Founder-Led Sales: From 2% to 20% with 10-Hour Custom Demos

Summary

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The SaaS Podcast: “Founder-Led Sales: From 2% to 20% with 10-Hour Custom Demos”

Host: Omer Khan
Guest: Jaeger Kumaraptan, Co-Founder & CEO of Paperflight
Date: May 14, 2026

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Episode Overview

This episode of The SaaS Podcast dives deep into the founder-led sales process that propelled Paperflight from struggling to close any customers to reaching seven figures in ARR and winning 500+ B2B clients. Host Omer Khan speaks with CEO and co-founder Jaeger Kumaraptan about how Paperflight’s relentless, hands-on demo approach dramatically increased conversion rates, how the team won enterprise deals with zero previous sales experience, and how founder commitment and feedback loops shaped both product and go-to-market strategy. The conversation is rich with practical insights for SaaS founders at any stage, including points on inbound traction, customization, competitor dynamics, and the evolving role of AI in SaaS.

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Key Topics & Timestamps

1. Founding Story and Inspiration ([03:10] – [08:02])

• Origins: Jaeger and his co-founders drew on their prior experience with digital collateral at Cognizant, realizing a major gap in how marketing content was distributed and measured in enterprises ([04:32]).
• Problem Identification: “We did look at every single product that was available in the market back then. None of that would do justice to the kind of collateral we had built… So it was a problem that we already knew.” — Jaeger ([04:45])
• Transition to Startup: The exposure to startup culture and technology feasibility while at Cognizant inspired the leap to entrepreneurship ([06:08]).

2. Finding Product-Market Fit and Initial Funding ([07:34] – [09:19])

• Prototype-First Approach: The founding team built a prototype based on their intimate understanding of the problem before seeking investment ([07:34]).
• Customer Validation: Early demos elicited positive feedback from marketing leaders, but did not lead to deals immediately.
• Quote: “When we validated this... the response was pretty good. So everybody was like…the experience is really good. We will buy it. That was the start.” — Jaeger ([08:02])
• Reality Check: “Did they buy it? No.” — Jaeger, emphasizing the disconnect between positive feedback and early sales ([09:20])
• Lesson: Feedback is necessary but not sufficient; early-stage sales are much harder than optimistic signals suggest.

3. Paperflight’s Product & Value Proposition ([10:51] – [14:38])

• The “Netflix for Content” Analogy:
  • Seamless, personalized access to collateral for sales reps (contextual content and telemetry tracking buyer interaction).
  • Actionable analytics for sales teams to know when and what to send to prospects ([11:57]).
• “When you log in, you really see all those pieces of content... Most successful sales reps use this content or this is what you should share at this point in time and in this deal stage.” — Jaeger ([12:30])

4. Winning the First Customers: Relentless Inbound and Community Engagement ([14:38] – [19:05])

• First Sale via Inbound: Initial customer came from Intercom after interacting with the product; involved an S&P team for a major climate conference ([15:10]).
• Content-Led Inbound: The team’s early traction came from answering questions in Quora, Reddit, and forums — leading to highly qualified inbound leads.
  • Quote: “The first couple of years, we spent a lot of time on forums, on Quora, on Reddit, responding to questions, tagging the platform. This was the primary responsibility of a small team…” — Jaeger ([17:38])
• ICP and Vertical Focus: Early target was heads of marketing and CMOs, not limited by vertical, to capture maximum learning and opportunities ([19:09]).

5. Founder-Led Sales Process: High-Touch Custom Demos ([20:41] – [27:36])

• Heavy Lifting Onboarding: For each prospect, the Paperflight team thoroughly researched, aggregated, cleaned, and tagged company-specific content to create fully customized demo environments, sometimes investing 8–10 hours per demo ([22:49], [24:56]).
• Conversion Data: Running A/B tests between the high-touch and generic demo approaches revealed a dramatic lift:
  • Generic demos: 2–3% conversion
  • Custom, tailored demos: 17–20% conversion
  • “It was night and day.” — Jaeger ([25:58], [27:09])
• Memorable Moment: Investing substantial engineering and ops effort—even when the company was nascent and money was tight—paid off through learnings and conversion rate.

