In this episode, I talked to Shruti Kapoor, the co-founder and CEO of Wingman, a SaaS product that helped sales teams get better results by providing them with real-time insights from every sales interaction.
In 2017, Sruthi was working for a FinTech company in India and ended up running a sales team, but she constantly struggled to get the CRM to work the way their team needed. And she couldn't find a good alternative solution, so she and two friends got talking and decided to start their own startup.
The following year they launched the first version of their product, but getting customers was a struggle when they started out. Their first 40 meetings with prospective customers resulted in zero sales. Despite the rocky start, they've grown their SaaS company to multiple seven figures in ARR and in 2022, sold the business.
In this episode, we talk about the struggles and challenges the co-founders faced while starting and building their SaaS business. What they did after failing to close even a single sale after 40 meetings with prospective customers, how they've used online groups and communities to find customers by getting their existing customers to post and talk.
And we talk about how they've used SEO, content marketing and social media to create an inbound marketing engine that drives over 90% of their revenue today. I hope you enjoy it. All right, Shruti, welcome to the show.
And I think that's an important lesson in life overall you know, not just for founders.
One, get sales folks better coaching feedback to enable them in real time. So as they're going through a call, if you could get the feedback versus, you know, waiting for the manager to review the call a week later and then, you know, maybe have a coaching session two weeks and three, it enables people to get a full picture of what their pipeline looks like, where their deals are so that they can go and, you know, make sure that they're doing everything that they need to win.
Decided I wanted to get my hands dirty with startup. Joined a FinTech company called Payoneer and, you know, figured that I would be best suited to figure out their go-to-market strategy right knowing absolutely nothing about go-to-market strategies. And at that point, you know, what that meant was working with the product and the marketing teams and of course creating the sales team, going out and selling myself and trying to get those early customers for Payoneer in India.
And through that process I kind of realized some of the challenges you know that I'm trying to solve with Wingman. One of them was definitely not knowing why certain sales reps in my team were doing so well, and some reps who were putting in a lot of effort but still not getting the numbers.
So, I think that's kind of where I got curious and said, listen, I want to join your calls, but then it becomes too onerous. You know, one out of every two or three calls will get canceled. You waste so much time. And so, I was like, you know what? If they could just record their calls and then I could go back and review it.
But the other challenge was that because we were a distributed team, we have product and marketing sitting in Israel and then, you know, sales sitting in every country that they were selling to. And so, the other challenge that I was frustrated by is getting the voice of customer over to product.
So, I think both of those as I thought more and more about it, I was like, you know, if we could only have these calls recorded, archived, searchable that would be a gold mine. And that's where the journey started.
Like, how do I get value out of this data? Because we understood that this was valuable data, but you know, this is such a large volume of data. The last thing we wanted was that you have all of these call recordings and then you know, nobody is listening to it. So, I think we spent some time in just understanding what the real challenges were, validating that it wasn't just a problem for me.
And then, you know, trying to kind build our own MVP. What would an MVP look like?
And so that's the context with which we got together. And you're right, it, it took some time for things to come together. So, you know, we met almost a year and a half before we started up. And so, through that period, you know, we were just hanging out, getting to know each other.
Brainstorming on a bunch of ideas, trying to validate, invalidated a bunch of ideas. And Muralid and Srikar have known each other since their first jobs out of college, and they were also at Google together. And so, Muralid was very clear that he would want Srikar to also be part of the team when we started off.
And he managed to convince Srikar to also quit his job and moved from the Bay Area to India to start this up,
Right? So, what we felt was, one, nobody had a clear thesis or understanding of how to use this data. And we felt that, you know, the winner wasn't just because somebody decides to record calls and transcribe them because, you know, recording of calls has existed for at least, you know, a few decades. Right?
We felt that the real innovation or you know, where the business needed to be built was. Identifying the right use case for the data and being able to make sure that you're able to deliver that value quickly. And we felt that was not answered when we started building this out, and you know, when we were trying to validate whether or not that was answered, we went and also spoke to some of the customers who were using the computer competitor's products because we wanted to understand like, Hey, if you're using this today, does it solve everything for you or are there still gaps? Through that process, we identified that there were definitely things people were struggling with. And I think that was also an important learning in just knowing that, you know, what people say they will do in an ideal world versus what people do is dramatically different, right?
Like I, I know we are all familiar with New Year resolutions and how they land up. And that was exactly the case with sales coaching where, you know, I think the products were built on a promise of saying that, hey, Sales managers are motivated to do sales coaching, and I will build a tool to help them do sales coaching better.
