Attentive’s Brian Long explains the importance of talking to your customers

Eniac’s Hadley Harris didn’t mince words when he (virtually) welcomed Attentive co-founder and CEO Brian Long to our Annual General Meeting. In Hadley’s words, Attentive is “the most exciting venture-backed startup anywhere right now.”

You might dismiss such praise as hyperbole from an excited Attentive investor (and Eniac also backed in Brian’s previous startup, TapCommerce, which was acquired by Twitter for $100 million). But as Hadley noted, the startup now has more than 3,000 clients, having grown its customer base by over 270% last year. And it just raised a $470 million Series E.

So the conversation gave Hadley and Brian a chance to talk about Attentive’s journey, the challenges Brian’s faced along the way, and the tips he has for new founders. Here are some highlights.

Brian Long on finding product-market fit: “I think that when you have an idea for a business, you get excited, and you want to start scaling that and pushing that and building that as the entrepreneur. I think it’s important to also separate that excitement from the metrics, your goals and how you’re really doing, and taking a critical eye to how things are going. For us, we started out with the idea of messaging in text, but we were going to use it for communication inside of a workforce, as well as communicating with customers. I did over 100 demos of that product, and the communication with customers was what was clearly resonating the most, so that’s really where we decided to focus our business.”

On maintaining a sense of community while growing the team 4x during COVID: “We try to over-communicate. We were doing weekly all-hands for a long time, now we do them biweekly. I send out a lot of messages to the team about things that are going on. We have someone who sends out basically department-level updates on everything happening in each department to the entire company as like a three page summary every week. We also have an internal events person that’s been running events across divisions and teams, and doing all sorts of virtual events and virtual meetups and random coffees.”

On his advice for founders: “I think that you can’t spend too much time talking to your customers, whether that is a business like ours, that’s selling to other businesses and selling SaaS software, or if you’ve got a consumer-facing product, whatever it might be, whatever vertical it is, I think you’ve got to find your customers and you’ve just got to talk to them and continue to get their feedback and learning what they want. Especially customers that are more wanting to innovate and pushing to innovate and on the cutting edge, that’s really, for us, helped shape our product roadmap, what we do, what we hear, all that sort of stuff […] Where I’ve seen businesses run into issues at the earliest stage is when they spend a lot of time building, but not enough time pitching that product and really getting it.”

On raising money from Eniac again: “I recall sitting down with my co-founders, and we looked at all the different offers we had, and we said, ‘Why are we going to make this harder to ourself? Why take risk and work with folks that we haven’t worked with before and don’t know? We already love the people we worked with before, and it’s a great opportunity to just do that again.’ I would add to that we didn’t decide to work with everyone that we had worked with before, because we didn’t have the best experience with everyone. But we had a really fantastic experience with Eniac, and that’s why we chose to partner again.”

You can watch the full video above and read a lightly edited transcript of the conversation below. Also, check out our conversation with NYC mayoral candidate Andrew Yang from the same AGM, and we’ll be posting the video of our founder panel on product-market fit in a few days.

Hadley Harris: Hi everyone. My name is Hadley Harris, co-founder of Eniac. I’d like to give a special welcome to the Eniac LPs out there, as well as members of the broader community who are joining us. Thanks for coming today. I have quite a treat for you today. I have Brian Long, the co-founder and CEO of Attentive. We’re really fortunate to have gotten to work with Brian twice now. First, with his first company, TapCommerce, where we were the first investor and board member, and that sold for $100 million after the Series A. And then again, with Attentive.

A couple of data points on Attentive. In just less than five years, they have over 3,000 customers, they grew their customer base by over 270% last year, they just raised a $470 million Series E, and they burned less than $100 million in their whole time. And then probably most importantly, they drive 18.5% of their customers’ total online revenue via messaging. I’m definitely biased, but I think Attentive is the most exciting venture-backed startup anywhere right now. So really excited to have him. Brian, thank you for joining us.

Brian Long: Hadley, thanks for having me on. LPs, thanks for your initial confidence in us. We’re thrilled to have you be part of this journey, and we’re really excited about where things are going.

So, for the folks out there that don’t know much about Attentive, what do you guys do?

The vision for the company is to be able to change the way that businesses are communicating with consumers. We think that consumers in the next three to five years are going to expect real-time, personalized, two-way communication via messaging. So we’ve built out a platform to enable text-based messaging that starts at the top of the funnel with marketing messages, but it gets more tailored with very personalized messages and gives updates on everything, from when a product is shipped, to making a purchase, to customer service. As we continue to build intelligence onto that platform, we think this offers a great experience for the consumer, but also a must-have for any B2C business, really.

Having gotten to work with you now for eight or nine years, I think one of your superpowers is really understanding what the market needs in crafting a product to fit that need. If you go back to the very early days of Attentive — or what was then known as Franklin — you guys were trying a couple of different things, one of which was what became Attentive. Take us back to that process and how you were you able to go from that experimental phase to finding the clear product-market fit that you guys obviously found.