6. Bootstrapping vs. Raising Capital ([27:37] – [32:18])

• Minimal Funding Path: Seed round of $400,000, then profitable — avoided future fundraising despite major market opportunities ([03:31], [27:37]).
• Rationale: “There was a lot of freedom for us to decide on how we'll operate, what we'll build…as long as it doesn't restrict from a commercial standpoint, as long as we're not tight, we were fine.” — Jaeger ([29:48])

7. Navigating Competition: Big Players & AI-First Challengers ([32:30] – [40:32])

• Facing Giants: Entered a market with billion-dollar players (Seismic, Highspot), now directly winning deals from them ([33:03]).
• Consolidation Dynamics: Recent seismic-highspot merger is simultaneously clarifying (a single major competitor target), but market is noisy with new, pointed AI solutions ([35:11]).
• Product Positioning:
  • On par with both large incumbents and nimble AI startups; focus is on blending industry pedigree with bleeding-edge AI features.
  • Quote: “Our products have actually evolved…I'd really say it's a sweet spot or the best blend of expertise and experience in the industry and the advancement from a technology standpoint and the capability to move faster forward.” — Jaeger ([37:59])

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Notable Quotes & Memorable Moments

• On why custom demos work:
  “When I build the entire Netflix-like experience and on the demo call ... when we show them, here's how your hub can look like… That's the first aha moment. That's actually when you tip them, that's actually when the conversion happens.” — Jaeger ([22:49])

• On founder bias:
  “It's very difficult for you to split the view between how you look at the product versus how your users look at the product … In times where we have not watched out for how whatever we built is being used, we've lost time, we've lost revenue.” — Jaeger ([43:09])

• On product alone not being enough:
  “You build a really good product and you watch and the product will make the sale. Or that's going to help you just do everything? I don't think so. You've got to have an amazing team. You need to have a plan.” — Jaeger ([42:22])

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Lightning Round Highlights ([42:08] – [44:11])

• Advice disagreed with: Product quality alone drives sales.
• Recent impactful read: Dario Amodei’s essay “Machines of Loving Grace.”
• Hardest founder lesson: Product perception gap between founder and user.
• Time-saving habit: “Notion. I've got a lot of notion boards.”
• For fun: “I run. I love good design. I want tracks.”

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Key Insights & Takeaways

• High-Effort Customization Drives Conversion: Spending 8–10 hours tailoring demos to the prospect’s real environment (even with no guarantee of sale) can 10x conversion rates for early-stage B2B SaaS.
• Relentless Community Engagement Fuels Early Inbound: Hanging out and answering questions in niche online communities is still one of the best levers for early traction with highly qualified leads.
• Iterate with Experiments: Constantly A/B test onboarding, demo, and outreach strategies—be prepared to change tactics as you grow.
• Product-Market Fit Is A Moving Target: Even positive feedback from the right users doesn’t guarantee early sales—be prepared for repeated iterations and hard-won trust.
• Freedom vs. Fundraising: Bootstrapping can bring freedom, clearer vision, and product focus—provided growth is sustainable—while recognizing that distribution (not just product) is increasingly a key differentiator.

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Listen To This Episode For…

• The actual playbook that helped a SaaS founder boost early demo conversion from 2% to 20%
• Tactical details on scaling inbound using community engagement
• Fresh founder perspective on why and how to stay customer-obsessed and high-touch through growth stages
• Honest talk about bootstrapping in a world of giant incumbents and AI-native disruptors

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Find Paperflight: www.paperflite.com
Connect with Jaeger: LinkedIn (link in show notes)

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End of summary.

Transcript

[Omer Khan]

Welcome to the SaaS podcast. I'm your host, Omer Khan. AI has changed the playbook for building and growing SaaS. Every week I talk to founders who are writing the new one.

For the first two years they couldn't close a single customer, so they spent their time on Quora and Reddit answering questions from people they were trying to sell to. And eventually that's how they landed their first customer. My guest today is Jaeger Kumaraptan, who along with his two co founders built pay per flight into seven figures in ARR with 500 B2B customers. In this interview, he breaks down how spending eight to 10 hours on every custom demo helped them push their conversion rate from 2% to 20%, how they signed 26 enterprise customers in one year with zero sales experience and and how a Fortune 500 deal almost died in their Intercom inbox.

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All right, Yeya, welcome to the show.

[Jaeger Kumaraptan]

Thank you Omer, Nice meeting you.

[Omer Khan]

Same here. So tell us about Paperflight. What does the product do? Who's it for?

[Jaeger Kumaraptan]

Paperflight helps marketing teams reap ROI for their content. And all of this private knowledge is also used for sales enablement from a sales. From a sales revenue standpoint in terms of closing deals faster and scaling up revenue.

[Omer Khan]

Great. Give us a sense of the size of the business. Where are you in terms of revenue? Customer size of team in terms of revenue?

