sizes much bigger, right on your end. But how do you think about that, when you think about your next 100? Customers are getting 100 million?


James Mackey  36:09  

Yeah, I mean, the kind of approach that I've been taking is pretty much our whole internal leadership team that's full time is like pushing up, right? 


Like they have a strong foundation. And they're kind of moving into their VP role for the first time. Because I want that scrappiness, right, I want people to be able to work with, you know, be resourceful and kind of push up. And it's, it's strategic, but it's also just a lot of hard work, right? 


And so we don't want to bring in executives that they're really smart, and you know, they know what to do, but they needed a team of 10 people underneath them to, to execute on that, like, that's just not what we need. 


So my strategy has been getting those like up-and-comers, scrappy people that are pushing up and fighting and willing to put in the work. And then having like a robust advisory team of very senior people have seen several successful exits have been through scale, that is helping us guide strategy, right at a high level that has been through and, you know, they've been through this stuff and can help us avoid the problem. 


So I invest a lot in advisors, like, that's one of the best, you know, tools that I have dealt with scale like I have an amazing revenue advisor, I have an amazing advisor that is in the RPO space that built and sold an RPO. We're going to be bringing on a customer success delivery advisor that, you know, recently has overseen the build-out of a, you know, over 100 person services company and has a SaaS background before that. 


So we're getting these specialists in place to help us like one. Okay, enterprise sales, let's build a process around that, how do we optimize SMB sales and accelerate that funnel? Right? Three? How do we make sure we don't hit a bottleneck with delivery so we know proactively when we have to promote people in management layers and stuff like that, for a start to think about performance management at scale, we're doing a lot about that. 


And then it's just a motion of like, just trying to stay ahead by like one step. I don't try to look into the future beyond that. But I try to think about, like, what are the problems I have today? And potentially, what do I have tomorrow? And just that motion, but yeah, I think I think what's really when we're going to take off and explode is when we start landing like mid-seven, figure eight-figure deals like it will continue to grow. 


But when we start to dominate, is when we figure that out. And there's, um, you know, someone I'm speaking to, like another advisor that, you know, she might come on is like, you know, like a full-time employee. And her background is in this space for 15,20 years, few successful exits, and she's, like, hands-on enterprise sales, like the big stuff, like she doesn't want to, you know, she doesn't want to deal with like the, you know, 100k to 300. Like, she's like, No, I don't I'm not going after that stuff. I'm just focusing on like enterprise fortune 500,  that seven, eight-figure deals like that's what you know, she's going to be focusing on so right now I'm working on having the margin to bring her on, right, like, trying to figure out how to make that happen? And when's the right time to do that? 


Because obviously, there's a lot of uncertainty. How aggressive do I want to be? You know, do I want to make that higher? Now? Do I want to wait a few months to see, kind of like, what happens in the market? So a lot of what I deal with too, when it comes to scaling is like trying to think about timing. Like when's the right time to make strategic decisions, strategic hires, like what should my margin look like at scale? 


Because I have to be profitable as Bootstrap. So it's like, how fast I need to increase my cash balances to like, what correlation to the cash balance be to our expenses and like, you know, when's the right time to make certain strategic hires and then calling your shot right, like, how confident am I that this is going to be huge glute growth lever if we make this big investment. So more and more I feel like my job is forgetting about judgment when it comes to timing, and being able to call my shots and like which global growth levers I am most confident in, are going to hit, and just trying to not make any mistakes that can kill us, right? 


So I just tried to bring in the advisors and try to get everybody's thoughts on, where are the biggest opportunities to explode, right, and in a good way, a good explosion, a positive explosion that increases.


Sasanka Atapattu  40:24  

So it's interesting, you have it, you think it through that way. So for me, I don't have a shortage of advisors. But I always have a shortage of cash for all the things I want to do, right? And I think anybody does, right? It's all about decisions. 


