Beyond Product-led Growth: 7 Lessons Learned in Product-Led Scaling with Dropbox GM Rachel Wolan

Thank you. It is so great to be here today at SAS Dirt, seeing all of you, IRL, 3D, all the things. I'm really excited to talk to you today.

I'm going to walk through 7 lessons, hard-earned lessons that I've learned in what I call product-led scaling. It's kind of what happens after product-led growth. And I'll talk to you a little bit about my experience at TalkDesk, a little bit of my experience at LiveRamp, and now at Dropbox. But first, I want to tell you a quick story. So that's me. And this is what I call my pandemic hobby. I really enjoy stand-up paddleboarding. And I'm stand-up paddleboarding in what is called the Sissons Slough. Try saying that like 3 times fast.

It's impossible.

And what is unique about the Suisun Slough is that it is a freshwater body, but I'll just kind of place it for you. It is sitting kind of near Benicia. So for those of you who aren't Bay Area natives, the Bay Area is surrounded by water. This is something I learned over time from Chicago. And the Suisun Slough meets the Grizzly Bay, which is a saltwater body, which meets the Carquinez Strait, which meets San Paulo Bay, and eventually the San Francisco Bay. Those are all saltwater bodies. And what's unique about the water in the Suisun Slough is it's what's called brackish water. Now, that sounds really gross, but really all it is is a unique ecological phenomenon where saltwater and freshwater meet, and virtually nothing actually survives in there. But as I was, like, paddling around and kind of looking around, I noticed— these little turtles swimming around. And those turtles got there because some parent was like at a fairground and some kid won a turtle and, you know, the parent wasn't so happy, they dropped that turtle into the stream, and the turtles, you know, this is how turtles have survived for the last 20 million years. But what is unique about the Suisun Slough is that There are climate scientists at the University of California at Davis who believe that turtles hold the key to potentially understanding global warming. These turtles have managed to thrive in an environment that literally nothing else is able to live in. And that's a little bit like— product-led scaling.

What's unique about product-led scaling is you're dealing with, you know, most companies, like what I call the product-led grown-ups.

How many of you actually work for one of these product-led grown-ups? Raise your hand. Okay, we've got like a few of you in the audience. So what's unique about product-led grown-ups is that they have managed to take a product-led motion and marry it with some kind of sales assist or sales-led motion. Now, what I think is interesting about this, you know, working at one of the product-led grown-ups, is it seems so straightforward. You know, I worked for the original product-led growth company, Dropbox. And being on the inside, you start to realize, you know, you actually kind of need both motions. You need to find a way that both motions work together. So that's what we're going to talk about today. How to actually navigate your way through the product-led maze. Now, I have worked at a wide variety of different types of companies at different stages. I worked at Talkdesk, which is one of Jason's favorite investments. It's one of the latest decacorns. I worked there when we were going from $1 million in ARR to around $50 million in ARR. I ran product. Then I went to LiveRamp. I ran product at LiveRamp. For those of you who don't know LiveRamp, it is in the paid media marketing space.

It's a public company.