[Jaeger Kumaraptan]

We're in seven figures. ARR. We've got around 500 odd organizations, B2B enterprises that use our platform across the world. And We've got around 140 employees, primarily headquartered in India and there's a small team based out of the US and

[Omer Khan]

so from what I understand, you guys founded the business in 2018, you raised a seed round of around 400,000 and then after that you haven't raised any more money and the business is profitable.

[Jaeger Kumaraptan]

That is correct. That is correct. So we raised a seed just for us to get us off the ground. And then a year into year in, we turned profitable and our Runway was clear and we did not have the need to raise capital after that.

[Omer Khan]

Okay, great. So tell me, where did the idea for Paper Flight come from?

[Jaeger Kumaraptan]

So before, before we started pay per flight, one of my experiences was we built a crowdsourcing platform back in 2015, which was entirely new for the industry at that point in time. A completely new product that we were trying to take to the market. This is part of a larger organization I used to work with Cognizant before. This was a venture that was running back then. And this was an entirely new product that we're taking to the market and which means we had to build a lot of awareness. So we had to create a lot of collater. And distributing all of this collateral to the GTM teams was very important. And we did look at every single product that was available in the market back then. None of that would do justice to the kind of collateral that we had built. Videos and brochures and case studies and white papers and everything. So it was a problem that we already knew. But then we split ways, went in different directions as founders and at some point when we wanted to start something, we did experiment with multiple possibilities of what, what we could work on. But this was a problem that was at the back of our hand. We really knew what was there, what the market had to offer and how different we could solve as well. So that's how we started Paperflight.

[Omer Khan]

Okay, so you and your two co founders, you guys were all in full time jobs at the time and so what was the, the moment where you said, yeah, let's leave the comfort of all of that and let's go all in and start building this business.

[Jaeger Kumaraptan]

So after the venture that I just described right now, I moved to New York. I was heading technology prototyping and we were working with brands like Ford and Lego and Nike of sorts, and we were building technology feasibility assignments for, for how these brands would look like, like 15 years from now and 20 years from now, what kind of technology would they need to put on the field? So that kind of exposed us to a lot of startups, the entire world of what's possible, the technology that was available and how different each of these solutions are coming across. If you put these two together, the problem that we already knew and the exposure for how these, how the startups are being, are being built, put together was kind of a good motivation for us to look at. If we were to solve a problem that we really knew well about, could it be, could it be solved in a different way? Could it be solved in a more effective way? And we were excited when we landed on how Paperflight solved the problem to start with. We were really excited and that's what got us to starting something on our own.

[Omer Khan]

So did you guys go and raise the seed round first? I'm trying to figure out like when, what was the order? Did you kind of like self fund, try to build the initial product, then later raise a seed round?

[Jaeger Kumaraptan]

We had the prototype, we had the idea, we had a prototype, a working prototype. Not something that's scalable, I'd say, but working prototype that we could demo and that's when we raised the seed capital.

[Omer Khan]

And what was that demo based on? Did you go out and talk to prospective customers and get feedback? Did you validate the idea or was this just more based on. This is our own experience and we're going to solve for that.

[Jaeger Kumaraptan]

It was our own experience that I think is very important because you need to be rooted to the problem and the solution and you need to be, you need to have that conviction to how you're solving, that's just start. But then validation is very, very important. So when we solved the content problem we picked up on before we solved it was all in folders and SharePoint and Box and Dropbox. And that's the best way to distribute content at that point in time. When we started Paperflight, we went after the heavy content platforms like Netflix and Amazon of sorts. And we said when you log into the platform, you will have a Netflix like experience, which kind of gives you the content depending on the product that you're working on, the region that you're working on, the segment of customers that you're selling to, so you don't have to drill down through folder structures and figure out what's new, who's uploaded what, what's working and all of that. So that was the experience that we built. And when we validated this solution, the prototype with actual users in marketing, head of the CMOs and head of marketing, the response was pretty good. So everybody was like, we've seen something like this. The experience is really good. We will buy it. That was the start.

[Omer Khan]

Did they buy it?

[Jaeger Kumaraptan]

No.

[Omer Khan]

Why do you think that was in the early days?

