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Home/The SaaS Podcast/Episode 321
She Gave Her SaaS Away Free for 18 Months. Here's What Changed.
Cristina Vila, Cledara

She Gave Her SaaS Away Free for 18 Months. Here's What Changed.

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Episode Summary

Cristina Vila spent 18 months giving Cledara away for free. She had no way for customers to pay, no SaaS pricing plan, and activation was stuck at 50%. Then she started charging - and everything changed.

When Cledara introduced its first paid plans, activation jumped to 80%, perceived value increased, and customers started converting faster. A year later, Cristina raised prices again with zero impact on sales. That single SaaS pricing decision unlocked a path to $2.4M ARR and over 710 customers.

Cristina Vila is the co-founder and CEO of Cledara, a product that helps companies simplify the way they discover, buy, manage and cancel subscription software.

In 2018, Cristina quit her job to start her SaaS business. She was a first-time founder, who didn't know how to code and didn't have any sales experience.

But she was driven by a life-long dream to one day start her own business.

After raising a pre-seed round, she hired a software development company to build the product which she launched at SaaStock in Dublin three months later.

But when she tried to sell her product, she got a lot of objections.

Some people said that they didn't have a problem managing software subscriptions, others felt they already had a good solution in place (even if it was just a spreadsheet), and a lot of other people just weren't interested at that time.

So for a while, things weren't looking good for Cristina.

And even worse, she didn't charge for her product for 18 months. In fact, there wasn't even a way for customers to pay for her product - which many would say was a rookie mistake.

Despite those challenges, Cristina and her co-founder Brad, have grown Cledara to $2.4M in ARR so far with over 700 customers. And they've raised $7M and built a team of nearly 50 people.

Topics: Pricing & Monetization|First Customers|Fundraising

Key Insight

Cledara CEO Cristina Vila gave her SaaS product away for free for 18 months, only to discover that introducing paid plans increased activation from 50% to 80% and boosted perceived value so much that a subsequent price increase had zero impact on conversion rates - ultimately fueling growth to $2.4M ARR and 710 customers.

Key Ideas

  • Cledara ran without any payment mechanism for 18 months while focusing entirely on product value
  • Introducing SaaS pricing raised activation rates from 50% to 80% because paying customers felt compelled to use the product
  • A price increase one year later had zero impact on sales velocity, signaling significant remaining pricing headroom
  • Initial plans started at 10 GBP/month and later moved to 100, 300, and 500 GBP tiers
  • Outbound email campaigns asking prospects about their SaaS management pain drove the growth from 100 to 710 customers

Key Lessons

  • 💰 SaaS pricing creates activation urgency: Cledara's free users activated at just 50%, but once paid plans launched, activation jumped to 80% because financial commitment pushed customers to actually onboard and use the product.
  • 📉 Raising SaaS pricing revealed untapped value: One year after introducing paid plans, Cledara raised prices with zero impact on conversion rates, proving they had been significantly undercharging relative to customer-perceived value.
  • 🎯 Target companies where the pain is undeniable: Cledara initially sold to 20-person companies that could still cope with spreadsheets. Moving upmarket to 50-500 employees meant every prospect already felt the SaaS management problem acutely.
  • 🤝 Use prospect education as a delayed sales tactic: When prospects said they had no SaaS problem, Cristina told them to audit their tools internally. Within 3-6 months, most came back after discovering 30-40 unknown subscriptions.
  • 🚀 Create a forcing function to ship faster: Cristina committed to launching Cledara on stage at SaaStock Dublin before she even had a product, using the pitch competition deadline as a non-negotiable MVP launch date.
  • 💰 Adapt your SaaS pricing pitch for virtual fundraising: Zoom killed the conversational energy of in-person investor meetings. Cledara switched to metric-heavy slide presentations that kept investors visually engaged with growth charts.
  • 🛠️ Hire a dev agency for speed when you are non-technical: Cristina used a development company instead of full-time hires to build the MVP in three months, gaining flexibility to bring in specialized expertise as needed.

Chapters

00:00Introduction
02:04Cristina's motivational quote from her mom
02:40What Cledara does and who it serves
03:12Revenue, team size, and customer count
03:53How Cledara differs from Brex, Ramp, and IT tools
05:41Origin story at a neobank startup
08:18What pushed Cristina to quit and start Cledara
09:54Building the MVP in three months for SaaStock Dublin
12:34How co-founder Brad joined the company
12:58Hiring a dev agency as a non-technical founder
14:00Defining the MVP scope with virtual cards
15:15First customers from the SaaStock pitch competition
16:12Why Cledara was free for 18 months with no payment system
17:51Runway and pre-seed funding without revenue
20:15How charging increased activation from 50% to 80%
21:55Initial pricing tiers and raising prices with no impact
22:12Getting to the first 100 customers through founder-led sales
23:28Self-serve onboarding plus a fintech KYC requirement
24:33Common objections and the delayed realization tactic
28:50Fundraising during COVID and adapting to Zoom pitches
33:46Outbound as the growth engine from 100 to 710 customers
38:10How Brex and Ramp educated the market for Cledara
39:24Lightning round

Episode Q&A

How did Cledara's SaaS pricing shift increase activation from 50% to 80%?