But the fundamental problem was that sales coaching doesn't happen as often as people would like.
How long did it take to build that 1.0 version of, or the mvp, I guess, of Wingman?
Five months.
Yeah, I mean, that sounds great. You know, you ship the product, you already got one customer and you get excited and you're like, wow, we're gonna be closing more and more of these deals. But from what I said, it wasn't that straightforward.
When you talk to a lot of potential customers and you didn't close any sales. So, so tell us about that .
You know, from our network, right? So, these were not customers who we did not know, and therefore you know, these were really useful customers for, you know, as co building partners and, you know, for giving us early product feedback, et cetera. But what we wanted to do was to, of course, and you know, you need to do that.
Is make sure that you actually also reach out to customers who are buying the product for the sake of the product and don't necessarily know you. I think the first challenge that we hit was even with these friendly customers that we had early on, they were not using the product the way we would expect them to.
Right. So, we were hitting the same roadblocks in terms of product usage. And you know, that was baffling, but I think that was also our own lesson in understanding that, you know what people say they would do, and what they actually do is different. And so we had to kind of go and really sit down, understand what their workflows look like, tweak you know, the product, understand what is the first, you know, wow moment we could deliver them and you know, how do you make that repeatable, et cetera.
So there was some work required there. The second thing we did was, like I said we kind of went and spoke to people who were using the competitor's products and understood, you know, what were the challenges they were facing? Was it a product issue or was it just setting the right expectations?
And then what we did was once we felt we were ready to kind of scale up, we you know, at that point we launched. Dramatically new feature for the product, which was this whole idea of being able to give real time feedback to salespeople while they were on sales calls. And we felt that was, you know, going to hit the nail on the head.
That was allow going to allow people to actually coach without being there. And we were you know, ready to kind of take it to the market. So we got a sales consultant to help us you know, accelerate that process of reaching out to new customers. And that person set up you know, great meetings for us.
He set up 40 meetings with our ICP companies and, you know, we, we sold exactly zero to those 40 customers and we were like, you know, something's not right. And that was really tough because we felt at that point, you know, we had a good product, we had a real differentiation and we were talking to the people that we wanted to be selling to.
And so that was the point where we were like, you know, there's something that we need to go back and think about. And I think what we realized at that point is you know what the product does right and what the promise is. Sometimes as founders, we tend to oversell the promise as well. But what we don't account for is, you know, how the customer is thinking about it in terms of.
Their implementation costs or effort required to get value out of it. So that was the challenge that we were facing in getting people to, you know, adopt this new real-time feedback mechanism. And so, you know, once that became clear to us we were able to kind of go and make changes to say, how do we make this easier and quicker to get value out of?
Give me one example of that. Like what was it that was, that you realized they were seeing as difficult to implement and get started with? Like, what did they have to do that they didn't want to do?
Right. So if somebody says you know, talks about discount, then we want like, these three talking points to show up for the salesperson. And that was what we needed sales enablement to do but this wasn't something that they were used to doing because they're used to, you know, creating content either for trainings which is typically long form or, you know, self-service content, which is, you know, these detailed documents.
They're not used to writing like three bullet point pieces of content. But the other struggle that they had was they did not, they were also not kind of sure whether they knew what content they. All right. So, so to them it seemed like they needed to invest in something without fully understanding, like, you know, how that would work or how that would get them results.
And I think it was also a case of, you know, the stakeholder who was going to be the decision maker versus the person who needed to actually implement the product and get value were different people and, you know, we didn't kind of know how to navigate that well. And I think that was, a reflection of you know, us as founders because none of us had actually worked in SaaS.
Right? None of us had actually also worked in a situation of understanding how a multi-stakeholder, you know, product adoption cycle looks like. And you know, how do you kind of navigate that from a sales and post sales point of view.
So that's kind of a difficult leap to make. So, so how did you solve that? I mean, that's, I think this is something that a lot of SaaS founders go through that the perceived work, even though the customers might not say it, and it sounds like the 40, or at least the 39 people you spoke to, weren't that explicit about it.
But it's, I think it's a common problem. So how did you go about solving it?
So in our case, like with the real time feedback and you know, just having a real time note taker there we identified that, you know, giving feedback on behavior did not require any setup. So I could have something that tells them that, Hey, you've been on a long monologue and we didn't need the manager or anybody else to do anymore.
Similarly we could, you know, use, get them to bookmark parts of the call in real time without, you know, managers or setup needing to do work. So one was identifying pockets that required minimal setup, and using those as the hero examples in those sales conversations versus, you know, using all these complex things that required a ton of setup as the hero example.