[Jaeger Kumaraptan]

There are multiple reasons. One is they're possibly leaders in marketing in much larger organizations and they wouldn't want to subscribe to a platform that is just coming off the ground just now. They'd want us to watch for some. They want to watch us for some time before they could pick us up. The other reason was, I mean, I think always there are promises and when you really hit the ground, it's harder. It is 100 times harder for you to convert. I think everybody will agree with that. The reality is maybe they did not. But the good side to it is the conversations were very good because we were able to ask them, why would you buy it and why do you think this is better? Why do you think this is solving your problem? We could get some hard responses for why we are building this solution. That was reassurance for us. And that support and that level of commitment at that point in time fuels you. It kind of drives you to build what you want to build. So that's a good side of it. Irrespective of what the conversion percentages are, you still should do it. But I'd say just don't rely on it 100% because it might not convert, but it's still good. You still should do it.

[Omer Khan]

Now, I want to make sure that I want to get specific enough that people understand what we're talking about here. So when you described a Netflix type experience, I'm not sure everyone would understand that. So why don't we just explain it in the context of sales enablement? And the typical scenario, if they're not using a product like Paper Flight, would be that sales folks are figuring out, okay, these are the customers I'm going to go and pitch to. These are the deck, the decks or the assets that I have to create to show them, to send them proposals. All of this stuff, as you mentioned, they're sharing it over Box or Dropbox or whatever, and they've got no idea if anybody is actually looking at this stuff. Right. And so describe, when you say that Netflix experience, describe how that is different for that sales team when they're using something like Paper Flight.

[Jaeger Kumaraptan]

The first problem here is easy access to content or easy access to knowledge. The first problem is making sure that you land all of the knowledge and content with your sales teams. That's the first problem. The second problem is for your sales teams to land that information with your buyers. If you talk about the first problem of landing with your sales teams when it's in folders, it's just not possible to figure out where's the most recent, most latest, what works, what does not work. But if I'm going to serve that to you in a Netflix like interface, if you work on a specific product in a specific region for a buyer segment, let's say enterprises, and you're selling product A and you're operating in the European region, I'm going to serve you content which is very specific to the product and the region and the industry that you're serving. And at the same time, this will also be content which is carrying a lot of telemetry around it in terms of what really works with a customer of this type, if the intent is of a certain order, what kind of content really works. So I'm able to, when you log in, you really see those, see all of those pieces of content, like, here's the new video on the product that you're working on. Here's what helped us close most of the revenue for this product in this region. Most successful sales reps use this content or this is what you should share at this point in time and in this deal stage. So that's landing with your sales with a field in itself. The second stage is for the sales reps to land this with, with your buyers, with your prospects. In most cases, like I said, it's an absolute blind spot for what really works and when do I share what kind of content? How long has it been since I interacted with the prospect? So based on all of this metadata, we're able to recommend, you know what, it's been a week and you are in the negotiation phase and you sent over material, which includes pricing. And in the last three days, I've seen your prospect interact with the pricing page, and multiple stakeholders in your prospect organization are interacting with the pricing page. Maybe this is the right time for you to reach out and talk about if you're concerned about this. Here's some discounts that we could offer, here's some tiered pricing models that could change how this could work. So we kind of establish it that they're interested in the product, but they're working on the pricing. So it gives you a lot of signals around what should your next conversation be about. So that's. Those are the two stages that we deal with from a. Primarily from a content and knowledge standpoint. Omer.

[Omer Khan]

Great, Great. Now, when you were going after the first 10 customers, the product was a lot more basic back then, obviously, that was like eight years ago. Walk me through what it took to close that first customer. Like, how did you find that first customer? You were obviously having conversations and getting feedback on the prototype, but how did you find that first customer, the one that paid, and how long did it take for you to close that deal?

[Jaeger Kumaraptan]

I'd say the first customer was still inbound. Or somebody who pinged us on intercom came through. They looked at the product. This was somebody who clearly knew what the problem was and exposed to what solutions exist in the market. Yes, our solution was kind of in its early stages, but someone who was willing to work with us to build this further as well. Now, in the first 10, one of the most interesting instances I could quote is one of those. One of the leads that came through voids was from S and P, the center in Flora. And this was an intercom ping. And we were too early and we really thought that somebody was playing a prank on us, like maybe one of our friends from somewhere or somebody within the team trying to reach out to us, asking. We are working on this conference called copy cop 22, and we need all of our research materials to be distributed at the conference. And we're looking for a product that does justice to all the work. And we were like, what really is? We didn't Even know what COP22 was. Later, it turned out to be the climate change conference. Very early stages. And again, for a brand like S and P to come through and for us to convert that. And we were the platform that was used to distribute the content for the. At the climate change conference for S and P. Kind of reassuring, pushed us forward to build a lot more.