When Cledara started charging, customers who paid felt compelled to actually use the product. The financial commitment created urgency to onboard and reach the value, whereas free users had no incentive to prioritize activation.

Why did Cristina Vila give Cledara away for free for 18 months?

Cristina deprioritized building a payment system because she was focused entirely on product value and customer feedback. She believed charging was less important than making the product useful, so she kept pushing it down the roadmap.

How did Cledara grow from 100 to 710 customers using outbound sales?

After raising a seed round in November 2021, Cledara hired a head of sales from SaaStock who ran pain-focused outbound emails asking prospects about their SaaS management symptoms. The response rates were high because the problem resonated immediately.

What SaaS pricing strategy did Cledara use when it first started charging?

Cledara launched three plans at 10, 30, and 90 GBP per month. After proving demand, they increased prices to 100, 300, and 500 GBP with no impact on conversion, indicating significant pricing headroom.

How did Cristina Vila overcome the objection that prospects didn't need SaaS management?

Cristina told prospects to go ask their teams how many software tools they actually used. Typically within 3-6 months, those same prospects returned after discovering 30-40 unknown subscriptions and significant waste.

What fundraising lesson did Cristina Vila learn when raising Cledara's seed round during COVID?

Conversational Zoom calls failed to engage investors the way in-person meetings had. After a Techstars advisor suggested showing slides, Cristina switched to metric-heavy visual presentations that kept investor attention focused on growth charts.

How did Cristina Vila build Cledara's MVP in three months without knowing how to code?

Cristina raised a small angel round and hired a development agency that could flex additional expertise as needed. She used SaaStock's pitch competition in Dublin as a forcing function, committing to launch on stage in October 2018.

Why did Cledara move upmarket from 20-person companies to 50-500 employees?

Companies with fewer than 50 people could still manage SaaS subscriptions manually. At 50+ employees, coordination breaks down, finance teams struggle to track invoices across departments, and the pain becomes acute enough to buy a solution.

How did competitors like Brex and Ramp actually help Cledara grow?

During the pandemic, Brex and Ramp started messaging around software spend management since travel expenses disappeared. This educated the market about the SaaS management problem, so when prospects found Cledara, they already understood the need.

Book Recommendations

Team of Teams: New Rules of Engagement for a Complex World

by Gen. Stanley McChrystal

Links

  • Cledara: Website | LinkedIn | X
  • Cristina Vila: LinkedIn | X
  • Omer Khan: LinkedIn | X
Full Transcript

Omer (00:09.280)
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 Christina Villa, the co founder and CEO of Cloudara, a product that helps companies simplify the way they discover, buy, manage and cancel subscription software.
In 2018, Christina quit her job to start her SaaS business.
She was a first time founder who didn't know how to code and she didn't have any sales experience.
But she was driven by a lifelong dream to one day start her own business.
After raising a pre seed round, she hired a software development company to build the product within three months which she launched at saasdoc in Dublin that year.
But when she tried to sell, she found she was getting a lot of objections.
Some people said that they didn't have a problem managing software subscriptions.
Others felt they already had a good solution in place even if it was just a spreadsheet and a lot of other people just weren't interested at that time.
So for a while things weren't looking great for Cristina and even worse, she didn't charge for her product for 18 months.
In fact, there wasn't even a way for customers to pay for her product, which many would say was a rookie mistake.
Despite those challenges, Christina and her co founder Brad have grown Cloudara to $2.4 million in ARR so far with over 700 customers around the world and they've raised $7 million and built a team of nearly 50 people.
In this episode, Christina shares the lessons she's learned as a first time founder and how she was able to overcome so many challenges to find product market fit.
I hope you enjoy it.
Christina, welcome to the show.

Cristina Vila (02:04.640)
Yes, hi and well, great to be here.

Omer (02:07.240)
Omar, do you have a quote, something that inspires or motivates you that you can share with us?

Cristina Vila (02:12.700)
Yes.
One that actually my mom told me very early on it's.
You already have the no go for the yes.
And this has really inspired me throughout my career to just, you know, just go try it.
You may fail, that's fine, you know that.
So just go succeed.

Omer (02:29.420)
And your mom told you that?

Cristina Vila (02:30.700)
My mom told me that, yes.
Yeah.
Very, very early on in my, in my life.

Omer (02:34.860)
What great advice.
Sounds like a very wise person.

Cristina Vila (02:39.270)
Yes, yes, yes, yes.

Omer (02:40.390)
So tell us about Clidara.
What does the product do, who's it for and what's the main problem that you're helping to solve.

Cristina Vila (02:46.470)
Yes.
So at Clidara, we help companies discover, buy, manage and cancel all the different software subscriptions that they use to run their businesses.
And yeah, so they typically.
We typically work with company software companies that they have somewhere like with, you know, 50 and 500 employees.
And obviously they use tons of these software applications.

