How Loopio Won Its First SaaS Customers With Beta Interviews

Omer (00:10.000)
Welcome to another episode of the SaaS Podcast.
I'm your host Omer Khan and this is the show where I interview proven founders and industry experts who share their stories, strategies and insights to help you build, launch and grow your SaaS business.
In this episode I talk to Jafar Owenotti, co founder and COO of Lupio, a SaaS product that helps enterprises to streamline the way they respond to a request for proposal or rfp.
This episode is a story about three co founders who were all first time entrepreneurs.
One of them was working at a company as a sales engineer and spent half his time responding to RFPs.
He he realized he was getting asked the same questions over and over again.
Being an engineer, he decided that software could streamline that process and started building a product in his spare time.
But the idea went nowhere and his software just ended up collecting dust.
Sometime later, the founders got together and came up with a new plan.
Two of them would keep working full time jobs and work on their product in their evenings and weekends.
And the third founder, Jafar, quit his job to work on the business full time.
There were already products that helped Companies respond to RFPs, but the founders believed there was an opportunity to modernize that with a SaaS offering.
Jafar spent a lot of time getting introductions, interviewing potential customers, getting feedback on their product demo, and basically learning how they could help companies to respond to RFPs more effectively.
A lot of those meetings were a waste of time and at that point the founders didn't have a clue on who their ideal customer was.
They were just open to talking to anyone who would give them time.
Eventually, that hard work paid off.
They were able to build a good enough product even though it lacked a lot of features and win some early customers.
They bootstrapped the business for the first four years before raising a $9 million Series A round in 2018.
Today they have a team of 140 people and are doing eight figures in annual recurring revenue.
In this interview you'll learn some great lessons.
We explore how the founders figured out who their target customers were, what they learned about interviewing prospective customers, how they came up with their pricing, and how they learned to sell a SaaS to enterprise customers.
So I hope you enjoy it.
Jafar, welcome to the show.

Jafar Owainati (02:41.170)
Thanks Omar.
Thanks for having me.

Omer (02:43.410)
So I always like to ask my guests if they have a quote or something that inspires or motivates them or gets them out of bed.
Is there something you can share with us or just tell us in your own words?

Jafar Owainati (02:53.730)
For sure.
I'm not Much of a quote person, but there's really important to always have a point of motivation that gets you up and excited to do what you do every single day.
For me, I break it down into two main areas.
One of the main things for me is building an organization in a company where everyone who comes to work is really excited to be there and is growing and learning.
And really, Lupio being the place where our team members are able to look at as a bright spot in their careers and basically as a launching pad as well.
The second part for me is on the customer side, and I get really motivated and excited when I know that what we're doing is driving impact to our customers and usually translates in that email that you get or the nice conversation you might have over the phone, or even what someone might leave as a review.
Those are the things that really get me excited and really drive me to do what I do every single day.

Omer (03:53.749)
Okay, so tell us a little bit about Lupio.
What does the product do, who is it for, and what's the main problem you're helping to solve?

Jafar Owainati (04:04.370)
For sure, if you've ever responded to a request for a proposal, a vendor assessment, a security questionnaire, you might know that it's a pretty painful process in terms of collaborating and finding the right content to respond to those requests.
And so Lupio is an RFP response platform that helps businesses supercharge their response process for these types of documents.
And our platform's unique approach to content management, collaboration, and our intelligent automation features let teams quickly craft winning responses with less effort.
In terms of who we cater to, our customers go across many different industry verticals, but we work really closely with organizations in technology, software, financial services, insurance, health benefits, and cybersecurity teams as well.

Omer (04:57.860)
Okay, so the company was founded in 2014 with your co founders, Matt and Zach.
Tell me about how you guys came up with the idea for this business.

Jafar Owainati (05:11.130)
Well, the idea goes back to probably around 2010 or so.
Zach, who is our CEO, is the person who explicitly felt this pain.
Point of responding to RFPs.
He worked at a.
At an organization based out of here in Toronto that focuses on employee rewards and recognition.
So they were a SaaS company selling to really large organizations, and he took on the role of being their first sales engineer.
And he's basically, you know, the technical backbone of the sales team, supporting in things like proof of concepts, answering questions around integrations, and configuration.
But then he very quickly saw that probably half of his job was answering these different RFPs and requests that would come up in the sales cycle and recognizing that a lot of the same questions keep getting asked over and over again.
And that's where really the idea came together.
There's always been solutions in the market that cater to the specific pain point, even back then in 2010 and 2012.
But there was really an opportunity to modernize that process and really bring it into sort of newer web technology.
And that's where Lupio came together.
It did take a few years from sort of idea to us coming together as a team to build the platform.
And we launched the business in 2014.