It’s a good question. I think that when you have an idea for a business, you get excited, and you want to start scaling that and pushing that and building that as the entrepreneur. I think it’s important to also separate that excitement from the metrics, your goals and how you’re really doing, and taking a critical eye to how things are going. For us, we started out with the idea of messaging in text, but we were going to use it for communication inside of a workforce, as well as communicating with customers. I did over 100 demos of that product, and the communication with customers was what was clearly resonating the most, so that’s really where we decided to focus our business.

I think secondly, to me, within at least the enterprise software world — and I think this can apply a little more broadly, but it certainly is true of enterprise software — there are three types of software: There’s software that helps companies to make more money, there’s software that helps companies to save money, and then there’s software that you’re not really sure what it does, but it doesn’t make or save money directly, but it solves some problem. From a difficulty basis, I think that the easiest thing to grow and sell and to make really successful is almost always bucket number one, things that help companies to drive revenue, drive growth. That’s what they’re trying to do, that’s their purpose.

That’s not to say that there aren’t great businesses built that help companies save money or that help companies to solve other problems that are less related to revenue. There’s great companies that do two and three. I think it’s just much harder. So doing the thing that’s number one, helping companies drive revenue and hearing this feedback from the market, just has made it easier for us.

Yeah, no, it makes sense. And you’ve obviously gravitated towards that first bucket with both of your businesses. When you guys were starting, based on the success of TapCommerce and having spent time as a leader at Twitter, you guys could have raised money from anyone. Why’d you choose to work with us again? This is an obvious puff-up question.

Well, I think that we had such a great experience working with you personally, as well as the extended Eniac partner team. I recall sitting down with my co-founders, and we looked at all the different offers we had, and we said, “Why are we going to make this harder to ourself? Why take risk and work with folks that we haven’t worked with before and don’t know? We already love the people we worked with before, and it’s a great opportunity to just do that again.” I would add to that we didn’t decide to work with everyone that we had worked with before, because we didn’t have the best experience with everyone. But we had a really fantastic experience with Eniac, and that’s why we chose to partner again.

Awesome. I obviously really appreciate that and feel very humbled that you guys chose to work with us again. This has been a really fast growth company. You guys have gone from three people to a pretty large organization, having raised quite a bit of money and very fast growth. Tell us about some of those major inflection points along the way. Where were those kind of kinks in the curve?

So as you mentioned, we started the company in September 2016 with a handful of people, and now we’ve got about 700-and-something people that work at the company, and we’ll probably be over 1,000 by the end of this year. So yeah, in about four and a half years, we’ve grown to a pretty significant scale, and certainly, that’s come with its bumps along the way. In terms of what those inflection points are, I think coming back to your earlier question around when you know something is working, product-market fit, when we were first taking our product to market, very few companies were using messaging, using text in order to communicate with customers. When we went out to sell it, people were interested, but they certainly weren’t actively looking for solutions in this area like they are today.

Sure.

It was very much a evangelical type pitch that you had to sort of really push the idea. I think that the turning point for us the first time, sort of the first phase there, was when we were running our first programs for customers, and we solved those programs, achieving our big target metrics, and we knew that it would qualify as a product that would make more revenue for them. It was clearly making a lot more revenue. When we saw that happening, I think that was probably the first sort of true inflection point for us, when we went from saying, “Are we doing the right thing?” to “We’re doing the right thing, we just need to invest in it and get ahead of it because we think we’re actually pretty early for this market.” So that was the first one.

I think the second one was probably a year-and-a-half later in the run-up to holiday of 2018, into 2019, where we just saw a tremendous increase in interest from customers. What happened was we had a couple cool cutting-edge brands that were using us during the holiday season, and other brands saw them doing it and they said, “Oh, well, there’s other people doing this. That’s pretty cool. We should do that too.” I think that sort of natural marketing of another brand doing it, we should do it too, that sort of fear of missing out, was the accelerant for our second phase there.

Got it. Cool. You mentioned bumps along the way. Anytime you’re going from, again, like three people to 1,000 people in five years, and the maturity level that you guys are at in terms of a business, there’s going to be challenges along the way, especially with that type of rapid scaling. Share some of those challenges that could be helpful for other founders out there.

I think the biggest question that you ask yourself sometimes, we actually talked about this this morning, is like, “So, is X problem a normal problem for companies like this? That this just happens and you have these issues and you just deal with them, and that’s just what it is like to be at the scale that we’re at? Or is this unique to us in any certain way?” Because I think that’s probably the biggest thing. Because you just see different types of problems, and you’re trying to see, “Are these normal problems or is this just really weird for us?” I think is the first thing that you ask around your community and figure out what the issue is.