Omer (03:12.130)
Give us a sense of the size of the business.
So where are you in terms of revenue, team, et cetera?

Cristina Vila (03:18.690)
So in terms of revenue today, we are at $2.4 million of annual revenue.
In terms of team size, we have 47 great people.
And then in terms of the customers, we are at 710 as of just 10 minutes ago.

Omer (03:41.620)
And you've raised $7 million to date, right?

Cristina Vila (03:45.780)
That's correct, yes.
$7 million from great investors like Nalta Capital Notion.
And so I want to understand a

Omer (03:53.460)
little bit about cloudara and where it fits into the market, because there are similar products out there that will help you understand what subscriptions you have, and so you can manage those costs a little bit more better.
But cloudara's is a little bit different.
So can you just tell us how do you fit in that marketplace today?

Cristina Vila (04:14.060)
Yes.
So as you say.
Right.
So obviously companies have been buying software for a long time, so there are definitely ways that you can do it.
One is you just have a credit card and you pay for it, or you have and you have an Excel sheet and you can write it down and keep track of that.
Then you have something a little bit more sophisticated, which would be like a product like Brex or Ramp that.
Yeah, maybe they enable you to again, have the cards to pay for things and then keep track of how much you are spending.
But they don't really help you with the management itself.
And then you could.
The management of the software part.
Right.
And then you could say, well, we have companies that are more on the pure SaaS management space, that help IT teams, technology.
Okay, are people using software.
But that's very niche.
That's only for it.
And in the end, SaaS is used across the organization.
SaaS is bought across the organization.
So at Cloudata, what we're doing is we are building a solution that enables the whole company to, let's say, participate in that journey of SaaS within the company.
And that's from the moment that you say, well, I need to buy something or I need to discover even what I want to buy.
And then you can buy it through us, and then you can do the ongoing management through us.
So we do that end to end flow.

Omer (05:41.080)
Got it?
So let's talk about how you came up with the idea for this business.
So what were you doing at the time and where did the idea come from?

Cristina Vila (05:50.280)
Yeah, that brings great, you know, both painful and positive memories.
So I was at the, at the previous startup that I was working.
It was a neobank for emerging markets that we were building and I was running the middle and back office operations for them and we were growing quickly and of course we had to scale.
So I was looking at the processes and part of that is, okay, which software are we using in the different parts of the business, why are we using it, who is using it, and obviously how much are we paying for this?
Right.
And, and should we continue using that particular product?
And turns out it was very hard.
So software was everywhere.
Like everyone was buying tools nonstop.
And then when I started digging in, it was like, okay, we have a product here that we are paying for that nobody's using.
We didn't even know we had it anymore.
Like we had forgotten about it.
And then other ones where the administrator of the tool had left so we had to add someone and we couldn't.
And that's because, well, you know, it's just so unmanaged at the moment the way it's so scattered across the business.
And I was looking for a solution because I was with my little spreadsheet as, okay, this is all what we're using in the business.
But as soon as I finished my spreadsheet it was out of date.
So check with other companies.
How are you guys managing this?
And what they told me is, yeah, we have a spreadsheet and we go through bank accounts and we look at expense reports and we ask people on email or Slack and when you think, well, the SaaS market is just growing 20% a year and this is not going to stop.
This is not just something that we need to kind of cope for a period of time.
In fact, the problem will become bigger because these companies that are today starting to use more and more software in their businesses, they are tech forward, they really understand technology and they don't manage to manage it, let alone then the companies that are maybe less tech forward, why would they adopt SaaS if they cannot manage it?
And you end up with waste of 30% plus on what you spend on software.
So that's where then I decided to essentially leave that job to start Cladata almost four years ago.

Omer (08:18.300)
What was it about these conversations that you had that convinced you to go and start this business?
A lot of people come across problems and they, they See that there's a potential opportunity there, and then they go back to their day job.
They don't, they don't say, I'm going to quit, I'm going to go in and do this.
So was it the, from, from the conversations you had that how much pain people were experiencing or was it purely based on, you know, what you said about the, the opportunity that you saw that was only just going to get bigger?
What pushed you to say, okay, I'm going to quit and I'm going to go and do something?

Cristina Vila (08:54.330)
So I think it's a variety of things, so.
And I would say probably the first one is that I always want to start my own business since a very early age.
But you know, the typical thing, you don't know what to do, you think you don't have enough experience, you don't know how you will do it.
So it's kind of, well, you just join a company, then you go to another one.
But that was always there.
I always wanted to have my own business and I wanted to build something great and help people.
These are the things that usually move me.
And then I saw this pain and I was like, well, that's annoying me and it's annoying everyone I speak with.
So that's definitely something that should exist.
So there is value on bringing it to the wall.
It will help people.
And then obviously the opportunity is big, so it's worth the effort of starting it, building it, and then, well, you know, in future, every company will use Cloudata because every company will use software.