Omer (06:37.270)
Okay, good.
So I want to kind of dig into that and exactly what you guys did to turn that idea into a product and how you found your first few customers.
So before we do that, let's give people a sense of the size of the business today.
So tell us, in terms of like revenue, size of team, where is the business at today?

Jafar Owainati (07:00.850)
From a recurring revenue standpoint, we're in the eight figure range from an ARR standpoint.
And in terms of the team, we are about 140 people, all based out of Toronto, Ontario.

Omer (07:14.450)
And in terms of funding, you guys have raised around $9 million, correct?

Jafar Owainati (07:21.230)
Yeah.
So we're a Canadian company.
We raised US$9 million in late 2017, and that's the only round of institutional capital that we've ever raised.
We were a purely bootstrap company for the first few years of of our business.

Omer (07:39.470)
Yeah, I think from when you and I chatted, I think it was about four years that you guys bootstrapped the business.
So I really want to dig into those four years and see what we can learn from, you know, your experience of taking an idea to market and building a product.
So let's kind of go back, as you sort of explained, like Zach.
So this opportunity from personal experience, how did you guys get started?
Was this about.
We're going to go and start to talk to potential customers.
We're going to build an mvp.
What did you do?

Jafar Owainati (08:16.770)
Yeah, I think it starts off first and foremost with who the team is and what our capabilities are as a founding team.
So I lean more towards the business side.
But Zach and Matt are both computer engineers by training, and they're both software developers.
Both of them were more senior in their careers at this stage when we were starting the company, but also still very much capable of building software.
And so I think that's a really important note when you think about starting a technology company is when two of three members of the team are able to actually build the product itself.
I think that's a really powerful thing, especially when you're thinking about funding and being able to go to market with a solution.
So Zach and Matt were really going full force in building the first version of the product.
The other part of it, when we think about starting a business, especially when it's a number of co founders, is who's taking the leap of faith, who's starting when and how do you think about really going all in as a team?
And we did it in stages, so I was the first person to really go all in and work full time on this.
And Zach and Matt were still taking on full time roles at full capacity, but we were all spending evenings and weekends working together, and they were basically coding at night and on the weekends.
So what that meant was, for me, being full time, most of the early stages were focused on business development and really digging in and exploring the problem and understanding how to build a solution that caters to the biggest spikes in pain in the process.
So that the MVP was really solving those really, really big problems versus, you know, trying to solve for everything in terms of the business development process and finding those first customers.
I spent a lot of time leaning on my network first to get introduced to people with the purpose of really learning and leaning on those individuals as experts on how we can solve this problem of responding to RFPs effectively.
And what that translated to was asking the question of their interest in participating in a beta, but also asking the question if they knew anyone else who we can talk to.
And that sort of created a domino effect of getting introduced to more and more people.
And eventually we leaned into launching a private beta that we also put a bit of advertising dollars towards through just having a landing page and getting some signups that way.

Omer (10:55.330)
Okay, how long did it take you to get to a point where you were able to launch the private beta?

Jafar Owainati (10:59.570)
It was a matter of a few months, probably four to five months.
I should note that some of the initial building blocks of the platform started happening sort of earlier on when Zach first came up with the idea, but that basically it collected dust for a while before all three of us came together.
So there were some foundations already built in in terms of the product, and there were some early progress.
But from us deciding to come together and build what we now call Lupio, I would say it was only a few months before we had a beta ready to go.

Omer (11:35.330)
Okay, and so before you sort of, you know, went in full time and Zach initially built this product, where were those requirements coming from?
Was it just based on his own personal experience?
And what he felt this product should be able to do.

Jafar Owainati (11:49.930)
I think the, in terms of the ideation portion of just conceptually, it did start with Zach's experience, but in terms of what we were building into the beta, we leaned really heavily on the early customer research that we were conducting.
So walking through the pain points of a few different interviews and basically ideal customers that we would want to be targeting, and then really digging into their process to understand what an early version would look like.
And then during the beta, just digging in, asking questions, exploring.
So, like real customer development as it came to evolving the product.
So we didn't want to lean too heavily on, like, this is Zach's experience, and we're going to build just to serve what Zach perceives as being the right things to solve for.
We really tried to get a diversity of input and we built a comprehensive interview guide on how we did our user research in those early days.

