11 Years Bootstrapped Then Funded to Build Enterprise SaaS

Omer (00:09.760)
Welcome to another episode of the SaaS Podcast.
I'm your host, Omer Khan and this is a 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 Neha Sampat, the founder and CEO of ContentStack, a headless CMS that empowers businesses to manage and deliver digital content across various channels and devices.
In 2018, Neha spotted an opportunity to transform a services focused company she'd been running for several years into an enterprise SaaS business.
Content Stack started out as just a simple form for editing mobile content without requiring developer involvement.
Today, the company has raised $169 million, grown to a team of over 200 people, and is trusted by many of the world's top brands.
In this episode you'll learn about Neha's journey of bootstrapping content stack for the first 10 years and the valuable lessons she learned from that experience.
Where you talk about how NEHA tackled challenges such as balancing short term revenue goals with long term vision and navigating a male dominated industry.
We also talk about the process NEHA used to transition Content Stack from a services focused business to an enterprise SaaS company, and the surprising reason behind Neha's decision not to raise any money for the first 10 years and the lessons she's learned from raising $169 million.
It's an inspiring story emphasizing the importance of perseverance, customer focus, and building a strong team and culture.
So I hope you enjoy it.
Neha, welcome to the show.

Neha Sampat (01:40.690)
Hey there.
I'm happy to be here.
Thanks for having me on.

Omer (01:43.730)
Do you have a favorite quote, something that inspires or motivates you that you can share with us?

Neha Sampat (01:48.050)
Absolutely.
This is something I start almost all of my big all hands meetings with at Content Stack.
And that is if it was easy, anybody would do.
And it's kind of stuck with me as an entrepreneur for all these years.

Omer (02:00.750)
Yeah.
Love it.
So tell us about Content Stack.
What does the product do, who's it for, and what's the main problem you're helping to solve?

Neha Sampat (02:08.590)
For sure.
Yeah.
So Content Stack was founded in 2018, spun out of a services company that I used to run called Raw Engineering.
We are now 450 people across 18 countries and we've raised 169 million of capital since we started.
So, you know, well on our way with our series C under our belt.
So we help a lot of large brands like Asics and Chase and Holiday Inn.
And Express and Mattel and others to carry out their visions for digital experiences.
And when we think about digital experiences, that means what they're showing on the web to engage with customers, but as well all the other omnichannel ways that people are consuming digital content, like mobile apps, billboards, smartwatches and other things.
So really, we've created a product that allows you to build digital experiences at the speed of your imagination.

Omer (03:00.130)
So when I was looking into Content Stack, it was described as a headless cms.
From what I understand, it's more than that as well.
But for people who aren't familiar, can you just explain what that term means?

Neha Sampat (03:16.610)
Yes, it's my.
My favorite term that I hate.
Headless is such a gruesome term, but in technical terms, essential.
What it means is that if you're familiar with the term API, it's the API layer.
So when you think about a website, for example, you've got sort of the brains or the heart behind the website, and then you've got the presentation layer, which is what you consume as an end user.
So when you go to a website and you're looking around, you're seeing what is the head or the presentation of the content.
What's really happening behind the scenes is that there's a lot of code and there's a lot of structure to if someone clicks on this, then show this type of logic.
That's the piece that Content Stack empowers.
The front end, or the head is the part that's built by the customer or the end user of Content Stack.
So headless basically separates the presentation layer from the code.

Omer (04:11.439)
And one of the benefits of doing that is rather than having somebody going off and creating a piece of content and designing a web page and how it's going to look and be laid out, et cetera, you give people a way to basically kind of enter that data into the CMS and then it can get rendered in all different kinds of ways.

Neha Sampat (04:34.780)
Absolutely.
You said it right.
And so it's basically, it's like the heart behind all of the content that you care about and all the logic that goes with that, how it's consumed or presented.
It could be mobile, it could be a smartwatch, it could be any type of display.
Where digital content exists, and being able to build that logic once and then deploy it to all the different places is the power of the platform.

Omer (04:56.790)
Great.
And you gave us some impressive numbers a little earlier.
And you talked about $169 million that you've raised and the size of the team 450 people.
I think it's also important to point out that you bootstrapped the business for the first 11 years.
So that's an interesting part of the story as well.
And we're going to talk a little bit about that a bit later before we.
We sort of get into, like, how you came up with the idea, or maybe this will lead to how you came up with the idea.
Like, what were you doing before you started Content Stack?