Omer (09:53.910)
You decide to take the leap and go and build this, what did you do next?
Did you start going out and finding more potential customers to interview to validate this idea further?
Did you feel like you, you had enough to start building the product?
Like, what, what did you do next?

Cristina Vila (10:12.160)
So I, we incorporated the company on the 1st 9th of July, 2018.
And from then I just started talking to people, talking to investors, just people in more companies.
And if something I've learned in my experience is that in previous companies is that I had to put the product to market very quickly.
So I wanted to really get feedback from customers, people that are using it.
And so then my, my mission there was, okay, I need to launch in three months.
And then I start to think, okay, how can I do it?
And, and what can be that forcing function?
So then I realized that there was some SAS Talk, SAS conference in Dublin that I could launch at SAS Talk.
So then I thought I had two engineers by then to say, okay, we need to Build an MVP that I can launch in three months on stage in SAS talked, no pressure, not even pressure for me.
Right, because how do you know you'll be on stage?
You just started like, why would they put you there?
So then we decided to enter the, they had to pitch competition for startups.
So I applied, we got accepted and I assumed that I would win so that I could be on stage.
And you know, surprise, surprise, we did win.
So I managed to actually launch then on stage that MVP on it was in October, like mid October.
And from that we got the first crazy, first customers that decided to use that super clunky MVP that it did what it said in a very basic way, but it obviously needed a lot of work, lots of features to really improve the management.
But you could already go in, request some software in a very basic way, create the virtual card to pay for that software and then keep track on a very basic dashboard, essentially.
So yeah, so that's how we got started.

Omer (12:34.790)
How did you and your co founder Brad come together?

Cristina Vila (12:38.790)
So we worked previously at, at this Neo bank before and then I started on my own.
So I was a solo founder for the first year and a half, I think, or first year.
And then he joined me afterwards.

Omer (12:57.900)
And how did you build the product?
So you're not a developer?

Cristina Vila (13:01.740)
No, I'm not a developer myself.
So in between all that, let's say going from incorporating in July until launching in mid October, we raised a small angel round to be able to hire a couple of engineers that would then help me build this MVP of the product.
And that was an incredible exercise because obviously I have this vision for the product of all the things that I want to build and all the things that I want to bring to life.

Omer (13:36.520)
Did you hire them as, as full time employees or were these freelancers?

Cristina Vila (13:40.520)
They were from a company and yeah, that was what enabled us actually to move very quickly because then, you know, if we needed any other type of expertise that maybe these two engineers didn't have, they could bring it on board.
So that was actually very, I think it was very useful in our case.

Omer (14:00.600)
So I'm curious about how you figured out what that MVP was going to be.
Because just the idea of doing an audit or inventory of what SaaS products you're using that on its own could take three months to build a decent product.
That does a good job at that.
Right?
Because presumably you've got to connect to different sources, whether it's bank accounts or you know, whatever to, to get that information.
But then you also talked about These virtual payment cards and stuff like that.
And I'm like, was that, was that part of the MVP as well?

Cristina Vila (14:31.660)
Yes, we come from a payments background.
Right.
So we saw back then the banking as a service platforms were really starting to emerge and I saw the opportunity to bring a fintech product to life much faster than it was ever possible before.
So then we integrated to Railsbank, which is a banking as a service platform in the uk and with that we had obviously then the ability to, to create those virtual cards that then the customers would go to the platform to request so they could pay for the software that they needed.

Omer (15:10.810)
Got it.
Okay, so you got on stage at SAS Doc.

Cristina Vila (15:14.490)
Yes.

Omer (15:15.130)
You did the demo.
And those initial customers, were they just people who were at the event who saw the demo and were like, yes, I want this.

Cristina Vila (15:24.170)
Yes.
So a couple of them were from the event that they just wanted to.
Yeah, they knew that it was very early on.
So they, what I told them is, look, you know, just use it and give me feedback.
That's the most valuable thing for me.
And you know, just tell me anything that you think, things that don't work, things that you would like to see.
Because we are still creating this.
Right.
And they really believed in the, in the vision and what we wanted to build because they had experienced that pain in their companies and so they wanted to be able to use that solution.
And so, yeah, so they came from that.
And then also Railsman themselves.
As we were building the product and integrating to them, they were like, oh, that's amazing, we definitely need these.
So they also became one of our first customers and they are still with us.

Omer (16:12.240)
So yes, I spoke to a founder recently, serial entrepreneur.
Really important to him to know that he's got customers.
So he was like, it was super important for me to charge for my MVP and to make sure that's there.
And that's a theme.
Lately I've been hearing more and more about where people just keep going on about, hey, you got to want to pre sell the product.
I want to really make sure that people are willing to pay it as early as possible.
Now with you, it was completely different because you didn't charge people initially and that was probably about the first 18 months, I think.
But you didn't even have a way for people to pay for the product.
But and this is why I love having these conversations because there's no one way to go and build a SaaS business.
And it's what one person does and you think that's the way to do it.
And Then somebody does something completely opposite, and you're like, well, that works too.
Now what do I do here?
So what was your reason behind that?
I know you mentioned that you really wanted people to try the product, but 18 months is a long time not to be charging anybody.