I think that there’s certainly a factor here too that I think ups the difficulty a little bit, with it all being remote. Since we’ve been remote, we’ve went from a company of about 170 people to 700. So, most of the people have never been to the office or met anyone at the company. We’re lucky in that, I think, because we have the original 170, they act as a connective tissue between the company. If we didn’t have that at all, I think that’d be challenging. And it’s not just the remote workforce idea, I think it’s just the idea that even if you’re remote, doing some things in person, doing some meetings, being able to make some connections there is required, even if your company predominantly works remotely.

That’s incredible. You’ve 4x’d during COVID in terms of the team. How have you thought about establishing a sense of community within the organization and culture within the organization during that time given the remote circumstances?

Well, it’s very hard. We try to over-communicate. We were doing weekly all-hands for a long time, now we do them biweekly. I send out a lot of messages to the team about things that are going on. We have someone who sends out basically department-level updates on everything happening in each department to the entire company as like a three page summary every week. We also have an internal events person that’s been running events across divisions and teams, and doing all sorts of virtual events and virtual meetups and random coffees. So we’ve done a lot of things. It still doesn’t get to where you would normally be at meeting in-person and doing in-person stuff, but hopefully it’ll get us across across to where that will be in the coming quarters.

Got it. No, that makes sense. And then, what can you tell us about where Attentive’s going, going forward? What do you think the business looks like in five, seven years out?

As I noted a little earlier, I think that businesses are going to be expected to have a way for consumers to communicate with them in a reliable two-way, personalized way, and we want to be able to deliver that for all businesses that are working with consumers globally. We have a bent towards businesses that are selling something to the consumer that can be sold digitally, whether that has to be something that is then shipped to the consumer or is a digital good, or even they buy it and then they go pick up their burger in person; that’s all great. I think the point is just our focus, again, is around that idea of driving revenue for the business. If you’re driving some sort of digital sale, which the majority of businesses are, then it’s a lot easier to show that you’re driving those sales, and I like that direct connection to driving the sale.

Yep. That makes sense. And then I have a feeling we probably have a lot of founders, aspiring founders, folks really just starting out right now with us today. Having started now two successful businesses, what’s one piece of advice you would have for folks just starting out right now as founders?

I think that you can’t spend too much time talking to your customers, whether that is a business like ours, that’s selling to other businesses and selling SaaS software, or if you’ve got a consumer-facing product, whatever it might be, whatever vertical it is, I think you’ve got to find your customers and you’ve just got to talk to them and continue to get their feedback and learning what they want. Especially customers that are more wanting to innovate and pushing to innovate and on the cutting edge, that’s really, for us, helped shape our product roadmap, what we do, what we hear, all that sort of stuff. So I think that’s the thing. Where I’ve seen businesses run into issues at the earliest stage is when they spend a lot of time building, but not enough time pitching that product and really getting it.

And then secondly, I think trying to add some objectivity to the go-out-there-and-pitch-it process is important. Just, I guess, a couple of simple things: One, when going out and pitching your product, maybe you’re going out, you’re talking to folks and you want to get them to try to see if they would use your product, I like to end it with a quick survey, where we say, “Okay, great. Thanks so much. On a scale from one to 10, one being not at all interested, 10 being sign me up today and I will pay for this, I’m first in line and I will pay for this, how would you rate your level of interest in the product?”

Because a clear number rating often is very different, but gives a lot more clarity than what you thought you heard in the conversation. People tend to hear often what they want to hear. You’ll go through a conversation and you’ll say, “Wow, this person is so interested. Oh man, they’re so excited to get into this product.” And then you’re like, “Give it a score of one through 10.” And you’re like, “This guy is going to say a 10.” And it’s like, “No, we’re going to give it a six. It’s a six.” And you’re like, “Oh, okay. Why is it a six?” And then you hear the real feedback, right?

Yup.

You hear the real feedback after you get that rating. So we’ve been doing that for a while, and I think it adds a lot more clarity and it also uncovers what the real issues are. Why do you need to do that? It’s not because people lie to you. That’s not the reason. Most people are inherently very courteous, very nice. Most people don’t want to hurt your feelings, most people don’t want to create conflict, especially if they’re a friend of yours or something like that. So they’re not going to be forefront with their feedback and their harsh critical thoughts. They’re just going to say, “That sounds great. That sounds great.” But you have to press them to understand what are the real issues and how they really rank it. I think if we had done that even earlier on, we would have figured things out a little faster, and it helps us tremendously now.

That’s great. Very tangible and actionable advice. Well, that’s it. Thank you so much for joining us, but even more for choosing to work with Eniac a second time. Really appreciate it. Thank you.

Thanks very much, Hadley. We wouldn’t be here without your help and support and guidance. I also thank the extended Eniac family for their overall help in getting our business off the ground to where it is. We wouldn’t be here without you, so thank you. You guys are lucky to work with such a great firm.