And we help marketers take their CRM and then go and target on the—

sorry, on paid media. And then, of course, you all know Dropbox. I joined Dropbox about a year ago. And we're kind of in that— we're still in that maze. And so first, The first lesson that I'd like to share is what I call improving your customer's customer's CSAT. So what does that mean? Well, I like to kind of start this with a story. So I joined Talkdesk, and about a month in, I was about to fly to Portugal. And Portugal is where most of the development team was at the time. And what I, you know, I was about to get on the plane, and Tiago, our CEO, calls me and says, You're not going to Portugal right now. You're going to Atlanta. And we had an outage last night for 2 minutes, and you're going to go and talk to our largest customer, which was the Weather Channel at the time. So I get in the plane, and I fly to Atlanta. And I get there, and the Weather Channel— how many of you have ever watched the Weather Channel? OK, everyone, probably everyone. That's actually not what the Weather Channel is for the most part. That's not where they make most of their money. They make most of their money powering the weather app on your iPhone. They power also like what are kind of like Bloomberg terminals inside of airplanes. And when TalkDesk went out for 2 minutes, pilots were actually trying to call down to the weather channel into the— what I would only describe as like— I've never been on the floor of NASA, but it's almost like a NASA control center. When TalkDesk went out, the pilots weren't able to say, "Oh, should I fly through this fog or fly around it?" And so we really, you know, that was kind of like the first lesson that hit me where I was like, "Oh my God, we're actually not building for our customer. We're building for their customer who is paying them." And we are one of these mission-critical systems. And so we really made it our mission in those early days to make it super easy for agents to self-serve onboard themselves. We made it easy. You know, we called it— I think this is like the dirty little secret of all SaaS. It's on the front page of every single web page. It's the hero. So ours at the time was called Create a Call Center in 5 Minutes. Guess what? No one is creating a call center in 5 minutes, but it made it seem easy. It made it seem accessible so that anyone could do it themselves. And so at that time, we also did something really unique. We started doing— it doesn't sound crazy right now, but at the time, we started doing SMS CSAT and making it super easy to collect data that way. We also allowed— and this is kind of one of the unique things. I'll give credit to our designer. I think this is like a design hackathon. We actually gave the agents the ability to say this is how happy my customer was at the end of the call. So we very intentionally started laying the groundwork for being really a data asset. And so lesson number 1: improve your customers' customers' CSAT. So here we are. TalkDesk has survived going from $1 million to $10 million, which As many of you out there know, it's not easy. And now we're at the point where we're like, OK, let's put our foot on the gas. How do we actually, like, 10x this thing? And as we looked around at what options we had, we had something like 20 different integrations that were actually driving revenue. And really, all that mattered was one of those integrations, and it was Salesforce. And the reason why it mattered is— something that every single time our customers kind of hit a certain level in their own growth, they graduated off of whatever ticketing system they were using onto Salesforce. And we saw this pattern happen over and over and over again. And why, why was that interesting? Because Salesforce is notorious. It's hard to actually like navigate your way through that ecosystem. And what we did that was different, well, first we got to know the product team at Salesforce really well. We would, like, go out to beers with them on a regular basis. But what we learned was we kind of treated them almost as our customer. And we started to learn about the customer journey across companies. And we really started to focus on, how do we, like, actually land with a product-led partnership? So we built the first— kind of onboarding flow directly through Salesforce so that the sales engineers at Salesforce could create a call center in 5 minutes on Salesforce. This is the first time that happened. And so really starting to think about, okay, what part— which customer are you solving this for? And how do you actually create a product-led partnership, not just a product-led product? And so we really kind of crafted this motion and then also started to expand into outbound sales. So we went from, you know, these are the use cases on the bottom. We went from call center in 5 minutes. Now you can actually like add outbound sales. And oh, by the way, now we're actually starting to land mid-market accounts on a more regular basis. Land with product-led partnerships. Next. Now we're at the point where things are going crazy. We're adding more and more customers. We're also losing customers, and we don't always know exactly why we're losing customers, but we see customers graduating off of us onto the Five9, the Genesys of the world, and we realize we actually, we can't build fast enough. So, you know, our kind of white lie at the time was intelligent contact center, We had one AI engineer at the company, but we really wanted to be this AI-powered call center. So how do you do that? You actually launch a platform yourself. And so what we did was we built a product-led platform ourselves. We kind of, we were looking at like Heroku and Salesforce for inspiration. Highly recommend going through the Heroku flows to see how they allow you to add licenses. We require that every single partner that wanted to be in the Talkdesk ecosystem set up a trial themselves. So this was like kind of unheard of in this industry where, you know, these sales cycles took 3 to 6 to 9 months. And we were saying, no, actually, any admin or any supervisor can go and add a trial themselves. We also launched a wall-to-wall workflow added a desk phone at this point so that we can start to creep our way into enterprise. And ultimately, we identified a target where we ended up acquiring one of the, the analytics platforms. So you can kind of start to see there's a lot of different ways that product-led motions can get layered into a sales-led motion. So let's switch gears a little bit. I'm going to tell you a little bit about my time at LiveRamp. So I helped LiveRamp shift from, you know, about $100 million and grow into about a $400 million business. And what was unique about LiveRamp is we were really, truly sales-led. We were really focused on mid-market, and we were also kind of in a pickle. LiveRamp, is for those of you who don't know, as I mentioned, you take your CRM, you run it through LiveRamp, and then we basically maintained a cookie graph so that you could go and target anywhere on the web. But what we had learned is that Google was getting rid of cookies. So we were like, oh, something, I can't stay on stage. And what we did next was kind of look around our business and say, okay, what is resistant to cookies? And what we realized is that our TV business was really focused on, you know, it was growing like crazy. And we saw this little partner called Data+Math that was kind of like trying to, you know, they were getting more customers than we were in the TV space, which is crazy. And what they had done was kind of build their own data asset. They were able to, in a matter of days, days, get somebody up and running doing television measurement. This is like unheard of at the time. And so I think this is the fastest acquisition I've ever been part of. We acquired them in, I think, 3 weeks. And all of a sudden we had a product-led motion that was like driving a bunch of our sales-led motions at LiveRamp. So really think about and kind of look at your business when your back is against the wall. Think about, well, is there somebody I could go and acquire that would actually give me that product-led motion? So again, understand your customers, do something about it. We weren't quite ready to do something about it, but by making this acquisition, we were going down that path. So here I am, I'm, you know, maybe I'd been there for 6, 8 months, and I went and met one of our customers. And I was in a boutique retailer in Minnesota. And this retailer really wanted to have us meet with their data science team. And I was like, well, we've got all these out-of-the-box solutions. And you guys are already buying this from us. Why would we go meet with them? They're like, no, no, no, trust us. So we sit down with their data science team. And the data science team says, that's great. You took a load off of us by giving us access to these insights. But we just kind of want the data. We were like, I don't know.

