Two Key Tips to Scaling 1:1 Customer Conversations in the Digital Age – A Conversation with Angel Investor Andy Payne

Andy Payne

You might think you need a crystal ball to predict the future, but sometimes you just need to look at what’s worked in the past.

Andy Payne has some valuable experience. Throughout his career, he’s been “bleeding edge early” on many fronts, including his first post-college gig at Digital Equipment Corporation (DEC) where he helped bring NCSA Mosaic – the first graphical web browser – into that company. He also co-founded one of the first eCommerce companies (Open Market), which became the predecessor of the modern shopping cart.

When people ask him where his office is today, Andy tells them it’s the MBTA Red Line between Harvard Square and South Station. As an angel investor, he’s always on the go – meeting with entrepreneurs and advising early-stage startups.

Because Andy is also a Drift advisor, I had the opportunity to pick his brain. We talked about his “Wild West” experiences, his best marketing advice, and what he sees coming down the pike for startups.

The Early Concept of “Dialog Marketing”

“Open Market was about making online transactions secure,” Andy says. “The next company I founded – Revenio – acknowledged that online transactions were just the table stakes. Our next big challenge was solving the marketing problem.”

Andy’s team saw marketing in a non-traditional way – not broken down into distinct campaigns and isolated interactions, but as a continuum. “Our take was that marketing was an ongoing, long-running discussion with customers,” he says. “It’s a brand/customer relationship that spans all the channels – a website, a phone call, a direct mail piece, and so forth.”

To describe this new vision, Revenio coined the term “dialog marketing” to encompass the ongoing exchange with customers across a variety of touch points.

While a lot has changed since the early days when Andy and his team were helping early-adopter legacy companies figure out how to integrate the internet and email into their existing marketing strategies, the concept of marketing as a relationship is one that seems to be coming back into its own.

Andy’s Top Two Marketing Tips

Andy takes a tough-love approach with the founders of early-stage startups to make sure they’re ready to handle the brutal reality of a competitive market. He shared two of his most-repeated pieces of marketing advice:

Tip #1: Don’t fall into the common traps.

“Most entrepreneurs are really strong in either their product vision or their technical ability (and sometimes both),” Andy says. “But they have no clue about customer acquisition or marketing.”

This causes many well-intentioned startups to make beginner mistakes:

  • Believing in the myth of build-it-and-they-will-come (a strategy that works just often enough to seem viable)
  • Trying to spend their way out of the problem (gone are the days when you could move the needle by buying clicks on Google)
  • Failing to install a digital marketing native on the team (“When a company has missing DNA, I can give the same advice over and over, eight hours a day, and it still won’t sink in.”)

What companies need to do is some good, old-fashioned blocking and tackling. It’s about crawling before you walk and walking before you run.

Tip #2: Test, test, and then test some more.

And how does a company go from crawling to walking? It’s all about experimentation and testing.

“Every company is unique and has custom problems and opportunities,” Andy says. “As they’re scaling their business, it’s all about fast, iterative testing and measurement.”

Back in the day, a company would have to spend substantial cash and wait six to eight weeks to get feedback on a direct mail print campaign. Today, running digital experiments is pretty cheap, and – thanks to the magic of technology – the results of those experiments are practically instantaneous and can be measured down to an incredible level of detail. Companies that succeed use these tools to move fast, learn fast, and evolve quickly.

New Market, New Tools, New Possibilities

You know what else moves fast? Technology. What worked yesterday, won’t work today, so we wind up in a kind of arms race as everyone rushes to adopt the latest shiny object.

“Email worked until it didn’t,” Andy says. “And not long ago you could publish a couple key blog posts to get a top listing in Google search, but not anymore.”

What Andy sees happening in today’s market has a lot to do with the “dialog marketing” he developed back in his Revenio days. “Before all this technology existed, we did business with people and we did it face to face,” he says. “Now we’re trying to find the modern reenactment of that on the internet.”

Andy gives the example of a fast-food company knowing your order in the same way the barista at your local coffee shop knows your drink order, “It’s not rocket science for the fast-food company to give you a way to order the same thing you ordered last time.”

“We tossed the personal piece out of the marketing equation,” he says. “And now, we’re bringing it back.”

Like with Drift and Conversational Marketing, Andy’s concept of dialog marketing as a long-running, two-way relationship with the customer not only provides a better customer experience, but also delivers valuable customer insights.

“A lot of entrepreneurs and investors spend a lot of time and money trying to reverse engineer why someone clicked on something,” Andy explains.

What people are trying to unlock is the power of intent. Did someone click a link because they are interested in a product for themselves, because they’re considering it as a gift, or some other reason entirely?

“If you really want to figure out intent and have a relationship with the customer, you’ve got to be able to hear more than just web clicks,” Andy says. “That’s what conversational marketing is all about.”

What’s Old is New Again

“We’re going to come full circle, and all those 70s fashions might come back into vogue,” Andy says. “Likewise, mailing somebody a piece of paper could become a novelty.”

He might be onto something.

Salesforce’s LetterFriend product enables the sending of handwritten notes as part of what the company refers to as an “armor-piercing” marketing strategy. Airbnb just launched a print magazine, and it’s quite impressive. And Amazon started mailing out printed catalogues for this holiday season.

“When companies get to a certain weight class, they can decide to use a conventional channel to augment their story,” Andy says. It’s an interesting way to stand out.

Likewise, there’s a movement toward engaging customers in 1:1 conversations. The overwhelming volume of marketing content demands a different kind of interaction, something that surprises people and makes them feel like they are really being seen and heard.

As Andy said, the world comes full circle. Treating people like people is back in fashion.

Ready for more insights? Check out the full interview with Andy here 👇

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