Dive Deep Into Go-to-Market Strategy With Webflow CTO Bryant Chou

Michael:

Welcome to Crossing the Enterprise Chasm, a podcast about software startups and their journey moving up market to serving enterprise customers. I'm your host, Michael Grinich. I'm the founder of Work OS, which is a platform that helps developers quickly shift common enterprise features like single sign-on. On this podcast, you'll hear directly from founders, product leaders and early stage operators who have navigated building great products for enterprise customers. In every episode, you'll find strategies, tactics, and real-world advice for ways to make your app enterprise ready and take your business to the next level.

Today I'm joined by Bryant Chou, the co-founder and CTO of Webflow. For those of you unfamiliar, Webflow provides a platform to designers and companies looking to make professional custom websites without requiring them to write any code. In 2020, Webflow is working with over a 100 000 active customers. And in January of this year, they actually became a unicorn raising $140 million at over a $2 billion valuation. At that time Webflow was making about 5% of its revenue from enterprise forecasting to grow that by a factor of 10. A fun fact, WorkOS website is actually one of those customers of Webflow enterprise. And I'm super excited to chat with Bryant about how Webflow is moving up market and crossing the enterprise chasm. Bryant, welcome to the podcast.

Bryant):

Hey Michael, thanks for having me. Excited to be here.

Michael:

So let's dive in. Give us a quick update on Webflow? Where's the business and team out today, and what's your current focus?

Bryan:

So we're about 320 full-time employees spread out across the world of remote first and we have a growing sales and marketing team. I think we have close to 15 reps right now on the sales side. Marketing's also organization close to 30. A lot of my focus now is really as a non-CEO co-founder just making sure the broader team has all the context that I have so that they can do their jobs in the best possible way.

So just trying to relay as much of my experience first with the technology, building the core product, and then also a lot of my experience trying to find product market fit in the initial days and all of the learnings that I have had working very closely with customers. So I technically still run some organizations, but more and more of my focus now is making sure that the right folks and the right leaders have the context they need to succeed.

Michael:

So Webflow today is being used already by a bunch of large companies and large brands. I want to turn back the clock a bit. Let's go back to those earlier days when you were still trying to build the product, get to product market fit. How did enterprise factor into your thoughts around that time? Did you always know that this was going to be something you would do? And maybe if things changed, when did they change for you?

Bryant:

Yeah, so we had a bit of a roundabout journey with enterprise. The funny story is, is that when we're still in YC, we got so much advice. And one of the bits of advice that we had was, "Hey, Webflow is way too difficult to use, you guys should think about going down market." "Hey, look at what Squarespace is doing, you guys should just build another Squarespace." And for us, it was just never really in the vision of the founders to just do what another company did. What we really tried to focus on is we saw that there was just a gap between designers and developers.

So we knew that we wanted to create a product to directly address that gap. And when it came to the go-to market, it was actually very difficult because essentially the first personas that we're focused on where these broke freelancers or small agencies. And despite the fact that they had very little willingness to pay and they didn't have a lot of disposable income. We just felt like we needed to figure out how to build a product for the most disenfranchised personas that were building websites.

So we actually slugged it out and built that product for this audience that no one cared about because there's just a very, very little market there. But over time, maybe five years in, we started to realize that these freelancers, these designers, they would go on to find jobs at larger companies. And these larger companies would have the same exact need of building a bespoke professional website. And Webflow was the best possible choice for these companies.

So we started to actually take a step back and look at our overall customer segmentation. And we actually found that 50% of our customers were these freelancers, but the other 50% were these larger companies. And we're just, wow. We had no idea that our product was getting picked up by companies with 300, 400, 500 people full-time employees. So that's around when we started to think through, okay, what does it look like for us to go up market. And kind of kicked off a series of events to help us transition our business in that direction.

Michael:

What was the first thing you went after? And was there a breakout moment when you were, "Oh, this is a real opportunity. We really need to go after this." Was there a specific customer or a specific feature? Walk us back through those early days?