Neha Sampat (05:35.050)
Yep.
So prior to Content Stack, I was running a digital services agency called Raw Engineering.
And prior to that, which led me to Raw Engineering, I was.
I was building and running the web store for a large Fortune 1000 company called VMware.
And that was very early days of E commerce.
We were still figuring out, you know, what the best practices were for web as a channel.
And what I found is in large companies, VMware was not alone in this.
It becomes really hard to do really cool things very fast because there's a lot of red tape and there's a lot of processes, and you have to go through five committees to get anything approved.
And I really wanted to, like, the impetus was I want to unblock that.
I want to make it easy for talented people to use their talent inside organizations.
And that's powerful for the industry, individuals who are talented, but it's also really powerful for enterprise organizations that want to unlock that talent.
So I started Raw Engineering to essentially help to unlock that talent through services.
And the idea was, let's find those people that are super talented and that want to do cool things, but help them use the technologies they have and also supplement that with the right services or other tools.
And what we found is, two to three years into that journey, everybody was trying to do really cool things for mobile, and there was nothing out there that allowed them to do that.
So we created the first iteration of Content Stack, which was a very simple form for you to be able to edit content in mobile without having to go to it, without having to file tickets, without having to wait for a developer that empowered business users to do really cool and interesting things, engaging their end users and changing inventory on the fly to address demand and personalizing experiences and all that good stuff.
So that was the beginning of realizing that there was something big missing in the market and we could help address that pain point.

Omer (07:22.450)
So when you built that first version or the form, were you thinking about this as a product or was this like, hey, this is just something which is going to make it easier for us to run our services business?

Neha Sampat (07:32.050)
It was A little bit more the latter, to be really honest.
It was sort of empowering.
We had a very services, DNA services mindset.
So it was really empowering our customers to be able to do things faster.
And we did sell it as a product.
It was an add on license to our services, but we were really a services business at the time.

Omer (07:52.000)
All right, so at what point did this, this tool, like, what point did it become a product?
At what point did you see that there's a, there's a bigger opportunity here and ultimately you want to be running a product business.
Like not, not, not, not in terms of like how long it took you to kind of make that transition?
Because that's the next part of the question.
But like, when did you have that aha moment?

Neha Sampat (08:16.570)
Yeah, for sure.
So kind of on that timeline.
Right.
So 2011, we realized we need to build something to make it easier.
So we by 2012 had that offered to some of our services customers.
By 2013, it became a product that was kind of a mobile CMS, if you will.
And by 2014, Forrester had written the first report in the market about the pioneers of Headless cms.
And Content Stack was named among those pioneers.
There were three companies named at the time.
And so by 2014, there was product market fit and an opportunity.
And that's when we had the light bulb that we should be selling this as a product and not just an add on to our services.
That was the beginning of us selling Content Stack as a standalone content management system, as a software license without necessarily attaching our services.
That was the beginning of that journey.
By 2016, we realized the market was even bigger than we anticipated.
And by 2017 we decided to split the companies into three.
And January 1st of 2018 is when we spun Content Stack out of RAW Engineering and it became a standalone company.
And through that whole part of the journey, we were fully bootstrapped.

Omer (09:24.570)
And is the services part of the business still up and running or did you eventually shut that down and focus on the product completely?

Neha Sampat (09:33.220)
So I'm not playing an operating role at Raw Engineering anymore, but it still is a standalone company that's operating.

Omer (09:39.300)
Got it.
Great.
Okay, so let's talk about like, at what point?
Like you described the first version of Content Stack as a simple form that made life easier for people to publish stuff on mobile.
But at what point did you feel like, you know, there was a product that you could actually feel good charging people for?
And what did it do at that point?

Neha Sampat (10:02.590)
Yeah, so it evolved from 2011 to 2014 into a more full fledged content management system, which essentially is the first variation of what we have today with content management.
It powered the whole backend of websites, mobile apps and all types of other digital displays.
And it did it in a way that was complex enough to create integrations to anything else with a quote unquote API.
And there were user privileges built in and all kinds of other complexities that businesses would typically need in order to build out an enterprise level web experience or digital experience.
So that was in the works.
So between 2011 and 2014 is really when we did a lot of heavy lifting and turning it into a full fledged CMS product.

