The Real Housewives of Tech Marketing

Drift thrives by acting less like a software company and more like a reality TV show. Here’s how to follow their lead.

Andy Raskin
Jul 19, 2018 · 10 min read

Embarrassing, but true: I know more about the daily lives, hopes and dreams of some employees at Drift—the Boston-based sales and marketing software company that’s raised over $107 million in VC cash—than those of some of my closest family members.

Of course, I’ve barely spent time with anyone at Drift. (I was a speaker at one of their events last year, and have no stake in the company.) Yet I know, for example, that Madelyn Ligtenberg, a Drift salesperson, loves chatting with prospects through Linkedin Messenger, and that she goes by “Mads.” I know that product lead Maggie Crowley built a chatbot tool based on mockups drawn by customers, that she has a tattoo on her left forearm, and that she blushes when colleagues call her a “big deal.” I know that everyone at Drift earns a monthlong sabbatical every three years and that CEO David Cancel is currently taking his, using the time to become a better horse hand for his daughter (who I know rides competitively), to cycle, and to meditate. I know that his meditation coach is named Brad.

How do I know these things? Because Drift follows an approach to marketing unlike any other company’s, opening up a window — through a stream of videos, podcasts, and social posts — into the real lives of its employees, customers, and extended community members. Recently, I summed up Drift’s approach in a tweet:

Drift VP of marketing Dave Gerhardt responded, in typical fashion, with a video he shot while walking down a Boston street, sipping vegetables through a straw. In it, he confirmed that it’s no accident I know all of these things about Drift’s team; in fact, the “reality show” is a deliberate strategy:

Every sales rep is going to tell me that their thing is faster, it’s better, it’s easier to use, so I don’t know who to trust. So as a company you really only have one choice to compete today. That’s to be real, it’s to be authentic, to be human.

It’s a choice that seems to have served Drift well. Despite operating in a space crowded with competitors, Drift has built huge brand awareness among target buyers: there isn’t a B2B team I meet today that isn’t at least thinking about Drift. In April, the company announced a $60 million Series C round led by Sequoia, and, just a few weeks ago, Gartner named Drift a “cool vendor” in a new category it’s calling “conversational marketing”—a moniker that Drift itself coined.

As a result, countless people—including several venture-backed CEOs—have told me that my back-and-forth with Gerhardt made them see the light, and that, going forward, they plan to invest more in video, audio, and social. One told me he was on the hunt for “our own Dave Gerhardt” so we can “push out more content.”

But if you think that all you need to achieve Drift’s success is to let the cameras roll and fill your social feeds with posts brimming with personal factoids, think again. Specifically, here are the 3 things Drift does incredibly well, and that every team should emulate:

#1. Celebrate Believers

Gerhardt’s point about how buyers can’t trust your “faster, better, easier” claims reminded me of a great Steve Jobs video. Having just returned to Apple, Jobs rips the marketing department a new one:

Jobs implicitly criticizes Apple’s branding strategy during his absence:

We need to bring [the Apple brand] back. The way to do that is not to talk about speeds and feeds. It’s not to talk about MIPS and megahertz. It’s not to talk about why we’re better than Windows.

Jobs and Gerhardt are attacking an approach to strategic messaging that I call the Differentiation Brag. It’s what most companies do because it seems like a reasonable way to answer “Why us?” In fact, marketing academics hold up Differentiation Bragging as best-practice for all company messaging; they even teach MBAs a framework for structuring your Differentiation Brag—if you’ve been part of any leadership team over the past 25 years, you’ll recognize it as the “positioning statement”:

For [target customer description…]…our product is a [product category] that provides [compelling reason to buy]. Unlike [the product alternative], we have assembled [key features…].

Perhaps a Differentiation Brag/positioning statement works if buyers have so few choices that they can be expected to take the time to evaluate out whose claims hold water. But as Gerhardt points out, most buyers today are bombarded by Differentiation Brags. That’s because, no matter what market you’re in, the set of competitors probably looks something like this:

How do you differentiate then, if not through claims of superiority? In the video I referenced earlier, Jobs hails Nike as “one of the greatest marketing jobs the world has ever seen.” He points out that Nike never stoops to a Differentiation Brag:

“They don’t ever tell you about their air soles, and why they’re better than Reebok’s air soles.”

What does Nike do instead? As Jobs explains:

“They honor great athletes, and they honor great athletics. That’s who they are. That’s what they’re about.”

In other words, Nike—like all great brand builders—celebrates people who believe in a story about how one finds fulfillment.

That’s why reality shows are a great model for brand-building: they do the same thing. Keeping Up With the Kardashians honors believers in fulfillment through celebrity and wealth. The Bachelor honors believers in fulfillment through finding the right mate. Fixer Upper honors believers in fulfillment through finding the right home (especially if Joanna Gaines designs it).

Drift honors believers in a story about closing more deals—“fulfillment” for salespeople and marketers—by engaging with buyers instantly and on their terms, rather than hiding behind traditional barriers like lead forms. One of my favorite episodes in the Drift “show” is not a video, but a blog post that celebrates sales operations professionals — not the most glamorous role in most teams. In a text introduction to the graphic below, Drift praises these people as the unsung heroes of “customer-centric” selling:

The believers you celebrate should also include your own team members. After all, every reality show needs recurring characters with whom its viewers can form attachments. In an unscripted video series called “Office Hours,” Gerhardt interviewed Drift sales rep Tanner Maguire, who had been on the job less than 3 weeks, about Drift’s “book a meeting with me” bot. You can really see Maguire loves this thing, and that he’s become a believer in Drift’s approach:

#2. Embrace the Unmeasurable

It’s been fascinating to watch as the cost of video production has plummeted over the last 25 years. In the early 1990s, I worked as a production coordinator for Japanese TV crews in New York, editing shows on videotape machines that cost hundreds of thousands of dollars (not to mention the rates of union members authorized to touch them). A few years later, during downtime between management consulting gigs, I worked as a digital video editor at CNN, where I assembled three-minute segments on a $35,000 Avid (a souped-up Mac with a massive-for-the-time 10GB hard drive). Today you can buy Final Cut Pro in the Mac App store for $300, and you’re good to go.