Cristina Vila (17:07.830)
Yeah, so we.
I mean, I was just so focused on just building product that was valuable for the customer.
So every.
Every effort from engineering and talking to customers was going to extracting what would be the most valuable, what would increase the value of the product, what would make customers really continue buying and using the product.
And in the end, charging for the product was not one of them.
Right.
So it's like, okay, no, that's deprioritized.
We are not going to build this yet.
Let's just continue getting customers, more customers, more feedback.
And that was really how I was thinking about it at the time was just purely from prioritization in terms of value for customers.

Omer (17:50.960)
And those first 18 months, what did your Runway look like?
Was it really just the seed round that you'd raised, which was going to help you get through that period?
Were you tapping into savings?
How are you getting through them without any revenue coming in?

Cristina Vila (18:04.960)
At the time, we had raised a small pre seed.
I don't know if it was naive or what, but I just thought, no, no, no, like, we just need to build these and then we'll raise after.
And in fact, after that, we raised the seed round, and only after we raised the seed round, we decided to start charging for customers.
So it's okay now we are going to build it.
And the reason why we built it is because we realized that, okay, we have customers signing up, but they are not activating as fast as we would like.
And therefore it was about 50%.
Right.
So it was low.
And I said, why is that?
So we thought, well, maybe it's because they don't pay for it, so they don't feel compelled to actually start using it.
And then we thought, well, let's see if that changes the dynamic.
So then we build it, we started charging.
And not only it changed the dynamics on activation, which then increased to around 80%, but it also changed the perception of value of the product, which that was, for me, was a very interesting thing to realize because I know what I want again, I know what I want to build.
Right.
So it's not dead.
And I see all the gaps and all the things that don't fully work.
I said, there is no value yet.
Customers won't pay.
I was terrified.
The day that we say, okay, now customers need to pay.
It's like, nobody will buy this.
And when the first customer buys, they're like, oh my God, like, they actually find the value there.
And we actually started having more and more customers as a result, because it's like, okay, now that's something that there is value there and they can attribute the value that you charge them.
And the most interesting thing was that a few.
I think it was about a year later we decided to increase prices and there was no change at all in terms of will customers stop buying because now it's more expensive?
No, actually, the sales team was saying, no, there is no impact.
Customers don't question the price at all, which means that there is still more value that we could probably realize by increasing the price again.

Omer (20:14.750)
So if I understood this correctly, the people you were getting signing up, the problem was because they weren't paying for it, there was almost not enough sense of urgency to use the product.

Cristina Vila (20:28.510)
Right, Absolutely right, yes.

Omer (20:30.630)
And once they started paying for it, it was like, well, we're paying for it, we better use it.
And then that gets them quicker to the aha moment where they start to realize, okay, we're seeing value from using this product now and everything sort of fits into place.
And I think that's really interesting because intuitively you'd think giving the product away for free should be easier, Right?
Well, they're not paying anything for it.
And so of course they're going to say yes, and of course they're going to use it and try it out.
Did you find that once you started charging the customers that you already had, did you find most of them switched to paying or was there a large chunk of customers you initially lost when you introduced the paid plans?

Cristina Vila (21:11.260)
So those customers that we already had, we didn't say, okay, now we are going to charge you.
So we kept them in the okay, you are not paying.
But the thing that they wouldn't get if they were not on the paying plan was they couldn't get the rewards that we offer them as a result of buying the software through our platform.
So some customers say, no, actually, we want the rewards.
And some customers say, no, we don't want the rewards.
We prefer not to pay for the software.
So.
And then we left those ones and they are still, some of them are still not paying today because, well, in the end they were early customers.
We committed to that.
So we are very happy maintaining that promise.
But then at some point, like for any new customer, we, we start the charging and we actually see an improvement.
Yeah.
On the conversions, what were you charging

Omer (21:54.820)
when you introduced the first paid plan?
How much did you ask customers to pay?

Cristina Vila (21:58.140)
So we had three plans.
So one that was £10, one that was 30 and another one that was I think £90, something like that.
And then yeah, we increase it and now they are at 100, 300 and 500.

Omer (22:11.820)
So it sounds like the first 10 customers sort of came through.
What we just talked about sasdoc and some other sources.
What about getting to the first hundred customers?
How did you go about getting those first 100?
Was it you doing all the sales?
Tell me a little bit more about that.

Cristina Vila (22:31.910)
So for the first, for the first, let's say 30 was definitely just me doing the sale and you know, I never sold anything before which means that I had to learn it.
So it was an interesting time, like having to learn how to demo a product and do a good job and asking people to coach me on that and attend calls with me and all that.
But we got to the first 30 and then Brad joined at that point and we then had some started to do some content because again we knew that we had to raise awareness and through that we got some people interested and by going to conferences again and then yeah, those leads that would come in, we would, Brad and I would then do the sell.