Omer (10:51.530)
And what were you charging for the product at the time?

Neha Sampat (10:55.020)
It went from gosh, I think at the beginning we were probably charging 250 or 300 bucks a month and now we have customers paying a million dollars a year or more.
So it's been quite the journey.
It's a big spread.

Omer (11:09.740)
So I'm trying to understand who is your target customer here?
I come from a completely different world.
So when someone says to me CMS, I'm thinking about WordPress and Webflow and all of these kinds of things and to know that not only is there an opportunity or a market out there for a product like Content Stack, but actually it's a really big opportunity.
Right.
So who are these customers?
Like who is your ideal customer?
Like when you shifted to the product focus back then, maybe that's the same target customer today, maybe it isn't.
But what were the types of companies that you were going after?

Neha Sampat (11:55.120)
Yeah, I'd say in the earlier days because the term headless CMS or even just the idea of APIs were so new.
If you think about when people talk about building software now, they talk about monolithic versus API or microservices based.
And we've always been in the microservices based camp.
So two or three years ago it was only really early adopters or people that had a vision for microservices being the better way that were engaging with us.
Today we're kind of in what I consider the early mainstream of brands deciding that microservices or composable or API first, there's a lot of terms for it is the way to build software.
We went from finding the change makers in organizations to now what is typically a regular part of any content management system evaluation at any large business.
And when I think about large businesses, I'm thinking Fortune 1000 businesses or businesses that have digital as a core part of their strategy or infrastructure.
And then inside those organizations, it's typically someone who's leading digital, that has sort of the digital side of marketing as part of their charter, or even the head of IT or in the CIO world.
And often and most times, it's someone on both the business side and the technical side, because they have to come together to figure out how they're going to not only build something really awesome, but do it in a way that's going to have an impact on the bottom line of the business.
And so we typically are selling into multiple parts of an organization in a deal.

Omer (13:31.810)
So when you and I were talking before we started recording, I asked you about where your initial customers came from, and you said, inbound.
And I was like, no, that was after all the hustle of the first 10, 20, 30 customers.
And then you started kind of getting inbound working, and you said, no, no, no.
Inbound work, like, pretty much from day one.
Can you tell us about that?
Like, as I said to you, I think that's a founder's dream.
Build a product and customers just turn up.
Like, what was it that allowed that kind of situation, you know, to work for you?

Neha Sampat (14:06.120)
Yeah, I mean, if you go back to, like, just thinking about that time, it was such a critical time in digital transformation for the industry.
There was three main things that were driving that, the first of which was companies were starting to adopt cloud computing and moving away from buying everything that they then had to install and manage on their own servers.
And then you had the advent of mobile applications with the iPhone coming out in 2008, and that then starting to impact how enterprises thought about mobile and bringing mobile to work.
And do I have to build mobile apps now for my employees?
And then the third piece, which is the beginning of the SaaS world, right?
So software as a service, empowering people to kind of democratize the productivity tools they use at work or the things that they do to be more creative at work.
And so all of those coming together created a little bit of a mess because nothing was like talking to each other.
People were, like, taking things into their own hands to move quickly because they were so frustrated with, with, you know, the IT challenges that they faced inside organizations.
So that led to looking for something that would help them manage all this stuff.
And when they were looking for that, because we were one of the very early headless CMss, they found us.
It was us being one of the first websites that had headless CMS in the header.
So we were just at the right place at the right time and addressing A really big need in the market.

Omer (15:33.980)
Is that what people were searching for, like headless CMS solutions?

Neha Sampat (15:37.100)
It was often headless CMS because that was a term that even the analysts had started to use.
Or mobile content management or API based content management.
Those were kind of the main terms that drove people towards us.

Omer (15:52.620)
And the analysts, like this was like Gartner or folks like that talking about these terms, correct?

Neha Sampat (15:57.420)
Yeah.

Omer (15:57.780)
Okay, got it.
Okay.
And so there's not many out there at the time.
And so people are finding you and discovering Content Stack.
How did you figure out what to charge for for the product at the time?
You know, $250 a month compared to, you know, $1 million plus a year are worlds apart.
And I'm sure the product has evolved and improved and does, you know, delivers a ton more value, but it still seems like a huge difference.
So was it about right for what the product did at the time, or was it just kind of like, you know, a random number you just came up with?