Video is obviously the most powerful medium when it comes to building a reality show—that is, for celebrating believers—yet many leaders underestimate it due to membership in what I’ll call the Cult of the Measurable. Now that so many sales and marketing activities can be measured—with multi-touch formulas attributing revenue (even profit) to each—many teams increasingly perform only activities where they can track the buyer journey. It’s like deciding that, because you own a Fitbit for counting your steps, the best way to get from New York to Mumbai would be to walk.

Measurable activities are great, but to succeed with a Drift-style reality show, you have to make peace with the idea that not everything you do will be directly traceable to a result. In January 2016, nearly two years before Drift would raise its $30 million Series B round, Cancel and Gerhardt launched a podcast, Seeking Wisdom, in which they gather smarts from industry (and non-industry) luminaries. How do you measure the value of these podcasts, which connect with target buyers, who want the tips, and build phenomenal brand associations through influencer guests?

A year later, when Drift still had only around 50 employees, Cancel created a department called “Drift Studio”—initially just a full-time videographer and an intern—to bring video and audio capabilities in-house. (I’m guessing most people at companies that size who are reading this are a long way from having those skills on staff.) As a result, Drift can honor believers in fancier ways, as in this video about a salesperson who gets pinged on her Apple Watch about meetings scheduled by her bot while she‘s out for a run:

…or this video celebrating Drift’s recent crop of interns:

Still, if you go down this path, someone will ask you to justify the ROI. You can respond with my Fitbit analogy about walking to Mumbai, or you could respond the way Gary Vaynerchuk does:

#3. Invite others to participate in the show

Gerhardt tells me that most of Drift’s best-performing videos are shot not on specialized equipment but on smartphones. That was true of his response to my tweet, as well as this video, posted to Linkedin and Twitter, in which he questioned common wisdom that you shouldn’t bother marketing to people during a holiday week:

Videos like these are the life blood of Drift’s reality show because they’re spontaneous and unpolished, but more importantly because they let audiences participate. Participation can happen through likes and comments (the video above yielded 260 interactions on Linkedin alone, for what seems like minimal investment in time and money) or when others are inspired to create reaction videos. The most impressive example of the latter was the recent Drift Sales Challenge, during which Drift employees were charged with recording videos about an old sales technique they had abandoned and new ones they had adopted. Some, like CFO Jim Kelliher and salesperson Derek Kelliher—who are apparently related but don’t say how—turned to Drift Studios to produce their response:

Other Drift employees took matters into their own hands, uploading video straight from their smartphones, like this one (that’s Mads on the left, with Drift sales colleague Jordan Pal):

Each person who accepted the challenge in turn challenged others to participate by name-checking them in social posts, the result being that for several days virtually every other post in my Linkedin feed was a Drift Sales Challenge video:

Ultimately, a reality show is a great metaphor for branding because both sell belonging

One of the joys of the Real Housewives is deepening your attachment to the show by tuning in to Watch What Happens Live with Andy Cohen, in which Cohen and his guests dish on recent episodes and takes sides in the cast’s latest battles.

Perhaps one day someone will produce a version of Cohen’s show about Drift, in which guests deconstruct Drift’s videos, podcasts, and posts. I hope they do, because even as a casual viewer, I have unanswered questions: How, exactly, are Jim and Derek Kelliher related? How did Drift’s marketing campaigns perform over the week of July 4th? Where is David Cancel taking his sabbatical, and did Brad, the meditation coach, travel with him? There are others.

The fact that I have these questions means that, like a budding reality show addict, I’m developing an attachment to the people at Drift. This aim of every successful show—whether it’s about bachelorettes, action heroes, or tech company employees—reminds me of a recent tweet by author and consultant Venkatesh Rao, in which he asserts that, deep down, buyers don’t want solutions to their problems. What they want is belonging:

Rao’s point, I think, is not that connecting to individuals is a waste of time, but that those connections are most effective in the context of a story about how a purchase grants membership in a desirable club. In this sense, the ultimate value of Drift’s “show” is in creating a club that its target buyers want to join.

In my work with CEOs, I help them align their leadership teams around a story that defines such a “club”—a story not about their companies or their products, but about how one thrives in the world now. Once we’ve nailed it, and it’s time to start telling it, I always suggest they look to Drift for inspiration. After all, there’s no better way to stoke people’s interest in joining a club than to have them get to know a bunch of its members.


About Andy Raskin:
I help CEOs align their leadership teams around a strategic story — to power success in sales, marketing, fundraising, product, and recruiting. My clients include teams backed by Andreessen Horowitz, KPCB, GV, and other top venture firms. I’ve also led strategic storytelling training at Salesforce, Square, Uber, Yelp, VMware and General Assembly. To learn more or get in touch, visit http://andyraskin.com.

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A network of business & tech podcasts designed to accelerate learning. Selected as “Best of 2018” by Apple. Mission.org

Andy Raskin

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Helping leaders tell strategic stories. Ex @skype @mashery @timeinc http://andyraskin.com

The Mission

A network of business & tech podcasts designed to accelerate learning. Selected as “Best of 2018” by Apple. Mission.org