Bryant:

Yes. I'll share a story actually. So I think it was three days before Christmas in 2018 or 2019, I forgot. And I was visiting family in Stockholm and it was 9:00 PM. We just wrapped up dinner. It wasn't Christmas dinner, but I get a email from the head of digital, of a bank in Australia. And he's just, "Bryant, I really want to talk on the phone. We're dying to use Webflow here, but there's just a few things that I really need Webflow to do."

I hop on the phone just, "Hey look, we're about to roll out Webflow, but we really need some SLAs, we really need a MSA. We need commercial agreements in place so that my bosses won't look at me and just be, "Hey, what's going on here? Why do we not have these contractual agreements in place for such a crucial aspect of our technology?" And that's when the light really went off in my head. Because until that point we were a hundred percent self-serve which meant that you had to just essentially, the only way to pay for a product is through a credit card.

The only agreement that you agreed to was this passive terms of service. But this light went off in my head and it was just screaming at me that there were just so many customers that we're leaving behind simply because we didn't have a motion to usher them through to success. And that motion was the sales motion specifically. Because to that point, we thought everyone could buy through a credit card, but that's just not simply the case.

Michael:

Was the product the same for those folks? Were they requiring something different or was it literally just, "Hey, we need different paperwork."

Bryant:

Initially, the first batch of customers, it was agreements. So we did have some product distinction. A lot of it were the three S's, security, scalability, and service. And that's what they were looking for. So one of the first things that we had to build in the product was single sign-on and that became our very first point of product differentiation.

Michael:

And for people listening just for full disclosure, Webflow is a customer of WorkOS. We've been working together for, I guess, coming up on a year or so. You built the sales team at Webflow as well. I remember in one of our previous conversations, you kind of led the initial development of the go-to-market team. Can you talk through how sales looked early on, maybe those first few reps and how you structure the motion in the very initial days. Not necessarily where you ended up today, but in those early days.

Bryant:

I can't state claim on me building the initial sales team. What I can say is that I definitely led efforts to experiments with this motion. And what I did was I looked actually at our support organization. And because our support organization and our customer support organization, they're handling thousands of emails every single day from our customers. And I knew that they were very in tuned to our product. And they're also very in tune to the different kinds of customers that we would interface with.

I was very intentional about finding a customer support person to essentially just trial a sales motion. So I found someone that had some sales background before Webflow, was very eager to kind of expand his skillset. And was also very willing to kind of thrive in the ambiguity, which comes from a lack of an organization, a lack of goals. And it was kind of early days start up again, where instead of you're trying to find a product market fit, you're trying to find a go to market motion fit.

And finding that go to market motion fits was definitely not easy. Because for us, we're the founders, none of the founders have B2B SAS backgrounds. None of the founders have pure sales background. It was a lot of trial and error. So what we did do eventually was that we had this one rep essentially try and close our first six or seven accounts. And at that point based off of the success of that, we went in and brought in, our now VP of sales and customer success, Kai. And he's the one that really has been scaling the team to where it's at today.

Michael:

This is actually something pretty common I've heard from a lot of companies that early sales grows out of some customer success motion, I guess, just because those folks are closest to the customer early on.

Bryant:

Yeah, that's right. And not only that, depending on where these support people sit, they also have a really good sense for where the product is limited. So they will actually be able to provide very high signal on what are the right initial customers we should go after. So for example, if we knew that selling to FinTech or Pfizer insurance companies involved a bunch of security questionnaires or certain product features, the support people, they would already know that.

Because they've already fielded probably 10 to 15 different emails from these companies asking for these features. So finding that partner there has been crucial and it's really helped us sequence the right product roadmap, it's really helped us sequence the right type of targeting for companies. Because in the early days, it's all about the dialogue that you want to have back with product, back with marketing, to help you zero in on where the go-to market fit is.

Michael:

Do these enterprise users come from a different channel. I know that Webflow early on had really tremendous word of mouth and bottom-up growth, I think across that kind of freelancer stuff that you mentioned. But these bigger brands are totally different. Where does the growth come from today for these enterprise customers? Can you track that back to a source?