Neha Sampat (16:38.460)
Really honestly, like as a startup, we were pricing probably lower than we needed to, and it was really just to kind of get the attention and learn.
We eventually figured out how much value we were really providing to brands.
We were figuring out how much it would cost us to scale the software and manage the software.
And we eventually landed on three different tiers of pricing that matched the needs of businesses.
And typically it would be based on the number of digital properties they were using, the number of users that were engaged.
And then sometimes there was like add on features or add on SLAs that we would build into the pricing.
And so a lot of it was just like triangulating.
Right cost, willingness to pay and budgets and value that we're bringing to the table.

Omer (17:22.290)
Can we talk?
I want to talk a little bit about onboarding and I want to try and figure out what was the process or the steps that a customer had to go through to adopt Content Stack.
Obviously, if they're using a different CMS or monolith solution, as you kind of described it, they can potentially run it in parallel and start doing testing small things.
Or maybe they have to figure out what that migration looks like.
But either way, it sounds like a lot of work, a lot of complexity and a lot of potential pain for a customer.
So number one, they probably have to be like super motivated to want to do all of this and make these changes.
And two, what kind of issues were you seeing and what, if anything, were you able to do to make that onboarding easier for customers?

Neha Sampat (18:14.730)
So the beauty in all of this is monoliths are hard and they're complicated and they require a very specialized skill set.
So you have to have special systems integrators or very specialized and expensive talent inside your organization to run and manage and implement those systems.
The difference with a headless CMS is you provide SDKs that are very common languages to be able to implement against it.
SDKs are software development kits.
And so if you have a web developer that knows how to do HTML, CMS and some JavaScript, they will be able to do what another developer that's probably three to four times as expensive can do on a monolithic system.
So it cuts out some of the complexity and the cost and empowers more people to be able to do more with the software.
Then to the flip side of someone has to be very motivated.
They are motivated because they are trying to do things.
They'll buy software, they'll spend millions of dollars in the combination of the license plus the systems integrators or services component, and it will take them one, two, sometimes three years to get to where they thought they would be able to get in six to 12 months.
And by then they've already made the investment.
They kind of have to see it through, but there's so much frustration there that they want to do something different the next time.
And that's where we really shine because we can help them make that happen and we can help them make it happen pretty fast.

Omer (19:47.560)
Let's talk about the first 11 years of bootstrapping the business.
I know you don't disclose revenue, but ballpark, where were you at the end of those 10, 11 years as a bootstrap business?
Were you over a million ARR?
Multiple seven figure business?
And generally, how many customers did you have then?

Neha Sampat (20:10.910)
When we spun out Content Stack from raw Engineering in 2018, we had a couple dozen customers and we were over a million in ARR.
So it was a good head start for sure for having bootstrapped and not having ever raised any capital.
But there was only up to go from there essentially and it wasn't an easy ride to get to that point.

Omer (20:33.950)
Did you try to raise money during that period or were you just committed to the idea of just bootstrapping?
What was your driver or your motivation to bootstrap for so many years?

Neha Sampat (20:47.130)
Honestly, in hindsight, we just didn't really know better.
I kind of was doing what I knew how to do and I knew how to build a profitable services business that could fund the R and D aspects of the other side projects.
I actually had three SaaS businesses underneath the raw engineering umbrella.
And in hindsight, I would have probably raised money a little bit earlier, maybe one to two years earlier, in order to really give Content Stack the go to market team, it needed to get ahead of the market.
But we didn't.
We did what we knew how to do, which was continue to bootstrap and just like, you know, the crawl, walk, run approach of add one more person when we could afford it, add one more person when we could afford it.
So we probably lost the opportunity to get a lead in the early market share because of that.

Omer (21:34.210)
And then when you did decide to go out and raise money, was that fairly easy given the traction that you already had and you're a seven figure business?