Omer (23:13.650)
And so where were these leads coming from?

Cristina Vila (23:15.650)
It was mostly like they would see some content on LinkedIn or on Twitter and then they would just say, oh yeah, we are interested.
And then they would just go to the website and sign up.

Omer (23:28.350)
And then what was the onboarding process like?
Were you, were you taking people through a demo and then helping them onboard?
Was it more of a product led growth model where everything was much more about self serve, where did things fit?

Cristina Vila (23:41.150)
So we had the self serve and of course we do have a fintech element.
So there is that.
I don't know if you're familiar, like there is a KYC part which means that it's not fully served.
Like, like we have to do something on our side before the customer can actually get into the platform.
But there was a time where, yes, so they could just activate or go and do the onboarding without us talking to the customer.
And we had some customers do that and then the other ones, yeah, went through the demo and then we would help them once they went into the product, we would show them how to do things.
But it's very intuitive so you don't really need a lot of our help once you are into the product.
Definitely not.
When we were selling to smaller Companies back then, when we started, bigger companies required a little bit more help.
At the beginning, when you were going

Omer (24:33.270)
through and getting to these first 30 customers yourself, what were some of the common objections you were hearing when you were pitching the product, doing a demo?

Cristina Vila (24:43.310)
So very early on it was very curious.
They said no, no, we don't have any problem software, like they're fine.
I was like, no, no, no, no, no, you just don't know it.
Just go ask your people, ask them how many software they're using and let's see what you come up.
I'm sure it's not like the five to 10 tools that you're telling me.
And, and this used to be very common.
And then you know, you go back to the office, maybe you don't think about it, but three months later you get an email saying actually you know what, I went around, I asked and we are spending a lot, you know, and we have a lot of tools, we have like 30, 40 products that I didn't know about.
So.
And it was, this was initially a very common objection, but it was really a delay because as soon as then they realized they would come back and if the time was right for them then they would, they would on board.
The, the other thing, the other objection would be yeah, now it's not a good moment, we are fundraising or we have other priorities.
So then obviously, well when is a good time?
So we will contact you in six months.
And then another objection would have been, or it still is, right sometimes that they are already using other ways in which they, they pay for software.
But of course that doesn't mean that they can manage it.
So we usually then explain why we are different and maybe at that point they are not ready to take that decision.
But if then they start experiencing that friction as you start having more and more subscriptions in the business, then it usually again resolves further in the future that the customer comes back.
But yeah, this is usually why customers don't buy when we initially speak with them, they don't think it's for them at that point in time, they're too small.
Uh huh, things like that.
Yeah.

Omer (26:40.940)
And to overcome that objection, you have a series of questions.
You ask them to think about, not necessarily answer there and then like going talk to your people.
You said there's sort of a delay and I don't know if there's a click on answer.
But typically from that point you have that conversation where someone says to you we don't have this problem and then you tell them go and Ask your team or whatever, how much time does it take for them to.
To come back and say, yeah, we do.
We do have a problem.

Cristina Vila (27:05.350)
Yeah.
So sometimes it's.
It's three months, sometimes maybe six months.
Right.
So these.
It will vary per customer, and it will vary depending on how fast they are growing.
And if they are growing more slowly, then maybe the pain will only manifest much farther down the line.
Now, of course, what we try to do is we, you know, through all this time talking to customers, and again, this was early on when we were targeting companies of 20 people.
What we learn is, okay, at that point, it's too early.
Like, it happens that sometimes you just don't have that many maybe, or you have them, but you can still somehow manage it or you feel you can.
So then it's okay.
But once you have 50 people, then it becomes really hard because you are not in contact with everybody all the time.
So it's harder to communicate and to coordinate.
And.
And now what we've tried to do to overcome all those objections that we had is, okay, let's target companies that are a little bit bigger, because we know that for sure we'll have a problem.
And then usually what happens also at that point is you already have, which is very curious because it's an IT problem.
But it's the finance function that's trying to figure it out because they need the invoices, and they need to go around the whole organization trying to figure out who has that invoice for that piece of software.
So in the end, they have the list of, okay, Pipedrive is, you know, this person in sales, and HubSpot is this person in marketing.
And.
And like this, they go down.
So then it's like, okay, when we talk to them, they're, oh, yes, I have a list and that list.
If I could just automate it so I don't need to do all this all the time, it would be great.

Omer (28:50.360)
Let's talk about fundraising.
You learned some interesting lessons on how the process of fundraising changed in the last few years and some of the new challenges that founders face.
I think you focused on your seed round, like, just before the world shut down.
Is that right?

