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Home»AI in Business»Flip Raises $20 Million in Series A for Its Verticalized Approach to AI-Driven Customer Service
AI in Business

Flip Raises $20 Million in Series A for Its Verticalized Approach to AI-Driven Customer Service

January 14, 2026005 Mins Read
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Returna startup that claims to offer a Amazon The Alexa-like voice AI experience for businesses has raised $20 million in a Series A funding round, he exclusively told Crunchbase News.

CEO Brian Schiff and CRO Sam Krut met ten years ago at university and started building different businesses together. After some changes, they raised funding for New York-based Flip in 2018, with the goal of creating AI that “automatically responds and resolves routine inquiries” from customers calling various businesses. They started by focusing on transportation companies and moved into retail in 2021 and healthcare in 2024.

AI-powered customer service is a saturated space, but Schiff says Flip’s approach is differentiated because it’s a very vertical approach focused on just three industries.

Brian Schiff and Sam Krut, co-founders of Flip. (Courtesy photo)
Brian Schiff and Sam Krut, co-founders of Flip. (Courtesy photo)

“While horizontal industry-agnostic ‘platforms’ require a custom experience and integration, vertical players like Flip come ready-made with everything brands in this industry need,” Schiff told Crunchbase News.

Among vertical players, Schiff says Flip has an advantage because its AI “is tested on over 300 million phone calls.”

Upcoming Coastal Ventures And Ridge Ventures co-led the round for Flip, which claims to have raised a total of $31 million in funding. Data Point Capital also participated in the tour, alongside ScOp Venture capital, Bullpen Capital, Business Forum and a group of angel investors. Flip declined to reveal the valuation, saying only that it was 3 times higher than its capital increase.

Year-over-year growth

Today, Flip has hundreds of business customers, including Under Armor, Tory Burch, Brands Newell and global shipping companies. The company achieved eight-figure ARR, with 3x year-over-year growth, according to Schiff.

Interestingly, the idea for Flip originated when Schiff and Krut were students at Cornell University. They had created a ride-sharing app called Red Route to hail taxis in Cornell, at a time when Uber was still banned in upstate New York. It was during this experience that they came up with the idea for what is today Flip.

“Customer service is one of the obvious categories of AI for businesses, and we talk daily and weekly with the biggest brands on the planet,” Schiff said. “Even for them, the question is not whether. It’s a question of “when” and “with whom”.

This, he said, created “an enormous amount of noise” in the market.

Over the past year, a number of what Schiff described as “generic AI vendors” have emerged.

“The great irony of this space right now is that while all the headlines and a lot of the funding have gone into these generic platforms that are trying to be AI all things to all people, in every industry, every channel, every use case. In reality, most of the real traction, most of the successful customer stories, are working with vendors like Flip that are very deeply involved in one or more specific industries,” Schiff told Crunchbase News in a interview.

Another differentiator, he says, is that few companies have developed deep expertise in AI phone customer service.

“Most people do this using chatbots or email autoresponders,” he said. “We pay close attention to the quality of the experience. No matter how nice it is to talk, it’s just another robot that stops the customer from trying to solve their problem.”

When it comes to the revenue model, Flip does not charge an upfront cost or require a long-term commitment. Instead, it charges per robocall – a usage model it has implemented since its inception.

“A vertical approach gives the best results”

Alex Rosenmanaging partner at Ridge Venturesbelieves that customer service is one of the few large markets where generative AI has produced tangible results for enterprise customers and a better experience for users.

“Based on our 30 years of investing in software, we believe a vertical approach yields the best results,” he wrote by email. “Flip has taken a different approach than many others by focusing on a few verticals and going very deep… Even though many competitors are making noise, some are going after different parts of the market, and Flip has quietly, so far, launched more live, large-scale customer deployments than anyone else. »

Mike Smerkloco-founder and CEO of Upcoming Coastal Venturessaid he has spent nearly two decades in and around call centers and voice technologies and has “never seen a more compelling ROI for customers” than what Flip offers.

He added: “The founding team is exceptional, customer feedback has been tremendous and the potential for Flip to become a billion-dollar company is clear. »

Smerklo also said he was impressed by the company’s approach to growth, which prioritizes capital efficiency.

“Several other companies that have raised enormously more money have to rely on ‘forward engineering’ to make their products work for customers,” he said. “Flip’s solution works, doesn’t require a massive investment from customers, and solves real and important business problems. »

Related Crunchbase query:

Illustration: Dom Guzman

Stay up to date on recent funding rounds, acquisitions and more with the Crunchbase Daily.

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