Omer (12:48.130)
Okay, so when you were trying to get these introductions and find people to talk to, firstly, how did you figure out who that target customer was?
Like, did you have a specific segment in mind or was it kind of pretty broad at that point?
In terms of anybody who might be dealing with RFPs, we had an early

Jafar Owainati (13:17.860)
hypothesis in how we were thinking about the problem that we're solving.
When you think about an rfp, a request for proposal, at the end of the day, the response to that is a business proposal in its own right.
And some organizations may be responding to RFPs for services that are highly, highly customized.
So if you're dealing with some form of a professional services that's responding to a really large, very tailored type of rfp, there may not be a lot of content that's being developed that is repeatable content.
So one of the big things that we talked about it was around what is the value that we're driving.
And one of the core values that we decided we were driving forward is around efficiency and automation.
And to drive automation, there needs to be repeatability.
So we started off with focusing on organizations by the nature of their products and how they go to market, that they would have a very repeatable content.
And some of those types of organizations, and part of that comes from Zach's experience as well, are software companies.
Software companies sell a subset of products.
Sometimes it's one product, sometimes it's a suite.
But if they're responding to an rfp, it would be very typical that there would be overlap in content.
And so that was a critical criteria on how we're thinking about the markets that we were targeting.
That does apply to other markets I mentioned earlier, financial services, insurance, cybersecurity.
It is relatively broad.
And I think what's really cool about the market that we tailor towards is that it is quite horizontal.
We are vertical agnostic, although that there are some verticals that we do better than others.

Omer (15:04.580)
So tell me a little bit about these, these interviews that you did in the early days, because I think that's it's not the sexiest thing to be doing, but it's so important.
And a lot of founders in the early stages, number one, either have a hard time if they figured out who that target customer is, they have a hard time getting those people to pay attention and, you know, give them time to have that type of conversation.
And secondly, they're often kind of struggle with like, how do I use that time?
And.
And sometimes they're sort of a little bit too far ahead in terms of thinking.
Well, they're sort of really thinking about it as this is my opportunity to go and sort of tell them about my product and my idea and how it's going to make the world better.
But I think from what you've already said, it sounds like, number one, you will focus much more in terms of figuring out how they were doing things and what problems they were having rather than talking about your solution.
Tell me about your experience there.
And I want to sort of figure out if there's some lessons that you learned going through that process that we can share some wisdom with people listening.

Jafar Owainati (16:10.890)
For sure.
I think part of the experience on doing those early, call them beta customer interviews, I definitely leaned a little bit on my previous experience before starting Lupio in management consulting, where a part of my role and certain engagements I worked on involved getting in touch with people and learning from them.
And those people that I was tasked to get in touch with were people that you would usually expect that they wouldn't want to talk to anyone or share any information.
And the big lesson that I learned early on was that people who spend their entire day at work and who build their expertise in a certain space, they love the opportunity to be able to speak of their work and to be leaned on as experts because they worked so hard to get to where they are.
And that's the number one point of framing that we've always had in these kinds of conversations are we are building a software company.
We are not experts in the space, but we are experts in how to build software.
The experts are the customers or the prospects that we're talking to.
And we want to Learn from them.
And to your point, the big thing that we did was in those beta interviews, one of the things that we have on the top of that interview guide was basically a mandate.
And the mandate included the fact that this was not a sales conversation.
And so reminding yourself of that before every dialogue is super important.
And to really have the objective of really leaning in on the experts that you're talking to, being extremely curious, making your interview guide adaptable, and that you're not just feeling like you're going through a checklist, that you're really navigating and trying to dig in into those areas where your curiosity starts to peak.
And the big question that I always ask at the very end is, is there anyone else I can talk to?
Would you be open to continuing the dialogue?
And you're basically opening up that conversation where you can then when you do have a product or you have something that's going to drive value and solve their pains, specifically in how they describe the pain to you, then they're going to be interested in wanting to engage and potentially purchase.
A number of those beta interviews translated into customers.
And I will say specifically for a few of them, they're, you know, six years in, they're still customers.
And some of those organizations got acquired by other companies.
One got acquired by IBM and now we're growing across IBM more globally.
Like it was from those early discussions.
Like, it's really amazing the relationships that you can build from being genuinely curious and wanting to solve the pain points that someone's going through.
I don't know if that answers your question, but hopefully that's helpful.