Neha Sampat (21:46.450)
It should have been easy, but in reality, not really because we still had to prove ourselves as a SaaS company.
So we spun out of a services company.
It was kind of our first run at being a SaaS company.
And whenever we had conversations with investors, there was the sort of hesitation or reluctance because they didn't know if we knew how to do it.
So it wasn't as easy as it should have been given our numbers and our metrics.
But we got there eventually.
And the reality is by the time we raised capital, it was like late 2019.
So we had continued to run the business, we had continued to build on it.
I was able to get some seed capital in through a convertible note, which gave us enough Runway to build out the go to market team.
And by the time we raised our Series A, we were able to do a pretty large Series A at a high valuation just because we had grown so much in a year and a half.

Omer (22:42.330)
Was this the first time that you'd raised money?

Neha Sampat (22:44.410)
Yes.

Omer (22:45.370)
What were the main kind of challenges that you had to overcome?
You talked about kind of proving yourself as a SaaS business, but what, what were investors expecting to see from you?

Neha Sampat (22:56.970)
So I think the biggest thing is I didn't really know how and in hindsight, I probably would have gotten some better coaching or had someone on my team that had done it before.
I always encourage founders to find a coach or find somebody like a mentor to help them through the process because it's actually after you've been through it a few times, it's not that complicated.
It's just how you.
The first impression is so important.
And I was so passionate about my team and the product that I was less focused on maybe some of the metrics that they cared about or other things not because they didn't Exist, but because I just wasn't really clear on how to present them.
So, yeah, I mean, in terms of the metrics, there's always the common words like how much traction do you have?
Prove that you can still have this traction once you've spun out.
We had all of that.
That wasn't really a problem.
It was probably more in how we presented it.
To be fair, I also don't look like a typical founder, and so I think that that automatically creates a little bit of a barrier.

Omer (23:56.470)
What do you mean by that?

Neha Sampat (23:57.750)
Well, as you probably know, only about 3% of all venture capital goes to female led companies.
So already it either it kind of sets you apart or it creates some sort of a bias that you may or may not really realize exists.
So I think that was something that was happening.
I didn't realize it was happening until much later.

Omer (24:18.380)
I spoke to a founder, actually two women led SaaS business, and she had actually, before starting the SaaS business, had served active duty in Afghanistan and done all kinds of crazy things, jumping out of airplanes and parachutes and things like that.
And she was talking to investors and they were asking her, you know, do you really want to do something this hard?
And she was like, you know, I've, I've done hard things.
Right.
It's like, I don't know why you think that this is going to be any, any harder for me, but yeah, it's kind of a. I like to think that that situation is improving, but it's still, it's, it's still certainly challenging, I think, for, for, for a lot of female founders.
So how long did it take to actually close that first round?

Neha Sampat (25:12.640)
So we didn't start fundraising until a few months after we spun out.
And then by the end of 2018, so probably six months into the process, I closed the Convertible Note, and then it was a year later that I closed the Series A.

Omer (25:29.680)
So we talked about Inbound as being, you know, the sort of the stars aligned and all of these external circumstances, and you had people looking for a solution like yours, and that eventually got you up to kind of like the Series A stage.
You then had to focus a lot more on demand gen and education.
Tell us a little bit about that.
What was the shift you had to make?
What were some of the challenges that you were starting to see in terms of customer acquisition?

Neha Sampat (26:02.980)
You know, the inbound is still, is still a big part of how we get leads today, which is really great because as the market's getting educated, they find us like we, you know, we've been out there for a long time, but we turned up the dial after the series A on our outbound efforts.
So we hired a BDR team, started out externally and then eventually brought that entire function in house.
And that helped to do some outreach to the accounts that we thought would be meaningful to us and start to educate the market and start to get meetings in the door that may have otherwise not been shopping for this.
So that expanded our reach for sure.
And then just continuing to get content out that was more thought leadership, content around how to unstuck yourself if you're stuck in the monolithic game and you are considering moving to something that's more composable.
And so that helped as well, because whether somebody was ready then or ready six months later, they remembered us because of the content that was out there.
So that's kind of how we started to build our pie a little bit.

Omer (27:07.830)
So inbound is great.
Obviously you get people, they know what the problem is, they're kind of reasonably educated about a solution, they're looking for a solution.
Conversation is a lot easier when you then move to demand gen and you're having to go and educate a market about the problems that they have and you know, blah, blah, blah, there's a whole set of new challenges that come along with that.
But also, instead of somebody coming to you and saying, hey, I'm interested in looking at your product, you've now got to figure out who to go and talk to in a company with thousands of employees.
And so I think you kind of, you described a Persona or the type of person that you go and look for.
But as you were kind of moving into this next stage of demand gen, how easy or hard was it to find those people in those companies?