And probably the most impactful thing or one of the most impactful things is, you know, securing and testing, I went through a couple of iterations of this. A finance lead, right, who ultimately right now is my CFO. And I think we talked about this a little bit, who gave me the confidence to hire, you know, a heavy hitter, who also happens to be an advisor, friend, so for the VP of sales, that I will say, like, change, really change the game, right? In terms of a couple of different things. 


Now, a couple of things to think about are when you hire a sales leader, think about that immediate impact you want, versus today versus what you want, you know, for the future in the company. And the reason I say that is we built a foundation, which allowed us to take a step back, versus sell, sell, sell, sell, sell, sell because we're both enterprise people that can sell. But we built a foundation, built camaraderie with this team around us. And we came together that gave me and this team the confidence to 5x this thing, right? More than if we just got three or four deals. 


So that's something to think about when you think about timing, is making sure you have the foundation to bring in those enterprise deals, not just that one, but how do you bring the second one? How do you bring that third? How do you bring the fourth, right? And it took somebody and a couple of people to think about it differently, not just one person, right? 


And that was an investment in not just dollars, it was an emotional investment on me to say, I need to like step back to say, It's okay if we miss a little bit on this revenue target that I'm very, I don't miss revenue targets, because I'm bootstrapped. So I don't miss ever revenue targets and I'm, you know, and so forth. But we're so much better for it. 


So I think those are the things that, you know, I think about, but I think financials go hand in hand. And that even gave me bigger confidence to invest in the product, which, you know, I'm testing out and we've, we've brought on a product lead right now VP of product.


James Mackey  43:39  

That's awesome. Yeah. Having the right financial advisor, right, whether it's like a CFO or just like a high-level finance advisor, or whatever it might be, it's such a game changer. Like you can be so much more confident and quick to act when you have the right budgets and forecasts in place. 


And you understand the finances on a whole other level, like, Yeah, whenever I have a big spending decision to make now I just immediately hit up my finance guy, and I'm just like, aren't we walking through this? And also like the best finance people are strategic, like, they go beyond numbers on the p&l. And they actually like they'll, from past experience, be able to say like, oh, here's typically how this ROI goes, or here are the holes, you can follow this type of investment, that type of thing.


Sasanka Atapattu  44:19  

Exactly. And for our stage, right, like, some things need to be done right and things it was just the right fit, right. And it ended up being more than just a finance person, a great partner. So to the business and so it ultimately rounded out our team, which, arguably is I mean, you know, we're in a spot where it's, it's, it's, you know, it ends up making decisions a lot better. 


So, it rounds out what you think about when you're thinking about that enterprise hire. I think there's a lot of things to think about right which are, you know, Yeah, the market all those things, but how is that person going to influence all those components in your existing team? How is that gonna affect six months from now? The team, you know, 12 months from now and you know, your next 10 deals should you know when she brings them in? 


Because now that's what I'm thinking about. You know, I know he's going to be successful. But the team that he builds, what's that going to look like? Right? Resources?


James Mackey  45:29  

Yeah, that's where it's like, yeah, having that advisory layer. So there's like an extra set of eyes. Yep. Well, hey, man, look, this is great. Like, I can keep going. But we're up on time here.


And so I just wanted to say, you know, thank you for coming on. This has been incredibly valuable. I appreciate your contribution. And I know Dondre CEOs tuning in venture capitalists, everybody, product GTM. People are going to learn a lot from this conversation. 


So thank you for sharing your thoughts, your perspective, and your experience with us today.


Sasanka Atapattu  45:57  

Hey, thanks so much for having me. And it's always great chatting with you. I'll see you on the other side. Hopefully, next time, live in the next event, and have an awesome Friday.


James Mackey  46:07  

Let's do it. Real quick, though. Before we jump off, could you tell everybody where to find you if they want to engage with your company or with you directly?

Sasanka Atapattu  46:13  

Absolutely. So you can find me on LinkedIn, Sasanka Atapattu. And you can reach me at Sasanka at Our website is So simple. So thanks so much.


James Mackey  46:36  

Yes, for sure. And for everybody tuning in. Thank you and we'll see you next time. Take care.

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