Cristina Vila (29:08.360)
Yeah, it was great timing.
Yeah.
So we were like, okay, we are getting ready for these.
We have everything.
And then all of a sudden, yeah, but you couldn't meet anyone.
And I said, okay, yeah, but we had said that we would do it, so let's just push through.
Right?
Let's see what happens.
And so we started, obviously, scheduling zoom calls with investors.
And, of course, what we had done in the past was where you meet people face to face, you build that relationship, you explain where you are.
And it's all very conversational.
And the reality of Zoom, right, Is that, well, we were having.
We were trying to do the same thing.
Let's build that relationship.
Let's talk to people, let's make it conversational.
But the attention that you get from people, from Zoom is very different than when you are face to face.
Right.
The level of engagement, the way in which you create that connection, it just.
So it almost sometimes cannot happen.
So then we were just not getting anywhere.
It's like, okay, great conversations.
People love the idea, but we're just not moving forward.
Like, why is that?
Like, we were so frustrated because we were growing very well.
Well, so we just couldn't understand it, so we decided to stop.
Okay, let's pause, let's pause.
Let's think.
What's not working here?
And then we were speaking with people, like, how are you going around doing fundraising these days?
And, well, people were saying, some people.
For some people was maybe working better.
And for some people was also very hard.
And then we were speaking one day with somebody from.
From techstars, and we asked him, you are interviewing companies now to join the program.
What do the best companies do?
And he said, well, they are very well prepared with slides.
So it's like, okay, we could test that.
So then we went away and we started having lots of slides.
But we took it one step further because, well, it's only slides.
Then it's like you are talking over what you are saying, which is not necessarily engaging.
So let's put numbers, because numbers keep your attention.
Oh, wow.
Why is that 20%?
And why is that chart going up?
And why is this one going flat?
Maybe it's a good thing, maybe it's not.
So then we started putting lots of numbers, and we made it more based on the figures of the business, explaining a little bit, obviously, on the story and where we want to get to, but really, really emphasizing on those great numbers the business had.

Omer (31:40.220)
So I think somebody listening to this might say, well, yeah, the pitch deck should have a focus on numbers, should talk about the size of the market, our costs, opportunity, all of that stuff.
So what was it that you were doing in addition to that?
When you say we really double down on metrics?

Cristina Vila (31:57.340)
The thing is, initially, when we were talking to investors, we were not.
So we were sharing the deck, but then we were not talking over the deck.
When we were on the call so we were having a conversation and we were not focusing so much on the metrics.
And then, yeah, what we decided to do is not let's actually.
And if we were talking about metrics, it was again as a conversation.
So then what we did is, okay, let's do intros, let's talk about, you know, how.
Where are we going in very broad terms.
But then let's put the slides up on the screen, which is not something that we ever did when we were fundraising in person.
Like putting the slides up when you are just having the first meetings.
So then we put it up and it's okay.
And here we're talking about growth.
And here you have the chart.
And here we're talking about revenue.
And here you have the chart.
And here is customers.
And here you have the chart.
So that you really go away seeing all those charts going up and to the right.

Omer (33:02.190)
Got it.
So you already had that information in the pitch deck, but it was more about the how to adapt the way you have that conversation and the information that you focus on, those zoom calls.
Because the dynamics of that were very different to what you'd been doing in.
In person.

Cristina Vila (33:21.070)
Exactly.
Because the level, look, maybe it's a thing on my side, but the way in which you can express the excitement of something is very different when you are sitting in front of a computer than when you are sitting around a table talking about something.
Right.
So your expressiveness is different.
And that is what then people can take away, but they cannot take it away through a camera as easily.

Omer (33:45.730)
Totally.
Okay, so the story so far, what we've covered is you built the MVP, got some initial customers, grew this to the first 100 customers, you raised the seed round, you started charging for the product, started getting paying customers, and then you had this period where you're going from 100 customers to 710.
Right.
What was the main growth channel that helped you go from that 100 to 700 odd customers?

Cristina Vila (34:19.420)
So for us, it was outbound.
In November 2021, we raised the seat round.
So before that we had done the P seat, so we raised that seat round.
At the time we were seven people very focused on products or four engineers by then, Brad and I doing everything else.
And then a recent graduate that joined us to help us a little bit with marketing.
So we were very, very small.
But at that point, after closing that round, we said, okay, now it's time to build the go to market function.
So we hired Oscar.
That actually came from sasdoc.
He was running sales there and he was Very strong on Outbound.
And that was important for us because this is right, we want to make sure that we could raise that awareness.
So our emails were like, hey, do you have this type of symptoms?
Do you feel that pain?
Then we're happy to talk.
It was incredible the amount of responses that we started getting out of that.
Then we also had Rob, which was the former head of international marketing for PayPal and he had also worked at a CMO of Airbase.
So he joined us as our CMO to help us with positioning because he said, well, we are a different type of product, so we need to make sure that customers understand what we are when they are looking at us.
Otherwise they're like, I don't know what this is.
So that was also something that, that has helped us with that, you know, selling to customers more effectively.
And then obviously there is the, let's say the retention part, right, so that you can grow but you don't lose.
By the time we had hundred customers, I was still the only one doing some customer support and customer success work, which was a disaster because I was a massive bottleneck.
So it's not that I couldn't attend customers well, it's just that I just didn't have the time, it had to make my top of list.
And honestly, customers are very important to me.
So it broke my heart every time I saw a customer that was waiting for two weeks to get an answer.
So then we hired Gerard that was coming from TravelPerk to help us with the customer support and customer success tasks.
So all these were the things that we put in place quite quickly after the seed round to say, okay, let's really get this.
And yeah, it was all around, okay, learning what our customers saying, what's working, what's not working.
And during that period also the market started to catch up with the awareness.
And what was very interesting is that so obviously it was the pain of raising during the pandemic, but also the blessing of going through the pandemic because some companies like Brex and Ramp started to message around spin software management because nobody was traveling, nobody was going for meals out, which meant that the only spend they had left was, well, people buying software or things online.
And then all these companies started messaging around software management, which educated a lot of the companies around the problem.
So this really helped us because then it's okay, we have this product, they're telling us they help us with this, but actually, you know what?
Not really, I still have a gap in here.
So then they, they start looking for A solution and then they find us or when we talk to them then they yeah, yes, definitely.
I need this.
And this is what helped us then grow obviously much faster to the 700 that we have now.