Omer (18:57.280)
Yeah, yeah, it is.
And I think it's like, number one, I think for me the takeaway was, you know, remind yourself as well as make it clear to people that you want to go and talk to that you're not having a sales conversation.
It's not about your product, your solution.
It's about them and what they do, their business, their problems.
Secondly, I think there's a lot of value in being able to, you know, position yourself as somebody who's learning and they're the expert that, as you said, you know, number one, people like that.
And two, I think it's.
It's.
People become a little less, maybe defensive.
They're kind of more willing to talk when they feel like that.
And then I think it's gold in terms of, you know, at the end asking if there's anybody else that you can talk to.
Because one, yeah, great.
That's, you know, the more you can get These conversations through introductions, the more likely those people are going to be to say yes and be willing to meet with you.
And also in many ways, I think if at the end of the conversation, you know, you're not having a sales conversation, but if somebody is able or willing to feel good enough at the end of a conversation to refer you or introduce you to somebody else, then that in itself is a good sign that you're headed in the right direction.
Right.
That, number one, you did a good job in terms of having that conversation.
They didn't feel like you were some douchebag trying to sell them stuff.
And secondly, it's kind of a way of them making that first commitment.
Right.
In terms of, yeah, I'm kind of okay with my reputation and kind of referring you to somebody else.
Yeah.

Jafar Owainati (20:42.400)
I think the key point, especially in the early days, it's not about the money.
It's not about closing the deal.
It's about showing the other party that you hear their pain and the reason why you're building your business is that you want to solve the problem for them.
If you're focusing on solving the problem first, the money will come.

Omer (21:02.090)
So let's talk about.
So you did the closed beta.
How long did that go on for?
Were there any major lessons or insights that you got that sort of forced you guys to change direction in any way, or was that a good validation that you were headed in the right direction and you just kept going?

Jafar Owainati (21:20.730)
The beta was, I believe, about four months long.
I thought that it was a good exercise to go through as a way to get really direct feedback of people using the product itself.
I think about some of the challenges of a free beta is that one, it's free.
And so what that means is that the other party doesn't necessarily have skin in the game.
So you're going to have a diversity of engagements in a beta.
And we definitely had a subset of users who would go in from time to time and they would share some feedback here and there, some that barely even use the product and others who were hopping on calls on a regular basis and were just so excited to be part of the beta.
So important to acknowledge that as part of a free beta.
I think back then as well, and also perhaps being a bootstrap company, you know, we didn't necessarily invest in tooling around the beta to be able to monitor engagement and see how people were doing things from a user testing standpoint.
And I know there's a lot more technology around that as exists today.
It was really around qualitative feedback and getting on the phone.
I think the big thing for us was deciding when we felt the product was mature enough to start charging.
And I will say that you never feel like the product is mature enough.
And we just made a call at one point and we were just like, you know what?
We're ready to start selling.
And we literally just flipped a switch.
We did a transition period for the beta customers to say, the beta is going to expire at this date and if you want to move forward, you're going to get preferred beta customer pricing.
And then we just started demoing with the purpose of closing deals, and we never looked back.

Omer (23:07.840)
What was the reason that you didn't charge people right away?
I mean, it's something that, you know, we hear a lot with with new founders.
And, you know, you should start charging as soon as possible to figure out whether you've actually got something that people are willing to pay for.
And even if you're not charging the full price, even getting people to pay anything is a good thing.
And I think, as you alluded to, when you're giving away the product for free, it's not always easy to figure out, are these the right customers?
If we started charging, would they pay?
And it was also hard to kind of prioritize, I guess, the feedback that you get.
I mean, quite often when you have a free product or a freemium model, it's often the people who don't pay you who seem to be the most vocal with the features that they think you should have in there, and they're often the people who never buy your product.
So what was the thinking for you guys and why did you decide not to charge for the beta?

Jafar Owainati (24:16.560)
Yeah, I think for us in terms of the beta, the product was missing some really, really core functionality.
But we wanted to get it in the hands of people and just to be able to engage in more conversations.
So I do think that relative to other sort of technology companies, we were relatively quick in flipping the switch and charging for the product.
I do think it's important to consider as well of who the user you're engaging with and who the buyer is and what kind of software company you're building.
Like for Lupio, when we first started the business, we really entered into the assumption of this was going to be a monthly subscription business where people would put their subscription on a credit card, and it was a relatively small, average deal size.
What's interesting is we very quickly realized just how much more of a enterprise grade solution we would need to be.
And how much this catered towards larger organizations as well and that we wouldn't be a monthly on a credit card kind of company.
And that was communicated to us not necessarily as a.
By us making a call.
It was, we charged monthly but then we offered at the time a discount if you wanted to go annually instead.
And what we saw was almost everybody opted to the annual option which was great for us to help sustain as a bootstrap company because we're collecting cash up front.
But we relatively quickly shifted our model to be more focused on annual subscriptions similar to a Salesforce and other sales focused software would be doing as well.
So that was a big shift for us.
And then our pricing continued to grow and evolve very quickly.
One piece of advice that I had someone share with me which was really impacted us in the early days I was talking about how we're doing in the market and competitively and they asked the question of have you ever lost a deal because of your price?
And at the time I was like I don't think so, no.
And then he was like cool, keep increasing your price until you do.

