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Flexport releases onslaught of AI tools in a move inspired by ‘Founder Mode’

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Freight forwarding and logistics company Flexport is rolling out a suite of new products and features, many of which use AI, in what the company says will be the first in a series of semi-annual announcements of this kind. 

If that sounds similar to Airbnb’s approach to seasonal product announcements, that’s because it was the inspiration for Flexport’s new approach. 

“Brian Chesky told me to do it,” Flexport founder Ryan Petersen said in an interview, referring to Airbnb’s CEO. “He gave this great talk that Paul Graham wrote an essay about, called ‘Founder Mode,’ I was there that day, and he gave some great advice.” 

The next product release will come in “late summer,” according to Flexport.

Petersen told TechCrunch that moving to a twice-a-year “release” cadence offers two big benefits. One, he said, is “there’s nothing like the power of a deadline.” The other is more about marketing.

“We’ve developed a lot of great technology over the years, but it kind of comes out incrementally. There’s not a lot of fanfare, and buzz, and opportunity to tell the story in ways that customers can see what you’ve done, what you’ve built,” Petersen told TechCrunch.

Flexport says it is launching more than 20 different products on Monday, many of which it was already using internally, all powered by a combination of AI from OpenAI, Anthropic, and AWS. The big product promotion comes as Petersen completed his first full year back as Flexport’s CEO after firing former Amazon executive Dave Clark in late 2023 in a bid to “get [Flexport’s] house in order.”

Among the new products is Flexport Intelligence, which lets businesses get information about their shipments using natural language prompts. Another, called Control Tower, will give customers “real-time visibility and control over their entire logistics network, even on freight not managed by Flexport,” according to the company.

Previously, these were things that Flexport staff did for its customers. Leaning on AI to perform these tasks and, in essence, mediate that relationship is a big change for the company – especially because one of the reasons Petersen fired Clark was because he felt the company had devalued its customer relationships.

“This is something we’re really conscious about. I’m still a huge believer in ‘people first,’” Petersen said. He said the new products will offer “the best of both worlds” because businesses will still have the ability to call a Flexport team member – ideally, someone who knows them well – and get help if they need or prefer it that way. 

To that end, Petersen said he expects embracing AI will help Flexport grow its ranks, not replace workers. 

“I think that the company – and I think it’s going to be us – but the company that does the best job of automating this work will not have less workers. You’ll have more because you’re going to grow so fast. If you’re cheaper than other people, you’re going to need more people than ever to do service, sales, consulting, technology, development, et cetera,” he said.

Another effort Flexport announced Monday is the inclusion of AI-powered voice agents in some of its own workflows. 

Petersen stressed that Flexport is cautiously introducing this capability. Right now the company is testing this with the truckers and warehouses that use its logistics platform. The AI voice agent calls drivers to tell them there are loads available to be picked up in their area and calls warehouses to verify basic details like hours of operation.

Petersen said this helps with these simple conversations but that Flexport is still closing out these transactions through the regular workflow on its platform. He said he’s “hesitant” to rush to include voice agents in other parts of Flexport’s business until the capability and reliability improve. 

“My standard quality bar for making these things customer-facing is really high,” he said. “I think there is a future where customers will be happy talking to an AI if it’s really good at answering their question.” 

That doesn’t mean Petersen plans to move slowly with AI overall. In fact, he said he loves the speed at which Flexport has been able to experiment.

“Our teams can look at any place of [customer] pain and find some process that can be done better by an LLM or other form of machine learning, and just do it. And the next day, it’s live, it’s being used by thousands of companies without having to go sign enterprise contracts or beg people,” he said.



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