Omer (38:09.740)
So a few years ago it sounded like you had a bigger awareness problem and talking to customers who were saying we don't have this problem, we don't need your software and you're having to spend more time and effort educating those people that the problem does exist, that they do need to solve it, etc.
And with a number of these factors over the last few years, you're now in a situation where probably you still have people in the awareness stage that you need to educate about the problem.
But there's more of them in that next level of the funnel at the consideration where you don't.
That's not where the conversation is starting anymore.
They already know they have a problem and they're looking for the right solution or the right way to solve that problem.
And I think as you talked about beginning in terms of this, the landscape here, this is a problem that's probably just going to keep getting bigger and bigger for most companies out there.

Cristina Vila (39:01.300)
Yeah, absolutely.
I mean there is only more software being created every day and sometimes even when we speak with investors they tell us, well, you know Christina, we are helping you make the problem bigger by funding all these software companies out there.
So we definitely need to a product like, like yours in, in the market.
So.
So yeah, definitely.
It's just getting bigger and bigger.

Omer (39:24.120)
All right, we should wrap up.
Let's get into the lightning round.
I've got seven quick fire questions for you.
Just try to answer them as quickly as you can.
Are you ready?

Cristina Vila (39:31.520)
Yeah.

Omer (39:32.200)
What's the best piece of business advice you've ever received?

Cristina Vila (39:34.920)
Talk to customers and talk to as many people as possible.

Omer (39:39.000)
What book would you recommend to our audience and why?

Cristina Vila (39:41.720)
Team of teams from General Stanley McChrystal.
Because it's a great story about how the US army really improved the way in which they or changed the way in stay communicated so they could then empower teams on the ground to take decisions faster.

Omer (39:57.300)
What's one attribute or characteristic in your mind of a successful founder?

Cristina Vila (40:01.620)
Definitely to be very calm.
It's very necessary because you'll have lots of highs and lots of flows and you just need to keep it calm.

Omer (40:10.180)
What's your favorite personal productivity tool or habit?

Cristina Vila (40:13.540)
Walking and talking.
I love it.
It's when I get my best ideas.

Omer (40:18.470)
What's a new or crazy business idea you'd love to pursue if you had the extra time.

Cristina Vila (40:22.230)
So I don't know if it's crazy, but I would love to start the drinks business because I don't drink a lot of wine or beer and I would love to have a drink that has not tons of sugar but has an adult flavor that I could use with my meals.
So I would definitely spend time on that.

Omer (40:39.830)
Interesting.
What's an interesting or fun fact about you that most people don't know?

Cristina Vila (40:44.080)
I love learning things and learning how things work to the point that I went and joined or learned how to do trapeze jumping so that I could see how people can actually do that and realize that the secret is trust and lots of fitness.

Omer (41:01.680)
And finally, what's one of your most important passions outside of your work?

Cristina Vila (41:05.040)
Hiking and nature.
I'm just always amazed by the elegance and equilibrium of of nature.
It's just so beautiful.

Omer (41:14.550)
Love it.
Awesome.
Thank you so much for joining me and sharing your story and the lessons you've learned along the way.
I think there was a ton of really useful things that you shared that I'm sure people who are a little bit behind you in terms of their business are going to get a ton of takeaways and some actionable things that they can apply to what they're doing.
If people want to learn more about Cloudara, they can go to cladara.com, that's C L E D A R A. I'll include a link in the show notes so it's easier for people to get to it.
And if people want to get in touch with you, what's the best way for them to do that?

Cristina Vila (41:45.890)
Yeah, they can email me directly@christinaudara.com.
yeah, I'll be very happy to chat.

Omer (41:52.610)
Thank you so much.
It's been a pleasure and I wish you and the team the best of success.
And say hi to Brad for me.

Cristina Vila (41:58.530)
I will.
And thank you very much for having me in the show.
Thanks.

Omer (42:02.610)
My pleasure.
Cheers.

Cristina Vila (42:03.810)
Ciao.
Thank you.

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