So it was easy for somebody to say, oh, I can instantly get value. Without putting in a lot of effort. And then if I wanted to put in effort, you know, this is what I could do. Right? So essentially constantly being very diligent about saying, how do I create a wow moment with minimal effort so that then the person, once they see the value, then they will put in the effort.
I think the second thing we did was you know just taking away a blank canvas approach and saying, we will give you enough in the canvas so that you only need to fill in the blanks. So, you know, basically creating all sorts of templates that made it much easier for people to say, oh, okay, I only need to write these three bullet points.
I know what the use case is. And in some cases we would even use you know, like different methodologies, different sales information that existed to create you know, that set of templates and initial things for them. So again, trying to get, give them value before we ask them to invest effort.
So we are still trying to figure, trying to figure out the positioning value, et cetera. And so at that point we did like a bunch of more you know, larger scale launches. And through that feedback cycle we realized that there were some people who were buying the product and not using it for this specific use case.
So we were like, you know, the first thing we did was. Became open to saying that we could have different packages of the product for people who might have different levels of tech readiness. So that allowed us to at least start getting some customers who did not necessarily want this complicated feature and who did not care that there was, you know, maybe not a big differentiation story, et cetera.
Right? And in the meantime , thankfully the changes that I talked about weren't so much product changes. They were more positioning and conflict changes that, you know, we didn't need longer cycles for. So we were able to quickly iterate on that and like we spent you know, the next four, five months just saying that, we'll just, you know, customers who are interested in buying, we'll just try to listen to them, understand what they're buying for, what they're using the product for, versus trying to get people to adopt everything that we are trying to build on day one. And I think that really helped in you know, getting to the juicier parts of the product.
I think the second point was that we were very clear about what our differentiation was. Yeah. Right? And that was around saying, can we actually help people scale coaching? The third thing was that I think we had also spent time and energy in understanding how we might be able to use our geographic advantage and distribution.
To actually deliver better value for the customer. So in our case so, so there were basically things around saying how do we make sure that we are going to continue to be competitive? And it's not just about, you know, one feature versus another. And I think those were things that YC really cares about.
Like what is your long-term you know, chances of success and why?
All right, so we kind of went from, I said, you know, close to zero to six digits in revenue very quickly at that point. And that was, you know, within the matter of those three months or so. From there on you know, we kind of felt that what was working for us was having you know, some sort of inbound funnel or customers because what had worked in getting some of these was you know, we did like a product hunt launch and some you know, some early P R that happened around Visim.
And so, what we realized was that we then wanted to start building on that inbound engine. Because, you know, maybe we were not ready for some larger customers. We needed to still build more trust in the market, but we could still be selling to you know, the smaller end of the customers to start with and then you know, work our way up.
Which we then very often you know, even for our inbound funnel and marketing overall. We did also get some customers through the outbound engine early on. But what we realized was that inbound seemed like, what could be much more scalable. Of course, early on it was, you know, me as the only person doing sales and marketing and SDR and, you know, all of those fancy things that we have teams for today.
And I think, therefore, my approach was to say how do I spread the message across based on what I understand about the sales leader’s buying behavior. And I think that's something that people miss on sometimes, you know, you kind of reach out to multiple people for advice on, hey, how did you get your first 10 customers or your first 20 customers?
And people forget that, you know, if you're selling to a salesperson versus to a developer you know, the way they buy a product, the way they evaluate a product, the way they think about the product is very different. And so what we realized was that salespeople one, are very social right?
And they like to talk to each other, and they like to get you know, inputs from each other. And a lot of what happens in sales is through word of mouth. And so we kind of just doubled down on that and we said, Where are people giving each other advice and sharing this, right? And so, this was already you know, by now we are already in the times of the pandemic, and we are beginning to see that, you know, there are all these online communities that are popping up.
And I think that landed up being very fictitious for us because we were then able to get you know, spread that word of mouth using those communities, those online selected platforms versus just trying to do Google ads or, you know, G2 ads, et cetera.
Yeah, so this was, you know, like lots of revenue leaders, slack communities that existed. You know, there are lots of forums were revenue leaders exchange advice. You know, there were Reddit threads that our customers saw where, you know, people are asking questions around, say, price of a competitor, and they were like, hey, you know, we use this tool and this is why.
And so, you know, it was very niche targeted communities through which we then built the word of mouth.