This is licensed in a particular way.

And what we realized was there's a huge opportunity in the analytics space that was being unmet. And we were able to go and build a product-led motion for the data scientists. We were able to create a closed-loop environment where we put the data in. Data scientists were able to use the tools they were already used to, like GCP and BigQuery. And we created something that we called the safe haven, where your data goes in, but your data never comes out. We were able to use our own IP to create this new environment, but then we, what was unique about it and why I call it a product-led motion is data scientists were creating analytics and publishing them to the marketers, publishing them to the sales team, publishing them all across the organization. So really think about it. If you're working for a sales-led company, what are ways that I can actually use product-led techniques to expand within the organization I've already landed. All right, so here we are to where I am today. How many of you in the audience have a Dropbox account? All right, so this is probably like one of the first companies that I'm talking about that you've heard of. Awesome. So Dropbox, as I mentioned, one of the first true product-led growth companies. I remember 2010, I sent an email to about 50 people saying, hey, do you want 2 gigs of space? That was a lot back then. And I think I collected maybe 15 gigs for myself off of that growth hack. So one of the original value props for Dropbox was really around storage. But when I joined Dropbox, you know, a year ago, storage is commoditized. Storage is kind of like we have to have it, but that's not the reason why people use us.

And so I was really trying to wrap my head around this as I joined Dropbox.

I went and I sat down with like 30 customers being like, well, why do you use Dropbox if you also pay for Google, or you also pay for Microsoft, or you also pay to pay for whatever. And what I learned, I think it was one of those things you kind of have to come in as an outsider and really have beginner brain to something, because the reason why people were buying us was slightly different. They were buying us because we made it easy to share content outside of Dropbox. And what was unique about that is Dropbox, like the original, reason why people use us was you have an iPhone and you have a PC and you wanna like access all your files between those two. Well, now it like kind of shifted. Well, I have a PC and I'm sharing a file with you and my client is on a Mac and I wanna make sure they can actually open it. So somewhere along the way, our value proposition had completely shifted, but we had kind of like growth hacked our way from, you know, like Dropbox was the fastest company to go from zero to a billion dollars. We were not the fastest company to go from a billion to $2 billion. But what was interesting about it is, you know, it was like kind of a straightforward path to a billion, but a billion to $2 billion was not straightforward. We tried to go to mid-market with a sales assist motion. We tried to go to enterprise with a sales Sales led motion. We tried to add a new company. We bought HelloSign. But really, ultimately, people are, you know, our value prop had evolved, not completely changed. And so this year, one of the things that we've really been focusing on, you know, our website doesn't say it just works, but internally that's kind of like our motto. Like, it just better work. We really focused on how do we really just start to improve our funnel health and really kind of go back to the basics, improve retention, pull out some of the growth hacks. It's really hard to pull out growth hacks once you put them in. And just, I call it giving before you get, really focusing on that basic first user experience. So as you start to, like, come into a new company, think about where they are in their trajectory and really try to put on that beginner brain. Or even with yourself, like, why are your customers using you? What has changed in the market? And how do you continue to lean into that, you know, that change? So evolve towards value from virality. And finally, so we found our next wave to ride. And it wasn't the easiest thing when I started. It wasn't obvious. But what's unique about Dropbox is that, you know, maybe this is not unique about Dropbox, but I think during COVID everything changed, and including our most engaged users' workflows. So our most engaged users are So the creatives, freelancers, creative teams, people using big files, right? They're using big videos, and it's like The Chainsmokers sharing content, or whatever. So what's unique about Dropbox is we have all these amazing creators on our platform. And we're in this just completely different environment now. Where we've— are able to actually tie together workflows, simplify things. But the other thing that's unique is we're in this era transitioning from the file to the cloud. And what we believe is the next era for Dropbox is one organized place for all of your content. So the last thing I'll leave you with is if you're building for everybody, sometimes you end up building for nobody. So make sure you understand who your best users are at scale. So last 3, kind of wrap up here. Make sure that you understand how your product-led motion is evolving. You're kind of paying attention to those transitions because those transition points are where the opportunity sits. Make sure you don't try to box product-led anything into anywhere. And then finally, figure out how to marry your sales motion with your product-led motion so that you can survive, thrive, and evolve like the turtles. Thank you so much.