Omer (26:28.740)
Yep.

Jafar Owainati (26:29.700)
And that was really helpful advice because in a market where you don't necessarily have the comparators in terms of what other solutions may be charging, whether that's because there aren't other competitors, which is unlikely I would say in the world that we operate in today, or it's because perhaps your competitors do not have price transparency so you don't have an indication of what that would be.
But then you also going to lean on willingness to pay.
At the end of the day it's what is the value you can generate in your solution and how much can you capture of that value in the form of what you're charging.
And a way we were able to identify that is by pushing price up over time and seeing how the market reacted.

Omer (27:15.220)
So when you first started charging, how did you figure out that price?

Jafar Owainati (27:20.820)
It was more art than science, you guessed?
Yes, we gave it a shot.
We looked at other software that serves.
Basically we sell into sales teams at the end of the day.
Yes.
We have proposal managers, RFP managers, sometimes it's solutions consultants or sales engineers who are buying, but they're also the same end buyers who are buying things like Salesforce.
You know, at that time Salesloft and Outreach were relatively new products in the market from a email cadence perspective.
But we always have to think about what is in their sales stack and how does our product compare to the other technologies that they would be using in their sales Stack?

Omer (28:05.930)
Yeah.
Yeah.
I mean, it's pretty easy to get hung up on the price when you're starting out in terms of I gotta figure out the perfect price.
But, you know, I think the lesson here is like, it doesn't really matter that much with those early customers as long as you're.
You're gonna continue to optimize and test different pricing until you figure out what the right, you know, thing is.
So I'm curious, like, how did you start to increase the price?
Were you, you know, pretty transparent?
Was there, you know, a pricing page on your website and you just kept changing that, or was this more about, you know, we don't talk about the pricing on the site, but when we have that sales conversation, that's when we talk about the price.
And you were testing sort of different price points there?

Jafar Owainati (28:47.820)
Yeah, I would say in the early days, we had no price transparency in terms of the website.
Even today, if you go on our website, we have a plans page, but it doesn't explicitly mention the pricing for each package.
With that said, we really believe in price transparency and consistency.
So when we have that sales conversation, we are very upfront in terms of this is how our pricing model works, this is how it's structured, this is the pricing of the different plans.
But it's always important that we position the plan that makes most sense for the organization that we're talking to.
So we do think about positioning of our pricing plans accordingly to the right people so that we're having the right dialogue and getting the buy in accordingly.
In terms of the early days and how we were looking at pricing, so we didn't have pricing on our website.
None of our competitors did either.
And I would say that none of our competitors have that today.
So it's also important to note, like, what are the market expectations in the market that you play in?
If all of your competitors have a pricing page and have all their pricing on there, you have to also do the same thing.
You can't be the odd person out because it's not going to communicate or send the right message to the market.
And so in terms of flexibility, we always set our pricing and kept it as consistent.
We didn't.
A B test within the people we were talking to is once we made a decision on our pricing model and our pricing plans, that's what it was.
And then if we change them, we change them holistically moving forward.
They.
The important note that we're really sensitive to, especially in the early days, is what is the impact on your customer base There are some organizations that philosophically believe that all customers need to be on the same pricing plan, and so they'll move old customers into a new plan.
The challenge becomes if the new plan will fundamentally shift how much they're paying, whether it's up or down.
There needs to be considerations on the business risk associated with that and also on the customer relationship side as well.
So we've been really thoughtful on how we go back to our existing customer base, especially in the early days.
In the early days, we grandfathered every early customer, so we never shook things up in terms of the base, especially when your base is small relative to where you're going as a business.
So in the early days you have much more flexibility in what you want to do.
Because if you want to grandfather your early customers, they took a leap of faith to work with you and take on your solution, and they put themselves at risk by sort of putting their hand up and standing up for you and buying them within their organizations.
So you should give them something in exchange for that by keeping them on legacy pricing.
So those are some of the considerations.

Omer (31:38.130)
Yeah, it's an interesting debate there.
Right.
In terms of grandfathering or not to grandfather.
And I've heard sort of an equal case in terms of why you shouldn't grandfather people.
But that's probably a conversation for another day.
I want to talk about growth, and it sounds like a lot of these early customers came from you going out, getting these introductions, talking to customers, and then eventually going back to them to talk about the product.
You also used a couple of paid channels as well to help drive growth.
So I want to talk about those.
So one of those was Capterra, right?

Jafar Owainati (32:25.240)
That's right.

Omer (32:26.600)
So how are you using that and what sort of results did you get?
And maybe before we even get into that, maybe we should just.
I think most people are familiar with Captira, but we should.
If not, we should probably just explain what that is.