Neha Sampat (28:02.280)
Pretty hard, honestly, because it was still pretty new.
Again, this was very much an early adopter product in the early days.
It's a lot easier now because people are looking for it.
So you can find titles and they've either heard of us or they've at least heard of the approach.
But at that time it was hard.
I think that the work that we did in that timeframe in 2019, 2020, really had an impact on who's coming to us now because they went over the hump of, okay, we are ready for a change.
And this is the company we've been learning from for the last couple years.
So it's an important seeding effort, regardless of how impactful it is to pipeline in the short term.
And then I'll add one more thing that became important at that time, which was starting to develop and build out the partner ecosystem as well.
Because for building something like this, you're either hiring the talent in house or you're working with an agency or a system integrator.
And even the agencies and system integrators that typically worked with the monoliths are on the learning track because they have to figure out, how do I continue to make, you know, if I can build something this quickly, how do I still make enough money doing it with something that's faster?
And that's, that's an ongoing challenge for innovation with, with those types of partners.
So just building out those relationships and the trust and, and figuring out ways to be the go to partner when those integration and agency partners are ready became really important too.

Omer (29:31.930)
So I think when I look at your story, it's, you identified the problem.
You initially built a very simple product, kind of kept improving it, switched from services to a product business, bootstrapped for first 11 years, profitable multiple seven figures, and then now where you are today, having raised $169 million.
The story sounds great in terms of, you know, growing.
And sure, we can look back at some of this and say, yeah, could you have done this earlier and grown faster here?
Or whatever, but generally, it's like, there's a lot of upside here.
But when it comes to growth, can you give me an example of like, you know, one of the struggles that you kind of experienced along the way, one of the hard things or a mistake that you made that kind of, you know, people listening to this can realize, hey, you know, yeah, we're talking about some of the accomplishments here, but there was a lot of crap to deal with along the way as well.

Neha Sampat (30:30.210)
You know, the hardest thing for me, and I'm a very empathetic leader, so to me, a lot of it is just about keeping people happy.
And that often means keeping employees happy, customers, keeping customers happy, and doing it in a way that's authentic.
And with employees, what I've learned, and still learning, is you kind of have to hire people that you're excited to work with, but that you're going to learn from.
And that feels super obvious.
But the reality is a lot of founders make the mistake of hiring someone they like more than someone that they, that will challenge them.
And, and I've.
What I've learned is that you kind of have to hire people that are, that have the experience at the stage you want to be at.
One to two years out, right?
Because they come in, they've seen it before, and they can help guide the company down that part of the journey.
And at a company of that's high growth like this, we change every six months.
So where I was six months ago is different than where I am now.
It's a different company.
We do things a little bit differently, we have to think differently, we have to act differently.
And also the market's shifting around us and all these other things are happening.
So what's hard is when you bring in someone who's super hardworking, busting their butt for you, really wants to be in it and does everything really well, but doesn't really know how to do it for the next stage.
It's really demotivating to them when you bring in someone over them that maybe has seen the scene before and that, you know, they will learn from if they're open to it and if they're willing to get the coaching.
But if you've been there from day one, you don't feel like you need the coaching or that, you know, you're.
You have that pride that I've taken the business from here to there, which they have.
And so that's been probably the hardest thing for me, both emotionally and rationally, just figuring out how to keep the people that I want to keep on the journey happy and engaged and motivated, even though it means we do have to bring in new people to help us get to the next stage.
And the most difficult thing about that is knowing when it might be time for them to go and do it again for another series seed to be company because that's what they're really good at.
And just being like super honest there, that's been probably the hardest thing I've dealt with.