[Omer Khan]

You know, before we started recording, I asked you about your GTM and you know, how you had grown the business to where it is today. And you said, it's all, it's all inbound. And I said, okay, great, what about getting to the first million? And you said, yeah, it was inbound. And I said, okay, what about the first 10 customers? And you said, inbound? And I was like, how is that even possible? Like, you know, most founders would build, you know, launch, they'd have a website, they'd be like, praying for any kind of SEO traffic and having like, you know, if they were lucky, having one or two people trickle in. So what, what did you guys do? What do you think you did differently?

[Jaeger Kumaraptan]

How?

[Omer Khan]

Why were these people finding you and reaching out through intercom?

[Jaeger Kumaraptan]

Very valid question. Just the website would not cut it for sure, especially when you're just starting off the ground. The first couple of years, we spent a lot of time on forums, on Quora, on Reddit, responding to questions, tagging the platform. This was the primary responsibility of a small team within the organization. So that way there was a lot of traction which we were able to identify. I'd say more qualified opportunities. And these are because when you get to a discussion forum and when you see a bunch of people discussing about a specific content problem or a distribution issue or any of that, these are very highly qualified leads. Now it's about how do we get to them and how do we engage with them. So the team would go after responding to all of these questions, connecting with them on LinkedIn, DMing them again. So we started running multiple threads around this, these smaller community of high quality leads is what I'd say, which kind of got us the first bunch of customers to work with us. And then the inbound engine got a lot more effective because you have a set of customers working with you already. And over a period of time, Google kicked in and we were able to snowball that whole path.

[Omer Khan]

Who was your ICP in those first couple of years?

[Jaeger Kumaraptan]

Head of marketing, cmos.

[Omer Khan]

Okay. And were you targeting a specific vertical or type of company or just anybody who was doing some kind of marketing?

[Jaeger Kumaraptan]

We did not. Interestingly, we did not at that point in time. We are now, but back then we did not also because we wanted to play it by how things move. So we were open to Start with, our focus was on the marketing industry as such, because marketing was more concerned about what's the ROI of my content, what revenue is it bringing, how much is my content influencing a deal? These were very important questions for them to have a seat at the table from a revenue standpoint. They were investing in in tools and products that will help them create the awareness for the products that these organizations are working on. So that was a sweet spot for us when we started.

[Omer Khan]

And then once you have that inbound lead, what does the process look like from that first contact to closing a deal? Is it like they go in through self serve and and sticking their credit card? Is it kind of more like a sales led process? What did you have to do? Let's talk about getting from zero to the first million. When you were closing those deals, what did that process look like?

[Jaeger Kumaraptan]

Early stages, again, self serve was harder because the product is also. Usually the product is also under evolution and you have customers who are going to come to you with newer requirements, feature sets that you might not have. This is the common problem that we see. So what we did was we worked with them. We wouldn't pass the ball on the other side and ask them start using the platform. We worked with them. We actually did a lot of heavy lifting also in those cases. So there's a lot of investment that goes from our end. Like for example, if you were to set up the whole repository, we work with them to figure out what are all the different content sources that you have today. You've got, let's say you've got some of your content on emails, on shared drives, in SharePoint or wherever it is. We pick all of that content, we work with them to clean them up, sort them, organize, tag them and then bring them into the platform. And they loved it because that's the investment from our end to understand how their businesses and processes work and work alongside them to make sure it is successful on both sides. And it's very important, especially when you're getting off the ground. Let's not look at it as a product that I've built. I'm just handing it over to you versus can I work with you to make this successful? Because that learning at that window of time is very crucial.

[Omer Khan]

Yeah, so you were providing a high touch onboarding experience for those customers, which makes a lot of sense and is probably lowers the risks when your product is still kind of evolving and you don't really know what about before that point, before they've reached out to you and they say we're interested and you haven't got as far as, yeah, they've given you money and you're onboarding them. What did that process look like? Would it be you would then do demos, you would then go back and do more demos, and then how long would it take before you would get to a point where they would actually close the deal and give you money?

[Jaeger Kumaraptan]

Very interesting question. So I was just thinking about how did we really do this is. For every prospect that reaches out to us, we would set up the entire platform very specific to that organization, because the team figures out what business are they in, what kind of content is already available over the Internet, how do they distribute it, how much of a sales team do they have, which regions do they sell to? We pick up all of them. This is a lot of work, by the way. I mean, it's not. It's unpaid work. Nobody's paying you for that. But when I build the entire Netflix like experience and on the demo call when we get in and when we show them, here's how your hub can look like, here's how all of your knowledge can look like. That's the first aha moment. That's actually when you tip them, that's actually when you. When the conversion happens. And from then on, it gets into subsequent questions about do you guys still do this? Can you offer this? Do you integrate with this platform? And I think those are. I mean, it was, it was easier to say yes back then. It is a lot more easier to say yes right now because building has become so simple.