Bryan:

Yeah. Yeah, for sure. We still have a very strong organic motion. Our word of mouth is still thankfully just very productive for us. But the thing is, is that with these larger established companies, many companies are just accustomed to the tools that they've been using for years. So a thing that we have to focus on and a muscle that we have to build are two things. We have to build a marketing motion that can attract new customer logos, where there isn't necessarily a product champion already in-house. Which means that we have to be very focused on who we message to and what our position is to for example, different heads of marketing, heads of digitals.

We have to have almost a different type of talk track because our end product personas are very different than the decision-makers and enterprise company. So that's something that we have to do. And then on the second part, our enterprise team and our reps, they also have to be quite plugged in to what the eventual product roadmap is going to be. We have to be really laser focused on what we sequence. For example, we don't want to over-rotate into the enterprise, right? That's a common thing that people talk about. So we actually have to figure out how do we want to move enterprise features forward while still making progress on features that all customers can benefit from.

Michael:

You had mentioned early on about how those first few deals were kind of just putting it on different paperwork in a way, same product, same experience, just people saying, "Hey, we need a different commercial agreement." How has that evolved today in terms of the selling motion? Is it more complex, is it totally different similar to the self-serve motion? Kind of walk us through the similarities and differences between those?

Bryant:

So I would say today it still hasn't evolved too much from where we started. So really it's three S's, right? Security, scalability, and service. Very important thing though, that we discovered was that our initial beachhead in this market with these freelancers and agencies, they became extremely important partners in our upmarket motion. So this co-sell motion that we now have with our, what we call enterprise partners has become pivotal to our success, where we really lean on the expertise of our enterprise partners, their intimacy with our product.

And then also, sometimes they even have better client relations than us. Because if you're a buyer of an enterprise IT software, human psychology kind of trains us to trust the neutral third party, as opposed to the person that's trying to pedal the good or service. So of course, our reps are very straightforward and we try to establish that very close relationship with all of our accounts, but it's different because they're a employee of Webflow.

The buyers of the software know that they have quota. But these partners, they're more or less neutral. And that's a very powerful person to have at the negotiation table, at the selling table. Because they really help us communicate the value of Webflow's platform from a neutral voice. And that becomes something that has shown not just helpful in terms of helping us close deals, but also helping us grow accounts over time. So they've been helpful in us expansion as well because they start to educate our customers on where they can be using Webflow more and more

Michael:

That sounds like kind of a variation of the internal champion, which people often talk about, but it's slightly different, right?

Bryant:

Yeah. It is slightly different. So oftentimes we still will have that internal champion, but in this case, it's like having the consumer reports version of B2B SAS software, where you know that the information you're going to get from a potential partner to make your purchase successful is going to be rooted. I mean, there's mutual success there.

Because a partner would not be championing your product unless they knew that they could bring it to the finish line in a cost effective way and it's going to provide an excellent customer experience. So that actually provides a lot of validation just in the same way that if you were to look up what car to buy. Consumer reports hopefully has a fairly non-biased point of view on what the best car is.

Michael:

That authentic persona, it sounds like or that authentic viewpoint really drives it forward. This seems to be pretty common across all these kinds of product like growth type of companies, where the product experience itself is really what shines through and carries through the sales motion versus a sales rep slamming the table, or giving discounts or something like that.

I wanted to also ask about how the Webflow product has changed. So recently-ish, you announced some new features in Webflow, including things around roles and permissions. Plus there's some brand new features around kind of multiplayer collaboration, multiple people editing. Definitely seem pretty useful for teams and bigger organizations. Can you talk through where these features came from, how you prioritize them, maybe how you discovered these things to build?

Bryant:

Yeah. For something like roles and permissions, it had always been something in the back of our minds that we knew we needed to beef up. Because there's a bunch of features in Webflow that got us to where we are. And those features are things that really are features that have never been built before, such as turning Flexbox into something that only developers could use into something that no code visual developers can use to build really bespoke and interesting web layouts, things like interactions, right?

Things that used to take a JavaScript developer weeks to do something that now someone in Webflow could do in a matter of hours. So for something like roles and permissions to get prioritized, it actually required us to build a new muscle in our product strategy, which is how do we start to think about the different stakeholders in the web design process and build products and features to serve them.