Omer (32:43.670)
And what about yourself as a leader?
What do you do to help yourself prepare and evolve kind of for each stage?
I talked to Vishal Sunak, who's the co founder and CEO of Link Squares recently and when he started this business, he was the guy building the Ruby on Rails prototype to go and show to customers and try to land their first deal.
And.
And now the business is like, I think they raised about a similar amount to you that they're probably doing about 40 million in ARR.
And his job is completely different now, like, because there's these specialists, you know, and senior people all around him and.
And it's kind of like a similar thing where, you know, yeah, you have to kind of figure out how you're going to have the right people, but then you've also got to think about kind of looking at yourself and Saying how do I evolve?
But also how do I grow as a leader?
But then also how does my role change as a leader?
Because that keeps evolving as well, right?

Neha Sampat (33:50.790)
Absolutely.
Yeah.
And again, that goes back to every six months.
It's a little bit of a different company.
And so every six months I have to get in the mindset of I'm firing myself and then I'm re evaluating whether I'm the right person for the job.
And obviously I can't just exit every six months.
It's not that easy.
But just asking those questions and posing those questions to my coaches, my mentors, my investors, and hearing the hard feedback so I know where to spend my time for the following six months so I can grow into the next stage of the role.
And it really requires becoming very resilient.
Right.
Like you have to have a thick skin and you have to learn to take the hard feedback, but that just makes you a stronger and better leader for the next stage.
So for me, it's been a lot of that.
It's surrounding myself with people that are willing to have those hard conversations to help me grow.

Omer (34:42.520)
Yeah, I think someone said to me, everybody has a friend who tells you things that nobody else will and everybody needs that friend.
Right.
It's just like somebody who's going to kind of give you the harsh feedback that ultimately helps.
But sometimes whether you're going out and talking to customers and trying to get feedback on a product, people want to be nice and they want to help you and they want to say things that they think you want to hear.
And then even when you're looking for feedback in your own organization, it's like it's kind of tempered.
Right.
It's just like people aren't kind of giving you the full unfiltered feedback.
So yeah, I think that's super important in terms of having those people around you.
Let, let's talk about the kind of where the business has gone to today.
So we talked about like inbound demand gen and now I think a lot of the focus is on ABM account based marketing.
Again, like, tell me like what has that meant for the business in terms of how you operate and kind of find customers?

Neha Sampat (35:49.820)
Yeah, I mean it's kind of like the market and the product market fit and the propensity to buy has evolved as we've evolved.
Right.
So if you look at where the market was a year or two ago versus now, it was definitely more early adopters that were buying technology like ours.
And now you're starting to see it be like sort of early majority and more, more towards the mainstream.
And with that comes now like looking at the Fortune 1000 accounts, the target profiles within those accounts and what they're looking for and the pain points that they're facing and knowing that we can help bring value to them, starting to just pay attention from an account based marketing perspective and intent data so that we can give them the right tools and the right messaging when they're looking for it.
So it's not in a creepy way necessarily, but more in a way of being helpful and relevant to whatever challenges they're facing.

Omer (36:47.600)
Is that just like a part of what you're doing or is that like ABM is like the main thing that most of your team is focused on in terms of customer acquisition?

Neha Sampat (37:00.750)
It's a big part of it, but it's not the only thing.
And everything when you're doing a high growth acquisition like this is multi.
Threaded.
Right.
So there's definitely events, there's working with partners, there's just general networking.
But ABM and then just digital like you know, surrounding ABM and educational content, thought leadership content is also part of the game.
So it's just kind of what we've added since we've been doing all the other things.

Omer (37:29.480)
As you go from inbound to where you are today in terms of like abm, what does that do to your sales cycle in terms of how long it takes to, to close a deal, is that becoming longer and longer?

Neha Sampat (37:44.410)
It's really hard to answer that because some of the factors are so there's so many variables.
Right.
If the market remained exactly the same over the last few years, we would have a steady state of like, yes, ABM is making it go faster or slowing things down because now we're dealing with longer education cycles.
But we've had like from the beginning of COVID a major slowdown in buying anything because everyone was freaked out and didn't know what was going on.
To like a really speed sped up cycle because everyone's saying we have to do everything digital to like some normalizing in, in the last year to now there's some uncertainty in the market.
And so it's, I think market conditions drive sales velocity more than typically just the playbook.
But the playbook certainly helps speed things up if you do things right and you know how to bring value quickly and you know how to have the right conversations with the right people.
So it's a little bit hard to tell but you know, there's bits and pieces that help be, help you just continue to improve your sales efficiency as you learn more.