[Omer Khan]

Were you doing that for the first 10 customers, like building these custom experiences for the demo, or is that something you do today?

[Jaeger Kumaraptan]

We still do. Depending on the size of engagement, depending on the brand that we are working with, we still do that. But I'd say up until the first 50 or 50 or 70 of those first set of enterprises that we onboarded, until that mark, we would do for every prospect. So that's. You can imagine, even if you do a 20% conversion rate, you're really looking at at 500, 600 prospect experiences or applications that the team would have built

[Omer Khan]

and how much time or man hours were going into preparing for each of these demos or experiences. Like, what was it like, a couple of hours I built something? Or this was like. No, it took days.

[Jaeger Kumaraptan]

It took like a day, maybe eight or 10 hours because there's so much of research work that you will have to do, pull all of it together. Setting up on the platform could be two hours, but there's at Least six, seven hours of work that you'll have to do before you consolidate everything.

[Omer Khan]

That is a lot of work for a demo call that you Basically, at a 20, there's an 80% chance they're not going to sign with you. And then to do that for like hundreds of customers. But what was the point where you guys said, no, this is working, we need to keep doing this. There must have been something must have happened in terms of closing a deal or a type of customer which gave you enough confidence to say, okay, this is a lot of work. This is a lot of time for every single demo call, but we need to keep doing because of this reason.

[Jaeger Kumaraptan]

I think in most cases it's the feedback, it's the excitement that we've seen, especially if we were able to do the first 10 customers, if we are able to convert them. And this is what has worked, I think that's the best lever we have from a product standpoint. But at the same time, Omer, we've run a B testing kind of stuff. We've kind of put this into two different sets of prospects and we evaluated what happens when, when we distance ourselves from the prospect and tell them that, you know, here's the product, go ahead and use it versus we work with them. It was, it was night and day. It was, it was just absolutely visible. From a data standpoint, the conversion rates were way less, and when I say way less, so the conversion rates were like some 2%, 3% on this side and 17 to 20% on the other side. So it was apparent. And so I think we should run these experiments. It's not like you figure it out and you just go on that path forever. Once you have to, at the right intervals, we run these experiments to see if we are on the right track.

[Omer Khan]

Got it.

[Jaeger Kumaraptan]

Okay.

[Omer Khan]

So basically you had the data to say, if we don't put this level of effort or if we put this level of effort into doing a demo, the chances are we're going to get a 20% or something around that ballpark conversion rate. And if we phone it in and do a very basic, deliver a very basic generic experience for the demo, the conversion rate is going to be significantly less.

[Jaeger Kumaraptan]

That is right.

[Omer Khan]

Yes.

[Jaeger Kumaraptan]

That's what we saw.

[Omer Khan]

Now, you guys raised, I think we mentioned earlier, like 400,000 as a seed round, and then you didn't raise any more money after that. Now, given where you guys are right now, you know, in terms of multiple seven figures in ARR, the playbook would be raise a series A right Go and you know, put some fuel on this, grow faster. You're in a, you're in a, you're playing in a space with some very big, very well funded competitors out there, right. So there's a lot of, you know, the TAM is, is, is pretty sizable and there's always an opportunity to even move more up market if you guys wanted to. So why, why did you decide not to raise any more money beyond the seed round?

[Jaeger Kumaraptan]

I'd say up until now we've, we, we had a trajectory and we, we, our growth was falling in line with the trajectory that we had and we had the Runway for it. We had the money to spend on what we wanted to spend on. So it was not a dire need to raise. But at the same time I think we'd always questioned about the good and the bad one end in terms of, in terms of scaling the product in the direction that you would like to. I'll give you an example of how Paperfly is a flagship product and at some point the industry was heading towards coaching and coaching was still stuck out in the age of where it was 20 years ago, where you have like slides that you would go through and at the end of it you will have a survey, questions and then you have a certificate at the end of it that was coaching. While as much as the industry was going after that, we wanted to look at content creation. So we went into the Canva kind of a mode where we wanted to build a completely different platform which would help you create content, interactive content, intelligent content, and then up until as early as two years ago when you had AI kicking in and there's a lot of LLM access coming in, which is when we decided that's the right time for us to get into coaching. Because as much as we disrupted the content space, this is the exact and also the content creation space and this is the right time for us to disrupt the coaching space. So we would build role plays and simulations and podcasts and micro learning and self learning and video bytes and all of that and tie that along the entire sales lifecycle. So there was, there were a lot of product directions and decisions that we could take and there was a lot of freedom for us to decide on how we'll operate, what we'll build and what we change rather than any kind of influence in those. And we love that freedom. At the same time, as long as it doesn't restrict from a commercial standpoint, from a capital standpoint, as long as we're not tight, we were fine. So that was the decision that we

[Omer Khan]

took, was there ever a point where you guys almost decided, okay, let's go out and do, you know, try to raise another round? And then you sort of pulled back?

