IVP’s Hypergrowth Stories: How Attentive Changed the Conversation Between Companies and Customers

In IVP’s Hypergrowth Stories series, CEOs of the fastest-growing companies share their ins and outs of company building in the hypergrowth environment.

March 2020 marked a pivotal change in the way brands engage with their customers. Email inboxes were getting increasingly crowded with promotional messages and Instagram feeds were flooded with ads. With in-person shopping discouraged due to shelter-in-place policies, companies needed to find a new way to engage with customers in the competitive ecommerce landscape.

Enter Attentive. The platform helps brands cut through the noise and build trust with their subscribers using personalized, engaging text messages. Each message shares valuable information about sales, promotions, and new product launches, directly to a customer’s cell phone.

Launched in 2016, Attentive was founded by veterans of the mobile ecommerce space. Prior to founding Attentive, some of the co-founders founded TapCommerce, a mobile app retargeting company that was later acquired by Twitter. This experience left them uniquely qualified to recognize the value and potential of mobile communications with retail customers.

The company experienced massive growth over the past 18 months – Attentive had 200 employees at the beginning of 2020, and is now a remote-first workforce of 1,100 employees throughout the US. In 2020, Attentive generated over $4.5 billion in revenue for e-commerce brands. Attentive works with more than 4,000 brands, including CB2, Rebecca Minkoff, and Thirdlove, and is on track to drive over billions more in revenue for brands this year.

To date, Attentive has raised $863 million in funding. The company has been recognized for a number of accolades such as Inc.’s Best Workplaces of 2021, Forbes’ inaugural list of America’s Best Startup Employers for 2021, and most recently being ranked #3 on Deloitte Technology Fast500. Attentive achieved this ranking due to its massive revenue growth of 49,155% from 2017 to 2020 and ranked No. 1 fastest-growing company in the Tri-State region. This is just a peek at what Attentive has achieved in such a short amount of time.

Brian Long, who serves as CEO, discusses his experience navigating Attentive’s rapid growth while transitioning to the remote-first environment. We discussed how to hire, maintain the company culture and also ask the right people to identify your product-market fit.

This Q&A was edited for length and clarity.

How did Attentive shift into a remote work environment?

Like many companies in our space during the beginning of Covid, we had no idea what to do. We started as a company with a very office-focused culture. Now, almost two years later, we’re remote-first. This didn’t happen overnight, it was an adjustment for all. But we quickly began to recognize that we can be even more effective remotely than we were in person.

After we went remote, we really had no choice but to keep hiring. Over time, we realized just how efficient remote work and remote hiring were. Before, we were limited to looking at talent located in New York. Now, we can hire incredible talent located anywhere and that.

What does the future of Attentive’s remote culture look like to you?

To me, what remote first means is that when we’re considering any of our processes, we take it from a remote mindset at first. How would it be if we were a remote person going into this process? How do we handle onboarding? How do we handle teaching? How do we handle all this stuff where everything is done remotely? I think that the remote-first mindset is really central to our processes and culture – it’s still in progress for us.

I think now, being remote has really leveled the playing field so that all voices can be heard. Everyone’s kind of coming from the same level and I think that’s really great.

I also love how easy it is to collaborate. In documents we can actually all pitch in and work together. For example, in a meeting we can all post our answer at once, rather than wait for one person to speak and provide thoughts. I could hear from all eight people in a meeting at once and discuss it with a follow up. You can also see the history of what they say in the document and review that and remember a certain conversation. We have become much more efficient.

Are there any elements of your company culture from being in-person that you were able to take forward into being remote?

We used to open up our in-person meetings by sharing the wins and successes of different people on the team. We’ve brought those into our remote meetings, and they were crucial to keep up team morale and spirits, especially during such a challenging year.

I think it’s a great way to make sure that people are being appreciated and celebrated for their progress and successes. It’s sometimes easy to get negative and focus on the problems – but we have a team full of incredible problem-solvers. It’s important to acknowledge that there’s a lot that’s going well and that should be celebrated.

How have you been able to keep those startup style values alive in your culture, even as you’ve grown to this level?

I definitely still consider us a startup and I think that’s an important mindset. When you’re recruiting people, you are responsible for setting the mindset for the type of company you want this to be. We never want to get complacent, or forget the values of grit and tenacity that got us to where we are now. We want to remain nimble and strategic, and hire people that have that same mindset.

At times, people may think that we’re this big cruise ship and everything is on cruise control, but how can we grow from that type of mindset? So, we like to be really nimble and push that mindset so we can get ourselves to that next level.

What approach did you take to seek out talent that had that same mindset?

I think it’s making sure people know what they’re buying into.I always say look, this isn’t some big tech company where you hang your boots up and hang out for a couple of years. We want you to take big swings – if it succeeds, great. If it doesn’t, you learn from it. If you’re looking for more of a relaxed setting, this is the wrong place.

I call it a reverse sale or almost like a warning in an interview. I spoke with a candidate the other day and I said to them: heads up – this job is definitely a sprint and it’s very fast moving. Do not take this job if you have any trepidation over that. I really like to hammer that in. I want to make sure that they’re doing a job they want to do because different people are at different times in their lives. Maybe someone isn’t up for sprinting and isn’t looking for that setup.

What is your method for spotting trends early on and what advice would you give to other founders to find their product-market fit?

First off, you have to sell things, early and often. I still see so many entrepreneurs that are working away at something but they’re afraid to go and sell it. Secondly, I think they really have to sell it. I hear a lot of entrepreneurs say they’ve spoken to a few people that thought their product was great, so they continue to work on that same product because those people thought it was great. I think that’s a really dangerous thing because when you talk to someone with passion and excitement, the vast majority of people are going to respond with similar excitement, without actually wanting the product. I think it’s so easy to take that as a signal that you’re doing the right thing, when in reality, you get nothing from that. Because often people just say yes and say here’s the contract for $20,000 and they don’t follow through.

So again, sell early and often. Be skeptical, actually sell your product and really press to make sure you aren’t just getting a yes from a friendly person.

Did you get any no’s or people thinking your idea was crazy?

We had some other products we were selling at first and we sold a lot. I then fell into a curse of having a lot of friendly meetings that didn’t turn into contracts that people were willing to spend money on. We ultimately decided to pivot away from that. We were really focused on seeing if we could get initial people to test this, and if our product could actually make money.  Once you know what makes money, you then know how to get more people to use your product.

We didn’t have people jumping up and down for an SMS product, but we did meet people who wanted to make more money. We knew that our product could make more money for the customers who got to try it. So our story really just turned into making more money by doing this. Then that did really well.

Do you have any predictions for the future of retail and E-commerce? What can we expect to see in the future?

I think B2C businesses are going to want to sell their products directly to the consumer and do it online. Most of those businesses will be using text messaging as a way to communicate with their customers. Because there is so much value in that. Everyone has a mobile phone these days and they have quick access to it so the best way to reach an audience is by texting them.  More and more of these businesses are starting to see the advantages of that.

I also believe that we’ll be seeing a lot of brands that traditionally didn’t sell direct to consumer, start selling direct to consumer. There is so much innovation happening in the ways that companies engage with their customers – it’s really exciting to watch.