Jafar Owainati (32:39.930)
Yeah, I'll provide, I'll provide some background on it and how that worked for us in the early days.
I think also really important to note in that in the early days, the targets that you're setting and what you're trying to capture from a market standpoint is much smaller than as you continue to grow and evolve as a business.
So as we look at channels on how we acquire customers today as a company with 140 people with over 800 customers, it's very different than back then.
But I think the early days are really, really important to consider.
And so to the Point on Capterra.
Capterra is a business to business software comparison website.
They categorize different software solutions into different groupings.
They just so happen to have one that was called proposal software, RFP software, which is exactly where we fit in.
So when you think about the early days of building your business, some of the things that you think about is how do I rank organically for the terms that people are going to search for so that they find us?
And we are on the top of sort of the Google Page rankings.
So as an early business and building out our content and building our website, Loopio was not on page one.
I think we.
Obviously it takes time to build your search engine optimization to get to that point.
But if you search for proposal software, Capterra for our category was showing up as the number one ranked search every single time.
And so what we identified as an opportunity is to advertise on Capterra specifically.
So you would search proposal software, you would click on Capterra because it was the number one link that said, click, click here to see the top solutions.
And we were paying to be prioritized or sponsored on the top portion of that list on proposal software.
So the key there is being above the fold.
And we actually ended up converting and bringing a lot of opportunities in through that channel in the early days.
And, you know, I guess we will forever be grateful to Capterra on how much it's fed our business in those infancy days of the company.

Omer (34:59.170)
The folks at Capterra and Gartner, I guess, will be very happy to hear that.

Jafar Owainati (35:03.730)
Yeah, I will say it's not working as well as it used to, but the needs have changed as well.
And the volume that we focus on driving is substantially higher than what it was back when we were a business made up of just me, Zach and Matt.
It was just three of us for a long time.

Omer (35:21.030)
Yeah.
So I know that Capterra these days has kind of like a pay per click model where if you're in that sort of, let's say you're in that proposal RFP category.
If you go and submit, you can get listed there organically and you might show up, you know, the 57th result on the list or something, or you can bid and say, you know, I'm willing to pay just like you would with Google AdWords and then you can have the opportunity to get featured, you know, at the top of the page.
Was that the same model that they were using when you were using them when you started out using Capterra?

Jafar Owainati (36:01.820)
It was so if you didn't pay, the number of reviews and your review ranking in terms of how positive your reviews were would also impact where you would rank.
So we also did lean quite heavily on customer advocacy to drive reviews and get Lupio, sort of, even if it was organic that we would be higher up on that page.
But we definitely paid per click.
And that was the model back then.
I believe it's still the model today to be prioritized.
I would say the cost per click in our category back when we first entered the market was relatively cheap, and that's where it was a very efficient channel for us to even drive beta customers before we were charging.
It is substantially higher today on a per click standpoint, right?

Omer (36:51.540)
Yeah.
And that's a good lesson in why you should be looking at marketing acquisition channels that your competitors aren't currently using today.
And while they might not be massive and obvious as saying, let's go and use AdWords or LinkedIn ads or something like that, there may be these kinds of opportunities out there that you can, you know, get.
Get a decent, you know, ROI on, on your spend.
And yeah, if you go in Capterra and you're paying, you know, $10 a click versus, you know, you know, a few hundred dollars, it's a very different, you know, model there.

Jafar Owainati (37:30.910)
And it all depends on how much volume you're looking to drive from a lead and opportunity standpoint.
And so in the early days, you're basically like, every single opportunity counts and you want to talk to almost every single person.
You need to be thoughtful on who you're engaging with and how you're qualifying.
But to your point, on channels, there may be some channels that are really cost efficient, but they're cost efficient at low volumes, and they could plateau relatively quickly.
But that's okay.
It's better to be the big fish in a small pond.
And that's how I think about marketing channels in the early days.
Be the big fish in the small pond.
So for us, that was Capterra and drive those early engaging opportunities.
And then as you start building out your entire digital marketing strategy and your demand generation strategy is when you can start thinking about the broader, more expensive spend.
As you look at Google, LinkedIn, Facebook may be relevant to your business, or Instagram may be relevant to your business as well.
And then just keep analyzing those channels and how you're converting and what your cost is per opportunity.

Omer (38:38.550)
And you were also using AdWords.
Was that around the same time as when you started using capterra?

Jafar Owainati (38:46.950)
Yeah, Google AdWords, we were using not as extensively and I would say with a lower level of maturity because it is much more complex in how you think about managing your Google AdWords campaigns.
We started off with just, you know, standard Google search ads that you'd get if you're just searching on Google more on a regular basis.
And eventually it evolved into things like retargeting and using different channels as well as associated with Google Ads.
But we started very narrow with Google and then went more broad over time.

