Jenny Fleiss, CEO of Rent The Runway and JetBlack, thinks that shopping has become a bit too...transactional.

Her argument: Sites like Amazon may make it easy to find the products you want online, but they've also made shopping itself into a chore. Even gift shopping, a process that should be thoughtful and considered has become yet another to-do in our increasingly busy lives. Online shopping's shrinking emotional stakes, she says, are driving more people to alternative shopping experiences that feel new and fresh. These alternatives include JetBlack, a still-stealthy service that offers customers personal shopper experiences via text message.

"I feel like some of the delight has been stripped from shopping," Fleiss said on stage at Button's TAP Summit earlier this month. "People are settling for a price that's fine, a product fit that's okay, and a delivery speed that's okay."

Missing, she argues, are digital shopping experiences that offer learning opportunities, genuine surprise-and-delight, and enjoyable interactions with real people. These ideas are, of course, built into the JetBlack user experience itself— and, so far, it's proven to be a successful formula. Fleiss said that the average JetBlack user spends $1,500 per month and that 75% of the service's customers are engaged with it at any given time.

Here are a few big takeaways from Fleiss' on-stage conversation with Button founder and CEO Michael Jaconi.

Startups live and die by timing

JetBlack may be a compelling idea, but it's not a new one. Webvan, a dot-com bubble attempt at on-demand delivery, filed for bankruptcy in 2001. A decade later came New York City startup WunWun, which offered a similar-sounding on-demand delivery service for three years before shutting down in 2015.

But Fleiss said that shifts in consumer behavior, combined with advances in voice-to-text technology, machine learning, and visual search tools have made the model more viable today than it was just a few years ago. "A lot of startup success is timing," she said. "Even with Rent The Runway, there were other businesses that attempted that model. There may be many things they did that were a little off, but timing played a big role, too."

Personalization is the future of conversational commerce

Search for "baby stroller" or any other product on Amazon, and you are likely to get thousands of research results with a dizzying array of variation between them. That dynamic is impossible in the world of conversational commerce, where results come in the form of texts or audio responses from devices like Amazon's Echo or Google Home. In those contexts "you have to get the results down to one or two— maybe three but that's about it," said Fleiss.

Personalization has been key to the strategy and success of Rent the Runway. In talking to users who hadn't rented from the service, the company found that many women were worried that the dresses they saw wouldn't be a good fit for their body types. To reduce this uncertainty, Rent the Runway started to collect photos and sizing information from women who had rented dresses from the service. This information was added to product review pages, which were personalized based on the size information of individual users. The impact of the move was felt quickly, with JetBlack seeing its conversations double overnight, according to Fleiss.

"However important personalization has been in the past, it will be exponentially more important because of conversational commerce," she said.

The direct-to-consumer economy should be a wake-up call to traditional marketers

Allbirds. Away. Casper. Buzzy direct-to-consumer startups are turning the traditional retail model on its head by developing new approaches to distribution, marketing, and partnerships. In many cases, these nimble companies have out maneuvered much larger competitors,

The DTC wave should encourage more companies to "evaluate their business strategies," said Fleiss. "We're in a moment where traditional marketing and having the biggest marketing budget doesn't matter as much as the community you can build, the experiences you can build around a brand, and the creative partnerships you can do."

"It makes it more challenging for everyone to up their game and gain marketshare. I think it's a really exciting moment for sure."