And it was no longer about the end designer product user, because now we've solved so many of their problems, it's gotten to the point where people in their periphery are starting to struggle actually using the product. So roles and permissions is actually meant for the site administrator or the content person in the company or marketers to make sure that they have the right access to the Webflow project that doesn't step on the designers toes, to make sure that the overall workflow of working on Webflow is a cohesive experience that factors in all the different stakeholders of the web design process.

And things like polite handover, roles and permissions, it's really been, not a rude awakening, but this realization that we had, that we need to start thinking about building a product muscle to think beyond the core designer persona. Because we know that in order for Webflow to truly be successful inside of companies, large and small, that we need to think about those other stakeholders.

Michael:

Yeah. And they are pretty different, different stakeholders with different needs, for sure. I want to reflect back. A couple more questions for you before we wrap up. Reflecting back on the last couple years as Webflow's really grown up market across the spectrum, what has surprised you as you've gone up market and looked at the enterprise? Thinking back, what was unexpected or what was surprising along the way?

Bryan:

I think one thing that I've reflected on is that you really need a robust go to market motion to make your upmarket motion successful. It's not something that you can tippie toe into. And it's something that the entire organization needs to rally behind. So that has stuck out to me because the kind of investment needed to make this motion successful. So I mean, customer success, not just the reps, but customer success, onboarding specialists. You'll have solutions engineers, you'll have a partner motion that I just mentioned. And then you have a marketing orientation to help with the sales motion. All of these things require a careful coordination.

And of course, early stage founders and operators can hack something together like we did, but I would definitely recommend that the moment you sense that there is true opportunity commercially, where you feel like the ACVs are adding up, where you feel like you can make this maybe not ROI positive in nine months, but in 18 months, that's a actual signal that founders and operators should really latch on to for, "Okay. Now it's time to go. Now it's time to staff up our teams. Now it's time to hire the support organization we need." That's been something that we've mostly gotten right, I would like to think. But then at the same time, I feel like we could have accelerated things a little bit more to build into supporting foundations for this motion.

Michael:

Last question for you, sort of along those lines as well. What advice would you give founders of a early stage company right about to go up market? Trying to think about this, maybe right at that breakout moment, right about to cross the enterprise chasm, what advice would you give?

Bryant:

I think all the advice is very circumstantial, but the one thing that Webflow has done well is make sure that we have true product market fit. Because if you don't actually validate that your product is beloved by end product users and it's driving real tangible business value. And your hearing the market feedback, the customer feedback, and it's just something that actually keeps you going. And it's something that you want to put up on your company all hands and say, "This is what customers are saying about us."

If you don't have that, if you have any sort of qualms about how sticky your product is and how valuable it is, it may be too early to think about going up market. And I would be thinking through how to potentially validate or tweak the product in a way so that you start to sense that really, really strong signal. Because sales is very difficult, and building a sales team that is trying to sell a product that doesn't have that market or customer feedback that's overwhelmingly positive and sales people are really excited to sell, that's a difficult place to be in.

Then it starts to feel like a slog. Then it starts to feel like the sales team members are really just trying their best to hit their quota. And then the culture starts to erode. And then all these detrimental dominoes start to really fall. And it puts a founder in a really precarious situation. Because then you've already invested in a sales motion. You're sort of left with very few ammo to retool. So think about your product roadmap to invest in the right places, because you can't have salespeople that have a quota where they just can't attain. And that's just going to be a sticky situation for everyone involved.

Michael:

Yep. There's nothing like product market fit for startups. I think this is a great place to wrap up. Bryant, thanks so much for joining us. Really excited to continue to see Webflow grow across the enterprise chasm and beyond.

Bryant:

Thanks, Michael.

Michael:

You just listened to crossing the enterprise chasm, a podcast about software startups and their journey moving up market to serving enterprise customer. Want to learn more about becoming enterprise ready? The WorkOS blog is full of tons of articles and guides outlining best practices for adding features like single sign on, skim provisioning and more to your app. Also, make sure to subscribe to this podcast so you're first to hear about new episodes with more founders and product leads of fast growing startups. I'm Michael Grinich, founder of WorkOS. thanks so much for listening and see you next time.