Omer (38:50.060)
Yeah, I think the last three years or so have just been so weird that, like, it's hard to make any sense of, like, you know, it's like.
Anyway, that's this conversation run of the day.
I want to wrap up.
We'll get onto the lightning round in a minute.
But when you look back at all the years that you've been running this business, if there's one thing that you could go back and change that you wish you had done differently, what would that be?

Neha Sampat (39:17.150)
Honestly, we've talked about already, but I would have raised capital sooner because I think we would have been further along.
Now.
It really wasn't because I was being stubborn and trying to not give up equity or anything.
I just didn't know better.
So I would have maybe gotten a better coach or mentor to help us make some decisions that were smart earlier on.

Omer (39:36.400)
Okay, so let's get on to 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?

Neha Sampat (39:46.160)
Yes.
Let's do it.

Omer (39:47.520)
All right.
What's one of the best pieces of business advice you've received?

Neha Sampat (39:50.800)
I was told that I should restructure my companies to improve the value of them, and that was what led to the split and the great restructure.

Omer (39:58.470)
Interesting.
What book would you recommend to our audience and why?

Neha Sampat (40:02.070)
I give every new member of my leadership team the High Growth Handbook by Elad Gill, and I recommend every startup founder should read it and just keep it as a reference bible on their desk.

Omer (40:14.550)
What's one attribute or characteristic in your mind of a successful founder?

Neha Sampat (40:19.430)
Resilience, by far.

Omer (40:21.270)
What's your favorite personal productivity tool or habit?

Neha Sampat (40:24.230)
It is Tuesdays at noon.
This started in San Francisco because there was a foghorn that was like the emergency testing system, and now I have a foghorn on my phone.
I live in Austin now, so I have to do it on my phone.
And it is my moment to take a deep breath, release all things bad and negative and retain all things good and positive and move forward.

Omer (40:46.230)
That's Tuesdays at noon.

Neha Sampat (40:48.390)
Tuesdays at noon.

Omer (40:51.920)
What's the new or crazy business idea you'd love to pursue if you had the extra time?

Neha Sampat (40:55.120)
I've always wanted to build a personal CRM for super networkers that lets you keep track of people you meet when you met them last, and their kids names and their favorite things.
There's nothing like that out there, as far as I know.

Omer (41:10.320)
What's an interesting little fun fact about you that most people don't know.

Neha Sampat (41:14.160)
I am a certified sommelier, so wine as a hobby is a big part of my life and my side hustle.

Omer (41:21.170)
What does it mean being certified?

Neha Sampat (41:23.170)
It means that I've gone through the court of master Sommeliers and passed their certification, which is an all day long exam that I personally took two years to study for.

Omer (41:33.170)
Wow.
And finally, what's one of your most important passions outside of your work?

Neha Sampat (41:38.210)
It's kind of related to my work because I brought it in, but it's really advocacy for girls, women, underrepresented minorities in the tech field or just in general.
And I support a lot of organizations that do things to support that.
I sit on some related boards.
I'm the owner of Austin Woman magazine trying to uplift women in Austin.
So a lot of things related to females and advocacy for females.

Omer (42:00.970)
Love it.
Awesome.
Neha, thank you so much for joining me and sharing the story of Content Stack.
I know when you've been working on a business for so many years, it's hard to try to distill that story down into, you know, the 45 minutes or so that we had.
So I appreciate you pulling, pulling, you know, those, those memories out and, and kind of helping us understand like the journey and also, you know, some of the decisions you made along the way and why you did what you did.
And I appreciate, you know, your candor and, and some of the answers that you gave, like, hey, you know, I didn't raise money because I didn't know any better.
You know, that's, I think that's a great answer.
So.
But I appreciate you making the time and, you know, sharing your experience.
If people want to check out Content Stack, they can go to contentstack.com and if folks want to get in touch with you, what's the best way for them to do that?

Neha Sampat (42:56.540)
You can reach me on LinkedIn.
That's probably where I'm most active.
Or on Twitter.
I'm at NEHA sf like San Francisco.

Omer (43:04.170)
Sweet.
We'll include a link to both of those in the show notes.
Thank you so much and I wish you and the team the best of success.

Neha Sampat (43:10.170)
Thanks so much.
Great to meet you and thanks for having me on.

Omer (43:12.650)
My pleasure.