Omer (39:26.330)
So one of the things I liked that when you and I had chatted earlier was that you kept it really simple and often we sort of have this tendency to sort of over complicate things.
And it's kind of cool to build funnels and sales funnels these days.
But as I recall, your adwords were just pointing what to a calendar link that people, people could book a demo with you.

Jafar Owainati (39:52.980)
So it still did hit a landing page.
The key thing was the call to action that was on our website.
So, you know, if you go on many B2B software websites, some of the main calls to action that you might see would include something like request a demo or talk to us and our request demo button.
So traditionally what you'd see when someone clicks on that is you would go into a form to fill out things like your contact info and an inbound sales development rep might sort of reach back out and qualify.
And if it is qualified, then you would book a demo.
The early days for us was all about let us remove as much friction as possible.
And the request demo button, to your point, linked directly to my personal calendar.
We used Calendly back then and this was in 2014.
So it was the early days of Calendly and now Calendly is a, you know, I would consider to be a very successful SaaS solution that drives calendar management and appointment booking.
Funny enough, they also got invested by our same investors as well.
So we're now sort of sister portfolio companies.
But yes, we used Calendly and it linked to my Google Calendar and people would just book demos and, and there was a point in time I was doing seven, eight, nine demos a day and just going nonstop back to back to back.
And some of them were really horrible opportunities that I still learned a lot from.
And some of them were really amazing conversations with some big brands that turned into customers and it was all about removing friction.
So it would get booked on my calendar and I would follow up right away.
Just to be clear that this is a conversation with a human and it's just not A random calendar invite and by sending that email and confirming with them and telling them I'm looking forward to talking to them, helped reduce any demo flakes like that.
You know, they would book and not show up.
I wanted to make sure that they were there and that they had a human connection so they would feel bad if they didn't show up for the call.

Omer (41:58.190)
Yeah, that's, that's a good lesson.
Just keeping it as simple as possible and reducing that friction.

Jafar Owainati (42:03.790)
Yeah.
Early days for me it's all about how do you remove as much of the friction as possible from an inbound standpoint and then being strategic about how you want to go outbound.
And I think for us, which was special about our space, and it's still special today, is when you ask someone who knows what an RFP is, you say, hey, have you ever responded to an rfp?
They'll say, yeah, it's a really painful process.
So the fact that it is such a visceral pain makes it more susceptible as being a opportunity to drive more inbound opportunities and meetings because people are looking for a solution for that pain versus perhaps other markets where it may not be as obvious.

Omer (42:45.280)
So, yeah, I mean, I think you guys have a really interesting story and from a product that Zach started to build and as you said, kind of was just collecting dust for some time to you guys spending the first four years bootstrapping this business.
And now, you know, I look on the homepage and you've got what I mean, I think you're close to around 800 companies, customers and you know, companies like AT&T, IBM, FedEx.
So these are some nice, nice logos and brand names to have.
And it kind of, again, I think is an interesting thing to think about where I'm kind of curious like, are these the types of customers you guys had in mind when you started out?
Because you'd said, hey, we were sort of thinking of a lower price point where people would just get a credit card out.
Was that just kind of like you just had a different understanding of the market or were you sort of focusing on smaller companies at the time?

Jafar Owainati (43:45.960)
I don't think we knew, to be honest.
I never worked in software before starting Lupio.
Me, Zach and Matt are all first time entrepreneurs.
Zach and Matt happen to have worked at high both software companies that were venture backed and learned a lot through that.
But they also weren't on the business side.
They were always more so on the technology side of the house.
So yeah, to be honest, I didn't even know what an Enterprise deal looked like.
I didn't know how much people were spending on software.
I didn't even know that there was software that cost.
You know, people would pay a million dollars for a piece of software.
And so a lot of it was very new to me at the time.
And you know, we've grown as founders, as individuals, and have learned so much more about the software market.
But early days was just learning by trial and drinking out of a fire hose and recognizing over time that like, oh shit, like these big companies spend a ton of money on software.
So we did think about logos and we thought it would be cool to bring in really great, reputable brands.
We weren't necessarily thinking about the AT&TS of the world.
I think we were.
Our hypothesis in the early days was more about smaller organizations that were selling to larger organizations because the question becomes who's issuing the RFP and who's responding.
But it is important to Note that like AT&T and FedEx are also getting RFPs that they need to respond to regardless of their scale as a business.
So it was just learning as we went.
We really were growing and learning and just figuring it out and I think that's okay.
Obviously, when people talk about being first time founders versus second time founders or even third time, I definitely see the value.
Like if I was starting another company, I know so much more now than I did when we first started this business.
And there's so much that I would be able to accelerate in terms of the building process if I was going to start another business.
But I wouldn't give up the early days and, and all the stuff that we learned.
It was amazing.