[Jaeger Kumaraptan]

Not really. I mean, we've had interest for investments we did pursue for a little while and then we figured out. And then we pulled back as figured out. Maybe not, maybe not now, maybe, maybe when you build the next product, maybe the next product of sorts. But I don't think it has constrained us in any form. But I do agree that moving forward, because distribution muscle is the key, because building as much as we've built so much, as much as we have an understanding of the depth of how this industry operates, as much as we have all of that distribution has become key. And we are working to see how, how do we build on that muscle? That is something that we've been thinking of now. Yes.

[Omer Khan]

Yeah. I mean, essentially I think what I'm hearing is you can look at this business and you guys raise the seed round and the playbook might be to go and raise the Series A or whatever, but fundamentally you guys are more like bootstrappers and you like having that freedom to, to build the kind of product and business that you want with as little interference as possible and go as far as you can down that road.

[Jaeger Kumaraptan]

True, true. But again, I do agree that times are changing and then we still have to look at distribution. The challenges evolve, but until now it's not been a critical factor.

[Omer Khan]

Tell me about competitors, how you guys think about that in the space. Obviously the biggest players in the market, like the seismic and recently there were the seismic high spot merger, it's kind of pretty massive, I don't know, billions of dollar type kind of merger. How do you guys see yourself fitting in that market? What's the kind of niche that you've carved out for yourself? And how much time do you spend looking at some of those bigger companies?

[Jaeger Kumaraptan]

A lot of time off late. Earlier we felt, let's say eight years back or five, six years back when we started, when we were working with small, medium customers. Seismic and high spot would always look at, I mean we would always look at them as, you know, a little too far off, far fetched for us. But what's happened in the last couple of years is we've converted quite a bit of seismic users and ispot users into pay per flight. So it kind of gave us the confidence as to the journey that we've come through. I mean it was never a question of features or capabilities because we were always on par. We were really competing but at the same time the way we solved the features. I'm sorry, the way we solved these problems were very creative, innovative and also based on the very technology heavy. And in that case we were always ahead of all the names that you just mentioned. But purely from a distribution muscle and from positioning standpoint, the market would still look at sitelink and high spot from sites of engagement that they work with. But considering what's happened in the recent the way I'd say is the consolidation. Again, there's so much of consolidation that's happening in the market, especially this one between high spot and seismic is key is crucial because we were looking at converting either from a high spot or a seismic and now that they're together it's good and bad. One is the fact that consolidation helps. The market is coming together as a much stronger product. And also for us it's one brand to, to. To look up to, to follow and to and to be the next best to start with at this point in time. Kind of clears the air for us, gives us a really good sweet spot for us to position ourselves. That's how I look at the.

[Omer Khan]

The consolidation and what's the bad bias side of it?

[Jaeger Kumaraptan]

The bad side of it is it's not about the consolidation. The bad side of it is what's happening on the. On the opposite side. On the flip side, which is there's a lot of pointed AI solutions that are coming up which solve a very specific problem with I mean I'd say generic because they're very new in the market, but they want to solve one specific problem. Let's say you want to solve role plays, only role plays or you'd like to only create a deal room and then manage just the deal room. Or I have an Outlook plugin that kind of helps you fetch content depending on what email you're writing. So you have all of these pointed solutions and the market is really cluttered which is the other side Kind of there's a lot of noise is what I'd say but that clarity has to. It's going to take some time for that ad to clear off for us to really see who's able to sustain who's not able to or how do they grow their roots is something that we are yet to see.