One thing that a lot of people do, which isn't particularly well taken, is going into a new community that you just joined and just start pitching your product. So, what was the approach that you took if you were telling people about Wingman, how did you get to that point where you were doing it in a way that you know, people were more receptive to it.
And I think when you and I were talking, you were saying that you were also getting customers as well to help with, you know, amplifying this word of mouth. So just tell me a little bit about that because there's a right way and a wrong way to do this, and I want to kind of figure out what you did.
Like, they don't even have to say anything else. Even if they say, you know, if there's a thread around, hey, what do you use for doing this task? And somebody says, oh, I'm using this, you're much more likely to go check it out versus saying, hey, I'm the founder of and you know, we also do this. So, I think through that right, what we were really looking to do was just amplify the word of mouth from the customers, right?
Like, you know, in the real-life situation, we would've expected this to happen through events and through casual networking, you know, social settings. And you know, what we were thinking of was just, you know, today, nobody can step out because of the pandemic. How do we leverage what exists in terms of still spreading the word of mouth?
And so, it literally started out that way. Some of our customers initially found like some threats saying, hey, you know, I saw this discussion you know, would you want me to say something on this? And we were like, oh, that's fantastic. And so, it was not us posting about ourselves, I think, which definitely helps.
And I think our role in that was really. Identifying where those discussions were happening at some point, and then nudging our customers if needed to say, hey, you know, do you mind just, you know, sharing what your experience has been? Yeah, and I think that worked. One of the lessons that we, that I overall learned in that journey of getting, you know, the first five customers to try to scale that up through inbound was what you really need throughout that journey.
One thing that is common, how do you build trust and as you try to scale, how do you amplify that trust through various ways? And I think that was a big learning also from saying that, hey, we hired the sales consultant early on. You know that person was able to set up meetings for us, but we are not able to close.
Partially also because that trust doesn't translate. And especially if you're hiring somebody part-time. I think that was that was a big lesson and therefore as we went through this journey, we were always very conscious about, hey, how do we build trust? And how do we continue to scale the ways for building trust?
So, so people listening to this can understand like how much volume and sales you're actually driving through your inbound engine now?
You know, today of course, we do invest a ton in content. , our approach to content has been can we do something that people actually laugh at or relate to, versus, you know, some more corporate jargon. And I think that has landed well. So, you know, we do partnerships on Instagram around, you know, fun memes on sales, things like that.
Just a bunch of educational and thought-provoking posts on social media. So, I think social media is one channel that helps us build brand and be present in conversations. And I think the other piece has definite, so, you know, the other piece has definitely been SEO as well. As you know, things have scaled up and I think today we have a pretty strong game there.
And I think the third piece has definitely been you know, continuing to focus on personal brand you know, for the leaders and for other folks in the marketing team because I think that's super important. And so, we make sure that you know, folks are visible and yeah, I think personally I've probably you know, interacted with a lot more people being on several social campaigns, podcasts, et cetera. And that I think again, helps you know, create that recall and brand.
It seemed like sales tech was on a consolidation spree. We were definitely getting that feedback from the investors we were talking to as well. And, you know, within a matter of couple of weeks, we happen to get inbound interest from three different buyers. And you know, we haven't started thinking about it, but you know, I was like, hey, maybe there is something here. Let me just go and dig a little bit deeper.
And so that's kind of how that conversation started. And I think you know, as a founder, that was something that I was open to at that point just in terms of you know, the fundraise cycles you know, it always makes sense to consider an acquisition.
You know, before you do a fundraise work, you know, you can't really get acquired immediately after a fundraise because your investors won't be very happy about that. So, I think in that sense, the timing was good. And so I decided to take a pause and just, explore that a bit.
Fundraising can be pretty distracting. We did you know, try to fundraise. , you know, in 2020 mid of 2020 or so. And then I think what we realized was with the pandemic and, you know, sales teams getting laid off we were seeing like, you know, ups and downs in our own business and in the revenue numbers.
And what that eventually meant was it wasn't the greatest time to try and fundraise. And then I think, you know, later a lot of times investor sentiment impacts these things. Right. And then as it happened, and the second time that we tried to fundraise was in the middle of the and you know, when we started things were stable, but then suddenly, you know, the whole Delta variant came about.
And like, especially in India, it was pretty bad. And investors were just focused on like, you know, helping people actually survive, and it wasn't, again, the greatest time to fundraise. So what you realize is that, you know, sometimes you can't really control the timing on these things, you know. In hindsight, if it works out, then it's great.
Right. Like if you're able to fundraise at the top of a you know, valuation cycle but very often you know, as many things in business, it lands up being a little bit of luck.