Omer (45:53.190)
Yeah, that's, that's awesome.
Okay, we should wrap up and move on to the lightning round.
So I'm going to ask you seven quickfire questions.
Just try to answer them as quickly as you can.
So you ready?

Jafar Owainati (46:08.320)
Ready.

Omer (46:08.960)
Okay.
What's the best piece of business advice you've ever received?

Jafar Owainati (46:12.640)
Hire people who love doing the things that you hate doing.

Omer (46:16.000)
What book would you recommend to our audience and why?

Jafar Owainati (46:19.040)
I think for this audience, a book that I think is really great is Dear Founder by Maynard Webb.
It's a series of letters that are sort of targeted to founders and lessons that people should consider.
And it walks through almost like the entire journey from when you first start a business to what it means to sell your company and things to consider.
I don't think that it's perfect, but I think it's good advice and things to be aware of.

Omer (46:45.690)
What's one attribute or characteristic in your mind of a successful founder.

Jafar Owainati (46:50.330)
The ability to learn extremely quickly and being able to apply what you learn in the context of your business.

Omer (46:58.090)
What's your favorite personal productivity tool or habit?

Jafar Owainati (47:01.830)
I started using multiple inboxes in Gmail.
I can't remember where I got the information on how to configure it, but it's basically, it's a path to zero inbox.
I have a different inbox for urgent items, for lower priority action items, things to follow up on, things that have been delegated and it just, it's been life changing for me.

Omer (47:24.790)
What's a new or crazy business idea you'd love to pursue if you had the extra time?

Jafar Owainati (47:29.040)
I think for me it's less about the idea and more the type of work that I want to be doing.
I would be really interested to do a business that's more consumer facing because I think the challenges are very different than a business to business solution.

Omer (47:46.320)
Yeah.
What's an interesting or fun fact about you that most people don't know?

Jafar Owainati (47:51.120)
To be fair, I feel like this question gets asked so much that I think everyone knows my fun fact now.
But for me, I was huge into skateboarding growing up and When I was 13 I competed in the Vans Warped Tour amateur contest.
I think I got 40th place or something like that, but I was still really happy that I put myself out there.

Omer (48:13.040)
I don't know anything about skateboarding.
Is that a big tournament competition?

Jafar Owainati (48:18.000)
Yeah, it was basically a street skateboard competition and we had 70 people competing in the one that I did.
But it was Vans being a huge shoe company and the Vans Warped Tour especially back then was one of the biggest sort of skateboard contests out there.
This was sort of like a path to get to the main one, but it was a nice experience to go through as a, as a young 13 year old.

Omer (48:43.790)
Awesome.
And finally, what's one of your most important passions outside of your work?

Jafar Owainati (48:47.710)
For me, it's music.
I've been DJing for more than 20 years and I have my turntables still set up in my living room.
I hadn't used them in a while, but been getting back into it, I guess context for the listeners out there.
We're in the middle of COVID 19, so spending a lot more time at home and being able to spend more time with my hobbies is this like,

Omer (49:11.490)
like vinyl turntables or those kind of.

Jafar Owainati (49:15.170)
They are vinyl turntables, they're technique turntables.
But I, I do use DJ software with the vinyl.
So you basically have vinyl control records that will connect to your laptop.
And it's much easier than having to haul around a bunch of vinyl to DJ at a party.
You can just pick an MP3 on your laptop and it sort of maps on your record.

Omer (49:40.540)
That's awesome.
Jafar, thank you for joining me today and talking about Lupio.
You know, the funny thing is that I, I kind of probably as we started this conversation, I was kind of making sort of a note of some other questions I wanted to ask you.
And I was like, I didn't even get through all of those and I think it was a really good conversation.
I really thank you.
Enjoyed us talking about the early days and some of the experiences that you went through in terms of finding and talking to customers and how you figured out some of the growth channels and, and pricing and stuff.
So I think that was a really good conversation to have.
So thanks for sharing your experiences there.
Now, if people want to go and find out more about Lupio, they can go to lupio.com and we'll include a link in the show notes as well.
And if people want to get in touch with you, what's the best way for them to do that?

Jafar Owainati (50:35.260)
They can email me.
It's just jafar j a f a rupeo.com Feel free to also add me on LinkedIn.
Always happy to connect with people.

Omer (50:44.830)
Awesome.
Thank you.
And I wish you, Matt and Zach all the best of success.