[Omer Khan]

Yeah. Okay. So on the one side you've got these big players like seismic HighSpot. On the other side you've got a lot of these new AI first entrants and you guys obviously weren't an AI company When you started eight years ago, but you've rebuilt a lot of the product and become AI is much more a native integrated part of what you do today. But how do you think about your positioning? For example, you mentioned, hey, we have, from a product perspective we're on par. We have features, maybe some that are better than what these big players are doing, but we don't have necessarily the distribution, the mindshare, et cetera. Right. Which is super important because these days building a product has become so much easier. And even if you build an amazing feature that doesn't necessarily mean anything, which is the same thing with vibe coding, you can go and build an amazing product that does what I don't know, I don't even know what seismic features are, but does a whole bunch of stuff that seismic does. But you don't have any distribution. So just tell me about how do you guys think about navigating that and what do you think is the most important differentiator? Like if you're talking to a customer, why, and they ask you why should I pick paper flight versus you know, these, all these other things that I have available in the market, what would

[Jaeger Kumaraptan]

you say you need a combination of both. You need somebody who's had the, the industry experience but not too old to, for it to be difficult to change. You need for example the products that I talked about, let's say content creation or content management or, or the coaching. The coaching part of it is, is 100% AI native. The content management part is 50% AI native and the content creation is like 70% AI native. So that' products have actually evolved now this is, it's. I'd really say it's a sweet spot or the best blend of expertise and experience in the industry and the advancement from a technology standpoint and the capability to move faster forward. So if I look at the two sides in between, like to my left, I have the white coded platforms that are entirely new and I don't know if they will be able to scale. The problem is from a security standpoint, from a scale standpoint, from data management, from concurrency, and these are areas where even maintenance is a big problem. And what I'm hearing is also that when we talk about pure play AI revenue, that's a challenge. We're still not able to see a credible dollar figure out there for, for the wife coded platforms yet. And on the other hand you have larger massive organizations. Again, How flexible are they? How fast or how swift are they? How swift can they move? Can they change? Can they re Architect. It is going to be harder. I mean it's going to be hard to, to move a truck versus a bicycle. So it's kind of, it is harder on the other side. Now you have, you're somewhere in the, in the sweet spot where you've got the experience. You've built this for the industry for a good number of years, but at the same time the team is also moving forward really fast and you're ahead of the curve when it comes to technology. It's a nimble team that can help you adapt everything faster. So your organization, the buyer, buyer's organization can and grow faster and you will be ahead of your peers. That's what we have seen. They are ahead of their peers in the industries that they operate in. So that is our sweet spot. That is our strength.

[Omer Khan]

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All right, we should wrap up, so let's get on to the lightning round. I've got five quick fire questions for you. You ready?

[Jaeger Kumaraptan]

Yes.

[Omer Khan]

Okay. What's a common piece of startup Advice that you disagree with.

[Jaeger Kumaraptan]

You build a product, meaning you build a really good product and you watch and the product will make the sale. Or that's going to help you just do everything? I don't think so. You've got to have an amazing team. You got to have a structured approach, and you need to know what. You need to have a plan for what you've got to do.

[Omer Khan]

What is a recent great book that you read?

[Jaeger Kumaraptan]

Not really a book per se, but this is an essay, Dario Amodei's essay on Machines of Loving Grace. I think that was really insightful. It brought out the human side of AI and how AI would really be put to use, rather than everything that we see in the news right now. I felt it was really deep.

[Omer Khan]

Cool. What is something that you have had to learn the hard way as a founder?

[Jaeger Kumaraptan]

Again, products. When we roll this out, it's very difficult for you to split the view between how you look at the product versus how your users look at the product. We've always built it when we know this is a solution, this is how it's going to work. And in most cases, or rather in times where we have not watched out for how whatever we built is being used, we've lost time, we've lost revenue, we've lost time. So it's not just about how you look at it. The harder thing is that for you continue looking at how the users perceive whatever you've built or how the problem is actually being solved on the ground.

[Omer Khan]

What's a tool or habit that saves you the most time?

[Jaeger Kumaraptan]

Notion. I've got a lot of notion boards.

[Omer Khan]

And finally, what do you do for fun when you're not working?

[Jaeger Kumaraptan]

I run. I love good design. I want tracks. That's what I do.

[Omer Khan]

Cool. Well, Jaeger, thank you so much for joining me. It's been a pleasure. If people want to check out Paperflight, they can go to paperflight.com. that's F L I T E dot com. And if folks want to get in touch with you, what's the best way for them to do that?

[Jaeger Kumaraptan]

LinkedIn. I'm quite responsible on LinkedIn.

[Omer Khan]

Awesome. We'll include a link in the show notes. Thanks, man. And I wish you and the team the best of success.

[Jaeger Kumaraptan]

Thank you so much. It was really nice talking to you. Same here.

[Omer Khan]

Cheers.